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Journal articles on the topic 'Pyridazine'

Author: Grafiati

Published: 4 June 2021

Last updated: 25 July 2025

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1

Deeb, Ali, Besher Bayoumy, Fathy Yasine, and Rida Fikry. "Pyridazine Derivatives and Related Compounds, Part 4. Pyrrolo[2,3-c]pyridazines and Furo[2,3-c]pyndazines, Synthesis and Some Reactions." Zeitschrift für Naturforschung B 47, no. 3 (1992): 418–23. http://dx.doi.org/10.1515/znb-1992-0320.

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Ethyl 5-amino-3,4-diphenyl-7H-pyrrolo[2,3-c]pyridazine-6-carboxylate (1), ethyl 5-aminofuro[ 2,3-c]pyridazine-6-carboxylate (2) and 5-aminofuro[2,3-c]pyridazine-6-carboxamide (3), are obtained from 4-cyano-5,6-diphenyl-3(2H)-pyridazinone. 5-Acetamido and 5-chloroacetamido derivatives prepared from 1, undergo cyclization on heating to form 2-substituted pyridazino[4',3':4,5]pyrrolo[3,2-d]oxazin-4(5H)-one (5a, b). The reaction of 1 and 2 with hydrazine gave 6-carbohydrazide derivatives (7 a, b). Compound 3 undergoes condensation with acetyl chloride, chloroacetyl chloride, benzoyl chloride, form

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2

Mohammad, Asif, Abida, and Tauquir Alam Md. "Diverse chemical and biological potentials of various pyridazine and pyridazinone derivatives." Chemistry International 5, no. 3 (2019): 206–31. https://doi.org/10.5281/zenodo.2525555.

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A series of heterocyclic compounds incorporating pyridazine moiety were for diverse biological activities. Pyridazines and pyridazinones derivatives showed wide spectrum of biological activities such as vasodialator, cardiotonic, anticonvulsant, antihypertensive, antimicrobial, anti-inflammatory, analgesic, anti-feedant, herbicidal,  and various other biological, agrochemical and industrial chemical activities. The results illustrated that the synthesized pyridazine/pyridazine compounds have diverse and significant biological activities. Mechanistic insights into the biological properties

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3

Barlin, GB. "Imidazo[1,2-B]Pyridazines. I. Some 3-Alkoxy-6-Halogeno-2-Phenyl-(and 4′-Substituted Phenyl)Imidazo[1,2-B]Pyridazines and 3-Methoxy-2,6-Diphenylimidazo[1,2-B]Pyridazine." Australian Journal of Chemistry 39, no. 11 (1986): 1803. http://dx.doi.org/10.1071/ch9861803.

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A series of 3-alkoxy-6-halogeno-2-phenyl(and 4′-substituted phenyl) imidazo [1,2-b] pyridazines (1) and 3-methoxy-2,6- diphenylimidazo [1,2-b] pyridazine have been prepared from the relevant pyridazin-3-amines and arylglyoxals, followed by O- alkylation of the corresponding imidazo [1,2-b]pyridazin-3(5H)-ones with diazoalkanes. 6- Chloro-3-methoxy-2-phenylimidazo[2,1-a] phthal-azine was prepared similarly.

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4

Barlin, GB, LP Davies, PW Harrison, NW Jacobsen, and AC Willis. "Imidazo[1,2-b]Pyridazines. XVI. Synthesis and Central Nervous System Activities of Some 6-(Chloro, Alkylthio, Phenylthio, Benzylthio or Pyridinylmethylthio)-3-(unsubstituted, benzamidomethyl or methoxy)-2-(styryl or benzoyl)imidazo[1,2-b]pyridazines." Australian Journal of Chemistry 47, no. 11 (1994): 1989. http://dx.doi.org/10.1071/ch9941989.

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Some 6-( chloro, alkylthio, phenylthio, benzylthio or pyridinylmethylthio )-3-( unsubstituted , benzamidomethyl or methoxy )-2-styrylimidazo[1,2-b] pyridazines and 6-chloro-3-( unsubstituted and benzamidomethyl )-2-benzoylimidazo[1,2-b] pyridazines have been prepared and tested for their ability to displace [3H]diazepam from rat brain plasma membranes. The structures of 6-chloro-2-benzoyl[and 6-fluoro-2-(4′-tolyl)] imidazo [1,2-b] pyridazine have been confirmed by X-ray analyses. The reactions of 6-methylthio(and 6-phenylthio)pyridazin-3-amines with 3-bromo-1-phenylpropane-1,2-dione also have

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5

M., Sumakanth, V. Malla Reddy, V. S. H. Krishnan, and B. S. Sastry. "Synthesis of Some New Imidazo[1,2-b] Pyridazines." International Journal of Pharmaceutical Sciences and Nanotechnology 2, no. 1 (2009): 471–76. http://dx.doi.org/10.37285/ijpsn.2009.2.1.14.

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Several 2,6-diaryl-imidazo[1,2-b]pyridazines (5 & 7) were prepared from 3-amino-6-aryl-pyridazines (3) which in turn were obtained from the corresponding 6-aryl-pyridazine-3(2H)-ones(1) via., 6-aryl-pyridazin-3(2H)-thiones (2) as intermediates, by a reaction with an appropriate a-halocarbonyl compounds (4) or a-haloacyl carbamates (6) in a suitable solvent at reflux temperature. The resulted products were characterized by their physical, analytical and spectral data.

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6

Kazimierczuk, Zygmunt, Jarosław Kamiński, and Flavio Meggio. "Studies on Improved Synthesis of 2'-Deoxyribonucleosides of Pyridazine Derivatives." Collection of Czechoslovak Chemical Communications 71, no. 6 (2006): 889–98. http://dx.doi.org/10.1135/cccc20060889.

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A number of 2'-deoxyribonucleosides of halogenated pyridazine derivatives were prepared by glycosylation of their respective potassium or DBU salts in acetone. The reaction yielded predominatly β-anomers that could be purified by simple crystallization or column chromatography. Of the studied pyridazines and deoxynucleosides, only 4-bromo-6-chloropyridazin-3-one and 6-chloro-2-(2'-deoxyribofuranosyl)pyridazin-3-one showed modest inhibition of CK2 kinase.

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7

Schmitt, Martine, Jean-Jacques Bourguignon, Gordon B. Barlin, and Les P. Davies. "Imidazo[1,2-b]pyridazines. XXIV Syntheses of Some 3-(Variously Substituted) Imidazo[1,2-b] pyridazines, 6-Substituted 2-Benzoyl- imidazo[1,2-b]pyridazines and Pyrimido[1,2-b]pyridazin- 5-ium-3-olates and their Interaction with Central and Mitochondrial Benzodiazepine Receptors." Australian Journal of Chemistry 50, no. 8 (1997): 779. http://dx.doi.org/10.1071/c97030.

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The syntheses of some ethyl 2-{2′-aryl-6′-(chloro, iodo and methoxy)imidazo[1,2-b]pyridazin-3′-yl}-2-(acetoxy, acylamino, hydroxy and methoxy)acetates, 6-methyl-2-(p-tolyl)- and 6-chloro-2-(4′-chlorophenyl)-3-trimethylammoniomethylimidazo[1,2-b]pyridazine iodides (and reactions thereof), 2-benzoyl 6-substituted imidazo[1,2-b]pyridazines and 7-(methoxy, chloro and phenylthio)-2-phenylpyrimido-[1,2-b]pyridazin-5-ium-3-olates are reported. The ability of these compounds to displace [3H]diazepam from rat forebrain membrane [central benzodiazepine receptor (BZR)] and rat kidney membrane [mitochondr

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8

Barlin, GB, LP Davies, SJ Ireland, and JK Zhang. "Imidazo[1,2-b]pyridazines. XIV. Syntheses and Central Nervous System Activities of Some 6-(Methoxy-, dimethoxy-, methylenedioxy-, chloro- and fluoro-)-3-alkoxy-2-phenyl(and substituted phenyl)imidazo[1,2-b]pyridazines." Australian Journal of Chemistry 46, no. 3 (1993): 353. http://dx.doi.org/10.1071/ch9930353.

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Syntheses are reported for 28 new 3-alkoxy-6-(3′-methoxy-,3′,4′-dimethoxy, 3′,4′-methylene-dioxy-, 2′- and 4′-chloro- and 4′-fluoro-benzylamino)-2-phenyl(and substituted phenyl) imidazo -[1,2-b] pyridazines from the corresponding 6-substituted pyridazin-3-amine 2-oxides with α- bromoacetophenones, followed by alkylation of the intermediate 3-hydroxyimidazo[1,2-b] pyridazines. In tests of the ability of these compounds to displace [3H]diazepam from rat brain membrane, 3-(2′-ethoxyethoxy)-6(3′-methoxybenzylamino)-2-phenyl- and 6(3′,4′-methylenedioxybenzylamino )-2-(3″,4″-methylenedioxyphenyl)-3-

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9

Sepsey Für, Csilla Sepsey, Gergő Riszter, Áron SzigetvárI, et al. "Novel Ring Systems: Spiro[Cycloalkane] Derivatives of Triazolo- and Tetrazolo-Pyridazines." Molecules 26, no. 8 (2021): 2140. http://dx.doi.org/10.3390/molecules26082140.

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In orderto synthesize new pyridazine derivatives anellated with different nitrogen heterocyclic moieties, spiro[cycloalkane]pyridazinones were transformed into the corresponding thioxo derivatives via a reaction with phosphorus pentasulfide. The reaction of the formed 2,3-diazaspiro[5.5] undec-3-ene-1-thiones with hydrazine provided the corresponding 1-hydrazono-2,3-diazaspiro[5.5] undec-3-ene, whose diazotization led to the desired spiro[cyclohexane-1,8′-tetrazolo[1,5-b]pyridazines. The reaction of dihydropyridazinethiones with benzhydrazide afforded the corresponding 7H-spiro[[1,2,4]triazolo

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10

Asif, Mohammad. "The Study of Pyridazine Compounds on Prostanoids: Inhibitors of COX, cAMP Phosphodiesterase, and TXA2Synthase." Journal of Chemistry 2014 (2014): 1–16. http://dx.doi.org/10.1155/2014/703238.

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The pyridazine moiety is an important structural feature of various pharmacological active compounds. Synthetic pyridazine compounds have been reported as effective antiprostaglandins (PGs), 5-lipoxygenase (5-LOX), and antiplatelet agents, that is, inhibitors of prostaglandin or cyclooxygenase (COX-I & COX-II) enzyme, platelet cAMP phosphodiesterase, and thromboxane A2 (TXA2) synthase. These compounds are selective and nonselective COX inhibitors and showed analgesic, anti-inflammatory, and antipyretic activity. Pyridazine compounds with antiplatelet agents inhibited TXA2enzyme. Pyridazine

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11

Barlin, GB, LP Davies, SJ Ireland, and JK Zhang. "Imidazo[1,2-b]pyridazines. XI. Syntheses and Central Nervous System Activities of Some 6-(N-Benzyl-N-methylamino)-3-methoxy-2-phenyl(and substituted phenyl)imidazo[1,2-b]pyridazines." Australian Journal of Chemistry 45, no. 4 (1992): 751. http://dx.doi.org/10.1071/ch9920751.

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Syntheses are reported for 196-(N-benzyl-N-methylamino )-3-methoxy-2-phenyl(and substituted phenyl or pyridinyl ) imidazo [1,2-b] pyridazines from 6-(N-benzyl-N-methylamino)pyridazin-3- amine 2-oxide. The ability of each of these compounds to displace [3H]diazepam from rat brain membrane preparations was measured and the IC50 values (or percentage displacements) are reported and discussed. 6-(N-Benzyl-N-methylamino )-3-methoxy-2-phenylimido[1,2-b]pyridine was about half as active as its 6-bemylamino analogue, and the most active compound was 6-(N-benzyl-N-methylamino )-2-(2'-fluorophenyl)-3-me

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12

El-Dean, Adel M. Kamal, Shaban M. Radwan, and Yasser A. Elosealy. "Synthesis of some new imidazo[3″,4″:1′,2′] pyrimido[4′,5′:4,5]thieno[2,3-c] pyridazines and other fused thieno[2,3-c]pyridazines." Journal of Chemical Research 2008, no. 11 (2008): 622–25. http://dx.doi.org/10.3184/030823408x371056.

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5-Amino-3,4-diphenylthieno[2,3-c]pyridazine-6-carboxamide was prepared and used as starting material to form the novel 6-chloromethyl-3,4-diphenylpyrimido[4′,5′:4,5]thieno[2,3-c]pyridazin-8(7H)-one (3), the 6-(arylaminomethyl) compounds (4a–c), 7-aryl-7,8-dihydro-3,4-diphenylimidazo[3″,4″:1′,2′]pyrimido[4′,5′:4,5]thieno[2,3-c]pyridazin-10(6H)-ones (5a–c), ethyl 7,8-dihydro-8-oxopyrimido[4′,5′:4,5]thieno[2,3-c]pyridazine-6-acetate (6) and its carbohydrazide (7). The pyridazinothienopyrimidotriazepinedione 8, pyridothienopyridazine 12 and pyridazinothienooxazepine 13 were also prepared.

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13

Abd El-Salam, Nasser M., Mohamed S. Mostafa, Gamal A. Ahmed, and Othman Y. Alothman. "Synthesis and Antimicrobial Activities of Some New Heterocyclic Compounds Based on 6-Chloropyridazine-3(2H)-thione." Journal of Chemistry 2013 (2013): 1–8. http://dx.doi.org/10.1155/2013/890617.

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Three tricyclic ring system, pyridazino[6,1-b]quinazolin-10-ones, benzimidazolo-pyridazine thione, and 1,2,4-benzotriazino-pyridazinethione along with imidazo-[1,2-b]-pyridazinethione, 1,2,4-triazolo[4,3-b]pyridazine-thione derivatives were synthesized starting from 6-chloropyridazin3-(2H)-thione. Some disulfide and sulfide derivatives were also prepared. The antimicrobial activity of the synthesized compounds was tested. Some of these compounds possess a highly response against gram-positive and gram-negative bacteria as well as fungi.

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14

Galtier, Christophe, Sylvie Mavel, Robert Snoeck, et al. "Synthesis and Antiviral Activities of 3-Aralkyl-Thiomethylimidazo[1,2-b]Pyridazine Derivatives." Antiviral Chemistry and Chemotherapy 14, no. 4 (2003): 177–82. http://dx.doi.org/10.1177/095632020301400402.

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The synthesis of novel substituted 3-aralkylth-iomethylimidazo[1,2- b]pyridazines is reported. All of the synthesized compounds are devoid of antiviral activity against the replication of human immunodeficiency virus. However, compounds 6-chloro-8-methyl-3-phenethylthioimidazo[1,2- b]pyridazine and 6-chloro-2-methyl-3-phenethyl-thioimidazo[1,2- b]pyridazine are potent inhibitors of the replication of human cytomegalovirus in vitro, while compounds 6-chloro-2-methyl-3-benzylthiomethylimidazo[1,2- b]pyridazine and 6-chloro-2-methyl-3-phenethyl-thioimidazo[1,2- b]pyridazineare inhibitors of the r

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15

Abdullah, Ahmad H., Jalal A. Zahra, Salim S. Sabri, et al. "Thiophene Ring-opening Reactions III: One-Pot Synthesis and Antitumor Activity of 1,3,4-Thiadiazoline–Benzothiazolo[3,2-b]pyridazine Hybrids†." Current Organic Synthesis 19, no. 2 (2022): 279–90. http://dx.doi.org/10.2174/1570179418666211109112148.

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Introduction: The preparation of model 6-chloro-5-nitrothieno[2,3-c]pyridazines incorporating (2'-halo-5'-nitrophenyl) entity is described. Interaction of these substrates with N'-(aryl)benzothiohydrazides, in the presence of triethylamine, followed a formal [4+1] annulation, furnishing the respective 1,3,4-thiadiazoline–benzothiazolo [3,2-b]pyridazine hybrids directly. This one-pot synthesis implies thiophene ring-opening and two consecutive intramolecular cyclizations. The structures of the synthesized new hybrids are supported by MS, NMR, and IR spectral data and further confirmed by single

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16

Heinisch, G., E. Huber, C. Leitner, et al. "Pyridazino[3,4-b][1,5]Benzodiazepin-5-Ones: Synthesis and Biological Evaluation." Antiviral Chemistry and Chemotherapy 8, no. 4 (1997): 371–79. http://dx.doi.org/10.1177/095632029700800410.

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Starting from 3,6-dichloropyridazine-4-carboxylic acid chloride, a series of pyridazino[3,4- b][1,5]benzodiazepin-5-ones bearing various substituents in positions 3, 6, 8 and 11 was prepared via N-alkyl-3-alkylamino-6-chloro- N-(2-chloro-5-nitrophenyl)-pyridazine-4-carboxamides. The latter were smoothly accessible by treatment of N-alkyl-3,6-dichloro-N-(2-fluorophenyl)-pyridazine-4-carboxamides with primary aliphatic amines. The new tricyclic compounds, which are structurally related to nevirapine and congeners were screened as human immunodeficiency virus type 1 reverse transcriptase inhibito

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17

Mendogralo, Elena Yu, Roman O. Shcherbakov, Ludmila N. Sorotskaja, and Maxim G. Uchuskin. "Pyrrolo[1,2-<em>b</em>]pyridazines: synthesis and application perspective." Mendeleev Communications 35, no. 3 (2025): 241–48. https://doi.org/10.71267/mencom.7749.

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Pyrrolo[1,2-<em>b</em>]pyridazines continue to attract significant interest due to their diverse biological activities. This review explores various synthetic approaches to constructing the pyrrolo[1,2-<em>b</em>]pyridazine scaffold and examines its applications. Covering key advancements in pyrrolo[1,2-<em>b</em>]pyridazine chemistry reported between 2008 and 2024, we highlight their role in the development of practically relevant compounds. By emphasizing recent progress in this field, we aim to inspire further research and innovation in the synthesis and

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18

Abdelrazek, Fathy M., Ahmed A. Fadda, and Akram N. Elsayed. "Novel Synthesis of Some New Pyridazine and Pyridazino[4,5-d]pyridazine Derivatives." Synthetic Communications 41, no. 8 (2011): 1119–26. http://dx.doi.org/10.1080/00397911003797809.

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19

Czech, Karin, Norbert Haider, and Gottfried Heinisch. "Pyridazines, LIV: On the synthesis of pyridazine-fused S-heterocycles: Thieno[2,3-c]pyridazine, pyrimido[4?,5?:4,5]thieno[2,3-c]pyridazine, and pyridazino[3,4-b][1,4]benzothiazine." Monatshefte f�r Chemie Chemical Monthly 122, no. 5 (1991): 413–18. http://dx.doi.org/10.1007/bf00809662.

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20

Wasfy, Ashraf A. F., Mohamed M. H. Arief, Mahassen S. Amine, Shafey G. Donia та Aly A. Aly. "γ-Oxo Carboxylic Acids in Heterocyclic Synthesis, III. Synthesis of Biologically Active 4-Benzylamino-6-(5,5-dioxodibenzothiophen- 2-yl)-2,3,4,5-tetrahydropyridazin-3-ones". Zeitschrift für Naturforschung B 57, № 6 (2002): 668–76. http://dx.doi.org/10.1515/znb-2002-0613.

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α-Benzylamino-β-(5,5-dioxodibenzothiophen-2-carbonyl)propionic acid (1) has been synthesized by treating the corresponding β-aroylacrylic acid with benzylamine in dry benzene. On treatment with hydrazine hydrate the keto acid 1 furnishes the corresponding pyridazinone derivative 2. The behaviour of 2 towards carbon electrophiles, namely, ethyl chloroacetate, acrylonitrile, formaldehyde and secondary amines (under Mannich reaction conditions), aromatic aldehydes and carbon nucleophiles, namely, POCl3/PCl3 and P2S5 has been investigated. The 3-chloropyridazine derivative 13 reacts with hydrazine

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21

CZECH, K., N. HAIDER, and G. HEINISCH. "ChemInform Abstract: Pyridazines. Part 54. Synthesis of Pyridazine-Fused S-Heterocycles: Thieno(2,3-c)pyridazine, Pyrimido(4′,5′:4,5)thieno(2,3-c)pyridazine, and Pyridazino(3,4-b)(1,4)benzothiazine." ChemInform 22, no. 35 (2010): no. http://dx.doi.org/10.1002/chin.199135173.

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22

Chmovzh, Timofey N., Karim S. Gaisin, and Oleg A. Rakitin. "5,6-Dihydro-[1,2,5]oxadiazolo[3,4-d]pyridazine-4,7-dione." Molbank 2023, no. 2 (2023): M1649. http://dx.doi.org/10.3390/m1649.

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1,2,5-Chalcogenadiazoles fused with electron-withdrawing heterocycles have been actively investigated for the preparation of organic photovoltaic materials. [1,2,5]Oxadiazolo[3,4-d]pyridazines are much less studied than other chalcogenadiazolopyridazines due to their low availability. In this communication, we report our study showing that 5,6-dihydro-[1,2,5]oxadiazolo[3,4-d]pyridazine-4,7-dione, a key precursor for the synthesis of 4,7-dihalo-[1,2,5]oxadiazolo[3,4-d]pyridazines, is formed via the cyclization of 1,2,5-oxadiazole-3,4-dicarbohydrazide in hydrochloric acid. The structure of the n

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23

M., A. HASSAN, and F. M. FAHMY A. "Synthesis and Structure Determination of 6-Chloro-1,2,4-triazolo[ 4,3-b ]pyrido[2,3-d] and [3,2-d]pyridazines." Journal of Indian Chemical Society Vol. 66, Feb 1989 (1989): 120–21. https://doi.org/10.5281/zenodo.6303568.

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Faculty of Science, Assint University (Qena), Egypt Faculty of Science, Ain Shams University, Egypt <em>Manuscript received 18 April 1988, accepted 12 October 1988</em> 5,8-Dichloropyrido[2,3-<em>d</em>)pyridazine when treated with hydrazine hydrate gave a mixture of 5-chloro-8-hydrazino- and 8-chloro-5-hydrazinopyrido[2,3-<em>d</em>]pyridazines wbich when allowed to react with formic acid gave 6-chloro-1,2,4-triazolo[4,3-<em>b</em>)pyrido- (2,3-<em>d</em>) and [3,2-<em>d</em>]pyridazines.

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24

Rimaz, Mehdi, Jabbar Khalafy, Nader Noroozi Pesyan, and Rolf H. Prager. "A Simple One-Pot, Three Component Synthesis of 3-Arylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-diones and their Sulfur Analogues as Potential Monoamine Oxidase Inhibitors." Australian Journal of Chemistry 63, no. 3 (2010): 507. http://dx.doi.org/10.1071/ch09569.

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Several new 3-arylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-diones and 3-aryl-5-oxo-7-thioxo-7,8-dihydropyrimido[4,5-c]pyridazin-5(6H)-ones have been synthesized by a three-component reaction of barbituric acid or thiobarbituric acid with arylglyoxals in the presence of a catalytic amount of pyridine and hydrazine hydrate at room temperature in water.

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25

Youssef, A. SA, M. I. Marzouk, H. MF Madkour, A. MA El-Soll, and M. A. El-Hashash. "Synthesis of some heterocyclic systems of anticipated biological activities via 6-aryl-4-pyrazol-1-yl-pyridazin-3-one." Canadian Journal of Chemistry 83, no. 3 (2005): 251–59. http://dx.doi.org/10.1139/v05-045.

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6-Aryl-4-pyrazol-1-yl-pyridazin-3-one (1) reacted with a PCl5POCl3 mixture to give the 3-chloropyridazine derivative 3. Reaction of 3 with 2-hydroxybenzoylhydrazide and semicarbazide hydrochloride afforded 4 and 5. Reaction of 1 with ethyl chloroacetate gave 8. Reaction of 8 with hydrazine hydrate yielded the hydrazide 9. The hydrazide 9 condensed with the acetylenic ketones and esters 10a10d and acetylacetone to give the adducts 11a, 11b, 12, 13, and 14. Reacting 1 with formaldehyde and piperidine, morpholine, or piperazine, 3-bromopropanoic acid, acetic anhydride, p-toluenesulphonyl chlori

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26

Barlin, GB, LP Davies, and SJ Ireland. "Imidazo[1,2-b]Pyridazines. XIX. Syntheses and Central Nervous System Activities of Some 6-Arylthio(aryloxy and alkylthio)-3-(acetamidomethyl, benzamidomethyl, methoxy and unsubstituted)-2-arylimidazo[1,2-b]pyridazines." Australian Journal of Chemistry 49, no. 4 (1996): 443. http://dx.doi.org/10.1071/ch9960443.

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Some 6-arylthio( aryloxy and alkylthio )-3-( acetamidomethyl , benzamidomethyl, methoxy and unsubstituted )-2-arylimidazo[1,2-b] pyridazines have been prepared and examined for their ability to displace [3H]diazepam from rat brain membranes. The most active compound was 3-acetamidomethyl-2-(3',4'-methylenedioxyphenyl)-6-phenylthioimidazo[1,2-b] pyridazine with IC50 4.4 nM. The 3-acylaminomethyl-6-(2- and 3-methoxyphenylthio)-2-phenylimidazo[1,2-b] pyridazines proved less active than their 6-phenylthio analogues, and larger substituents at the 2- and 6-positions markedly decreased binding. Sign

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27

Barlin, GB, LP Davies, and MML Ngu. "Imidazo[1,2-b]Pyridazines. VIII. Syntheses and Central Nervous System Activities of Some 6-Benzylamino (and methoxybenzylamino)-3-methoxy-2-phenyl(Substituted phenyl or pyridinyl)imidazo[1,2-b]pyridazines." Australian Journal of Chemistry 42, no. 10 (1989): 1759. http://dx.doi.org/10.1071/ch9891759.

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Syntheses and IC50 values for the displacement of 3H-diazepam from rat brain plasma membrane are reported for a series of 6-benzylamino(and methoxybenzylamino )-3-methoxy-2-phenyl(substituted phenyl and pyridinyl )imidazo[l,2-b]pyridazines (and their 6-anilino and 6-phenethylamino analogues). The results are compared with those reported previously (by us) for the 6-chloro, 6-phenoxy, 6-benzylthio, and 6-benzyloxy compounds. In the imidazo[l,2-b]pyridazine ring system, 6-(o- and m- methoxybenzylamino ) groups were found to be beneficial to binding activity; eight compounds have been prepared wi

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28

M., A. HASSAN, and F. M. FAHMY A. "Synthesis and Structure Determination of 6-Chloro- 1 ,2,4-triazolo[4,3-b]pyrido[2,3-d] and [3,2-d]pyriclazines." Journal of Indian Chemical Society Vol. 66, Feb 1989 (1989): 120–21. https://doi.org/10.5281/zenodo.5995217.

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Faculty of Science, Assiut University(qena), Egypt Faculty of Science, Ain Shams University, Egypt <em>Manuscript received 18 April 1988, accepted 22 October 1988</em> <strong>5,8-Dichloropyrido[2,3-<em>d</em>]pyridazine when treated with hydrazine hydrate gave a mixture of 5-chloro-8-hydrazino- and 8-chloro-5-hydrazinopyrido[2,3-<em>d</em>]pyridazines which when allowed to react<em> </em>with formic add gave 6-chloro-1,2,4-triazolo[4,3-<em>b</em>] pyrido[2,3-<em>d</em>] and [3,2-<em>d</em>]pyridazines</strong>  

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29

Constable, Edwin C., Catherine E. Housecroft, Markus Neuburger, Sébastien Reymann, and Silvia Schaffner. "4-Substituted 3,6-Bis(2-pyridyl)pyridazines: Silver(I) Complexes of 4-Cyano- and 4-(4-Bromophenyl)-3,6-bis(2-pyridyl)pyridazine and Pseudopolymorphs of 1,3,5-Tris{3,6-bis(2-pyridyl)pyridazin-4-yl}benzene." Australian Journal of Chemistry 61, no. 11 (2008): 847. http://dx.doi.org/10.1071/ch08369.

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Metal:ligand complexes are crystallized from reaction mixtures of equimolar amounts of 4-cyano-3,6-bis(2-pyridyl)pyridazine 2 or 4-(4-bromophenyl)-3,6-bis(2-pyridyl)pyridazine 3 and silver(i) triflate. In [Ag2(2)2]2+, the two ligands adopt a head-to-tail arrangement, while a head-to-head motif is confirmed for the solid state structure of [Ag2(3)2]2+. In solution, one ligand environment is observed in each case. Silver(i) reacts with 1,3,5-tris{3,6-bis(2-pyridyl)pyridazin-4-yl}benzene 4 to give highly insoluble powders. The single crystal structures of the pseudopolymorphs (4)·Et2O and 2(4)·2M

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30

Abdelrazek, Fathy M., Ahmed A. Fadda, and Akram N. Elsayed. "ChemInform Abstract: Novel Synthesis of Some New Pyridazine and Pyridazino[4,5-d]pyridazine Derivatives." ChemInform 42, no. 38 (2011): no. http://dx.doi.org/10.1002/chin.201138153.

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31

Ciccolini, Cecilia, Lucia De Crescentini, Fabio Mantellini, Giacomo Mari, Stefania Santeusanio, and Gianfranco Favi. "Construction of Unusual Indole-Based Heterocycles from Tetrahydro-1H-pyridazino[3,4-b]indoles." Molecules 25, no. 18 (2020): 4124. http://dx.doi.org/10.3390/molecules25184124.

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Herein, we report the successful syntheses of scarcely represented indole-based heterocycles which have a structural connection with biologically active natural-like molecules. The selective oxidation of indoline nucleus to indole, hydrolysis of ester and carbamoyl residues followed by decarboxylation with concomitant aromatization of the pyridazine ring starting from tetrahydro-1H-pyridazino[3,4-b]indole derivatives lead to fused indole-pyridazine compounds. On the other hand, non-fused indole-pyrazol-5-one scaffolds are easily prepared by subjecting the same C2,C3-fused indoline tetrahydropy

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32

Barlin, GB, LP Davies, B. Glenn, PW Harrison, and SJ Ireland. "Imidazo[1,2-b]pyridazines. XV. Synthesis and Anxiolytic Activity of Some 3-(Benzamidomethyl and fluorobenzamidomethyl)-6-(fluoro, chloro and methylthio)-2-(4-tolyl and 3,4-methylenedioxyphenyl)imidazo[1,2-b]pyridazines." Australian Journal of Chemistry 47, no. 4 (1994): 609. http://dx.doi.org/10.1071/ch9940609.

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Syntheses are reported for some 3-( benzamido-and fluorobenzamido -methyl)-6-( fluoro , chloro and methylthio )-2(4-methyl-, 4-t-butyl-, 4-cyclohexyl- and 3,4-methylenedioxy-phenyl) imidazo-[1,2-b] pyridazines from the relevant 3-unsubstituted imidazo [1,2-b] pyridazines and the N-( hydroxymethyl ) benzamides. In tests of the ability of these compounds to displace [3H]diazepam from rat brain membrane, 3-(3- or 4-fluorobenzamidomethyl)-2-(3,4-methylenedioxyphenyl)-6-methylthioimidazo[1,2-b]- pyridazine bound most strongly, with IC50 2nM; but in behavioural tests in rats the most active compound

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33

Heinisch, Gottfried, and Wolfgang Holzer. "13C nuclear magnetic resonance spectra of 3,6-disubstituted pyridazines." Canadian Journal of Chemistry 69, no. 6 (1991): 972–77. http://dx.doi.org/10.1139/v91-142.

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The 13C nuclear magnetic resonance spectra of 17 3,6-disubstituted pyridazine derivatives have been systematically analyzed. Chemical shifts and various 13C, 1H coupling constants are reported. Attempts were made to correlate these data with results obtained from semiempirical molecular orbital calculations as well as with substituent electronegativities and Taft's substituent constants σI and σR0. Key words: 3,6-disubstituted pyridazines, 13C NMR spectroscopy, 13C, 1H spin coupling constants.

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34

Daoui, Said, Emine Berrin Cinar, Fouad El Kalai, et al. "Crystal structure and Hirshfeld surface analysis of 4-(4-methylbenzyl)-6-phenylpyridazin-3(2H)-one." Acta Crystallographica Section E Crystallographic Communications 75, no. 9 (2019): 1352–56. http://dx.doi.org/10.1107/s2056989019011551.

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In this paper, we describe the synthesis of a new dihydro-2H-pyridazin-3-one derivative. The molecule, C18H16N2O, is not planar; the benzene and pyridazine rings are twisted with respect to each other, making a dihedral angle of 11.47 (2)°, and the toluene ring is nearly perpendicular to the pyridazine ring, with a dihedral angle of 89.624 (1)°. The molecular conformation is stabilized by weak intramolecular C—H...N contacts. In the crystal, pairs of N—H...O hydrogen bonds link the molecules into inversion dimers with an R 2 2(8) ring motif. The intermolecular interactions were investigated us

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35

Mecadon, Hormi, and Bekington Myrboh. "Potassium Hydroxide Impregnated Alumina (KOH-Alumina) as a Recyclable Catalyst for the Solvent-Free Multicomponent Synthesis of Highly Functionalized Substituted Pyridazines and/or Substituted Pyridazin-3(2H)-ones under Microwave Irradiation." ISRN Organic Chemistry 2011 (April 12, 2011): 1–7. http://dx.doi.org/10.5402/2011/406427.

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The work described herein employs potassium hydroxide impregnated alumina (KOH-alumina) as a mild, efficient, and recyclable catalyst for a one-pot solvent-free and environmentally safer synthesis of 3,4,6-triarylpyridazines and some substituted pyridazines from active methylene carbonyl species, 1,2-dicarbonyls, and hydrazine hydrate by microwave (MW) irradiation. The method offers highly convergent, inexpensive, and functionality-tolerable procedure for rapid access to important pyridazine compounds in good yields.

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36

Degtyarenko, Anna S., та Konstantin V. Domasevitch. "Cadmium(II) iodide and thiocyanate complexes adopted by polycyclic 1,4-bis(pyridazin-4-yl)benzene: interplay of coordination and π–π stacking interactions". Acta Crystallographica Section C Crystal Structure Communications 69, № 3 (2013): 219–24. http://dx.doi.org/10.1107/s0108270113002801.

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New complexes containing the 1,4-bis(pyridazin-4-yl)benzene ligand, namely diaquatetrakis[1,4-bis(pyridazin-4-yl)benzene-κN2]cadmium(II) hexaiodidodicadmate(II), [Cd(C14H10N4)4(H2O)2][Cd2I6], (I), and poly[[μ-1,4-bis(pyridazin-4-yl)benzene-κ2N2:N2′]bis(μ-thiocyanato-κ2N:S)cadmium(II)], [Cd(NCS)2(C14H10N4)]n, (II), demonstrate the adaptability of the coordination geometries towards the demands of slipped π–π stacking interactions between the extended organic ligands. In (I), the discrete cationic [Cd—N = 2.408 (3) and 2.413 (3) Å] and anionic [Cd—I = 2.709 (2)–3.1201 (14) Å] entities are situat

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37

Barlin, Gordon B., Les P. Davies, Stephen J. Ireland, and Maria M. L. Ngu-Schwemlein. "Imidazo[1,2-b]pyridazines. XXII. Syntheses of Some 2-Aryl-3-methoxy-6-(pyridinylmethylthio and pyridinylmethylamino)imidazo[1,2-b]pyridazines and Their Interaction with Central and Mitochondrial (Peripheral-Type) Benzodiazepine Receptors." Australian Journal of Chemistry 50, no. 2 (1997): 91. http://dx.doi.org/10.1071/c96136.

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2-Aryl-3-methoxy-6-(pyridinylmethylthio and pyridinylmethylamino)imidazo[1,2-b]pyridazines have been prepared and examined as ligands for benzodiazepine receptors. Most were highly effective in displacing [3H]diazepam from central benzodiazepine receptors present in rat brain membranes but showed little capacity for its displacement from mitochondrial (peripheral-type) benzodiazepine receptors present in rat kidney membranes. For example, 3-methoxy-2-(3′,4′-methylenedioxyphenyl)-6-(pyridin-2′′-ylmethylthio)imidazo[1,2-b]pyridazine had an IC50 value of 1 · 7 nM for central receptors but gave on

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38

El Kalai, Fouad, Cemile Baydere, Said Daoui, et al. "Crystal structure and Hirshfeld surface analysis of ethyl 2-[5-(3-chlorobenzyl)-6-oxo-3-phenyl-1,6-dihydropyridazin-1-yl]acetate." Acta Crystallographica Section E Crystallographic Communications 75, no. 6 (2019): 892–95. http://dx.doi.org/10.1107/s2056989019007424.

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The title pyridazinone derivative, C21H19ClN2O3, is not planar. The unsubstituted phenyl ring and the pyridazine ring are inclined to each other, making a dihedral angle of 17.41 (13)° whereas the Cl-substituted phenyl ring is nearly orthogonal to the pyridazine ring [88.19 (13)°]. In the crystal, C—H...O hydrogen bonds generate dimers with R 2 2(10) and R 2 2(24) ring motifs which are linked by C—H...O interactions, forming chains extending parallel to the c-axis direction. The intermolecular interactions were investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots

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39

Norman, Rebecca E., Michael V. Perkins, Andris J. Liepa, and Craig L. Francis. "N,N-Dialkyl-N′-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part X. The First Pyrazolo[1,5-b][1,2,4,6]thiatriazine Derivatives and their Unusual Reactions with Acylating Agents." Australian Journal of Chemistry 66, no. 11 (2013): 1323. http://dx.doi.org/10.1071/ch13282.

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N,N-dialkyl-N′-chlorosulfonyl chloroformamidines 1 underwent a regioselective reaction with 3-aminopyrazoles 2 to produce pyrazolo[1,5-b][1,2,4,6]thiatriazines 3, representatives of a new ring system. Attempted N-acylation of compounds 3 with acetic anhydride (or chloride) and benzoyl chloride in pyridine, only afforded 5-(pyridin-4-yl)-pyrazolo[1,5-b][1,2,4,6]thiatriazine derivatives 11. The analogous reaction with pyridazine led to the corresponding pyridazin-4-yl derivative.

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40

Chen, Liqin, Laurence K. Thompson, and John N. Bridson. "Coordination chemistry of thioether–pyridazine macrocycles. I. Synthetic, structural, and spectroscopic studies of Cu(II) and Cu(I) complexes of novel thioether–pyridazine macrocycles that contain two or three pyridazine subunits." Canadian Journal of Chemistry 70, no. 7 (1992): 1886–96. http://dx.doi.org/10.1139/v92-236.

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The preparations of thioether–pyridazine macrocycles containing three (L1) and two (L2) pyridazine subunits and their copper complexes are described. The ligands are characterized by 1H nuclear magnetic resonance and mass spectrometry and in one case by X-ray crystallography, and the complexes by infrared, electronic, and electron spin resonance (esr) spectra and in some cases by X-ray crystallography. The complex [Cu3(L1)2Cl6]•2CHCl3 (1) crystallized in the triclinic system, space group [Formula: see text] with a = 13.661(2) Å, b = 14.174(3) Å, c = 9.412(2) Å, α = 101.08(2)°, β = 96.94(2)°, γ

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41

Chen, Liqin, Laurence K. Thompson, and John N. Bridson. "Coordination chemistry of thioether–pyridazine macrocycles. III. Synthetic, structural, and spectroscopic studies of Cu(II), Cu(II)Cu(I), and Cu(I) complexes of a hexathiapyridazinophane macrocyclic ligand." Canadian Journal of Chemistry 71, no. 7 (1993): 1086–93. http://dx.doi.org/10.1139/v93-144.

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The preparation and properties of the thioether–pyridazine macrocycle (L4; C16H20S6N4) containing two pyridazine subunits, and its Cu(II), Cu(II)Cu(I), and Cu(I) complexes are described. The ligand is characterized by 1H nuclear magnetic resonance and mass spectrometry, and the complexes by infrared, eleetronic spectra, and magnetism, and in some cases by X-ray crystallography. The complex [Cu2(L4)Cl4]x, (1) crystallized in the triclinic system, space group [Formula: see text] with a = 8.6204(8) Å, b = 9.850(1) Å, c = 8.348(1) Å, α = 111.46(1)°, β = 102.50(1)°, γ = 71.818(9)°, V = 622.6(1) Å3,

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42

Aziz, Suzan Ibrahim, Hany Fakhry Anwar, Morsy Ahmed El-Apasery, and Mohamed Hilmy Elnagdi. "Studies with pyridazines and condensed pyridazines: Routes for synthesis of 3-amino-5-aryl-2,5-dihydro-pyridazine, 10aH-pyridazino[1,6-a]quinazoline and thieno[3,4-d]pyridazinone." Journal of Heterocyclic Chemistry 44, no. 4 (2007): 877–81. http://dx.doi.org/10.1002/jhet.5570440421.

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43

El-Din, Harb. "Synthesis and reactions of 4-(p-methoxybenzyl)-6-[5,6,7,8-tetrahydro-2-naphthyl]-pyridazin-3(2H-one." Journal of the Serbian Chemical Society 64, no. 11 (1999): 663–72. http://dx.doi.org/10.2298/jsc9911663e.

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The condensation of 4-(p-methoxybenzyl)-6-[5,6,7,8-tetrahydro-2-naphthyl]- pyridazin-3(2H)-one (3), prepared by the reaction of 6-[5,6,7,8-tetrahydro-2-naphthyl]-4,5-dihydropyridazin-3(2H)-one (1) and anisaldehyde, with dimethyl sulphate, formal-dehyde and acrylonitrile, and also the formation of the Mannich base, proceeded smoothly at the 2-position to give compounds 4,5,6,7, respectively. 4-p-Methoxybenzyl-3-chloro-6-[5,6,7,8-tetrahydro-2-naphthyl]-pyridazine (9) was prepared in law yield by the action of phosphorus oxychloride on 3. The reaction of 9 with benzylamine, aniline and piperidine

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44

Deeb, Ali, Abdel Naby Essawy, Fathy Yasine, and Rida Fikry. "Pyridazine Derivatives and Related Compounds, Part 3 [1] Some Reactions with 4-Cyano-3(2H)-pyridazinethione." Zeitschrift für Naturforschung B 46, no. 6 (1991): 835. http://dx.doi.org/10.1515/znb-1991-0620.

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The reaction of 5-amino-3,4-diphenylthieno[2,3-c]pyridazine-6-carboxamide 2 with formamide, acetic anhydride and carbon disulphide yielded pyrimido[4′,5′ :4,5]thieno[2,3-c]-pyridazin-4-one derivatives. Pyrimido[4,5-c]pyridazinethione and dithione derivatives were obtained by cyclocondensation of 3-amino-5,6-diphenylpyridazine-4-carbonitrile (8) with phenyl isothiocyanate and carbon disulphide, respectively. Tetrahydropyridazino[3,4-b]-quinoline (11) was prepared by reaction of 8 with cyclohexanone in presence of zinc chloride.

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45

Barlin, Gordon B., Les P. Davies, and Peter W. Harrison. "Imidazo[1,2-b]pyridazines. XXI. Syntheses of some 3-Acylaminomethyl-6-(chloro and iodo)- 2-(substituted phenyl)-imidazo[1,2-b]pyridazines and -imidazo[1,2-a]pyridines and their Interaction with Central and Mitochondrial Benzodiazepine." Australian Journal of Chemistry 50, no. 1 (1997): 61. http://dx.doi.org/10.1071/c96130.

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A series of 3-acylaminomethyl-6-(chloro, iodo and methyl)-2-(phenyl, 4′-t-butylphenyl, 4′-cyclohexyl- phenyl, biphenyl-4′-yl, 4′-chlorophenyl and 4′-iodophenyl)imidazo[1,2-b]pyridazines and imidazo[1,2- a]pyridines has been prepared and examined for interaction with central and mitochondrial (peripheral- type) benzodiazepine receptors. The imidazo[1,2-b]pyridazines were generally more selective for the mitochondrial receptors than the corresponding imidazo[1,2-a]pyridines. Of these compounds, 3- acetamidomethyl-2-(biphenyl-4′-yl)-6-chloroimidazo[1,2-b]pyridazine (9) proved to be the most selec

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46

Barlin, GB, LP Davies, RA Davis, and PW Harrison. "Imidazo[1,2-b]pyridazines. XVII. Synthesis and Central Nervous System Activity of Some 6-(Alkylthio and chloro)-3-(methoxy, unsubstituted and benzamidomethyl)-2-arylimidazo[1,2-b]pyridazines Containing Methoxy, Methylenedioxy and Methyl Substituents." Australian Journal of Chemistry 47, no. 11 (1994): 2001. http://dx.doi.org/10.1071/ch9942001.

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Syntheses are reported for 6-( methylthio, ethylthio, propylthio, substituted benzylthio and chloro )-3-( methoxy, unsubstituted and benzamidomethyl )-2-arylimidazo[1,2-b] pyridazines containing methoxy, methylenedioxy and methyl groups attached to phenyl substituents . In tests of the ability of these compounds to displace [3H]diazepam from rat brain membranes, 3-methoxy-6-(3′,4′-methylenedioxybenzylthio)-2- (3′,4′-methylenedioxyphenyl) imidazo [1,2-b] pyridazine (IC50 1 nM) bound most strongly; methylenedioxy groups were beneficial to activity whereas polymethoxy or dimethyl substituents wer

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47

Okamura, Hidenori, Giang Hoang Trinh, Zhuoxin Dong, Yoshiaki Masaki, Kohji Seio, and Fumi Nagatsugi. "Selective and stable base pairing by alkynylated nucleosides featuring a spatially-separated recognition interface." Nucleic Acids Research 50, no. 6 (2022): 3042–55. http://dx.doi.org/10.1093/nar/gkac140.

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Abstract Unnatural base pairs (UBPs) which exhibit a selectivity against pairing with canonical nucleobases provide a powerful tool for the development of nucleic acid-based technologies. As an alternative strategy to the conventional UBP designs, which involve utility of different recognition modes at the Watson–Crick interface, we now report that the exclusive base pairing can be achieved through the spatial separation of recognition units. The design concept was demonstrated with the alkynylated purine (NPu, OPu) and pyridazine (NPz, OPz) nucleosides endowed with nucleobase-like 2-aminopyri

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48

Daoui, Said, Cemile Baydere, Fouad El Kalai, et al. "Crystal structure, Hirshfeld surface analysis and DFT studies of 2-[5-(4-methylbenzyl)-6-oxo-3-phenyl-1,6-dihydropyridazin-1-yl]acetic acid." Acta Crystallographica Section E Crystallographic Communications 75, no. 12 (2019): 1925–29. http://dx.doi.org/10.1107/s2056989019015317.

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The title pyridazinone derivative, C20H18N2O3, is not planar. The phenyl ring and the pyridazine ring are inclined to each other by 10.55 (12)°, whereas the 4-methylbenzyl ring is nearly orthogonal to the pyridazine ring, with a dihedral angle of 72.97 (10)°. In the crystal, molecules are linked by pairs of O—H...O hydrogen bonds, forming inversion dimers with an R 2 2(14) ring motif. The dimers are linked by C—H...O hydrogen bonds, generating ribbons propagating along the c-axis direction. The intermolecular interactions were additionally investigated using Hirshfeld surface analysis and two-

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49

Mojahidul, Islam, and Arora Sethi Vandana. "Synthesis and antiviral activity of 3-substituted phenyl-6-substituted phenyl (1,2,4) triazolo (4,3-b) pyridazin." Pharmaceutical and Chemical Journal 4, no. 6 (2017): 28–33. https://doi.org/10.5281/zenodo.13885851.

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A series of 3-substituted phenyl -6-substituted phenyl (1,2,4) triazolo (4,3-b) pyridazine has been synthesized. An appropriate aromatic hydrocarbon reacts with succinic anhydride in presence of AlCl<sub>3   </sub>to yield β-aroyl propionic acid. The corresponding acid was cyclised with hydrazine hydrate to give 6-(substituted aryl)-2, 3, 4, 5-tetrahydro-3-pyridazinone, which was heated on steam bath with phosphorous oxy chloride to yield 3-chloro 6-substituted phenyl pyradazine. This intermediate after reaction with hydrazine hydrate was converted into 3-hydrazino-6-substituted

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50

Degtyarenko, Anna S., та Konstantin V. Domasevitch. "Anion...π interactions in copper(I) chloride and bromide coordination polymers bearing 1,4-bis(pyridazin-4-yl)benzene ligands". Acta Crystallographica Section C Structural Chemistry 70, № 2 (2014): 173–77. http://dx.doi.org/10.1107/s2053229613034840.

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In poly[[μ4-1,4-bis(pyridazin-4-yl)benzene-1:2:3:4κ4N1:N2:N1′:N2′]di-μ2-chlorido-dicopper(I)], [Cu2Cl2(C14H10N4)]n, (I), and its isomorphous bromide analogue, [Cu2Br2(C14H10N4)]n, (II), the organic ligand is situated across a centre of inversion. The CuIcations adopt a distorted tetrahedral [CuN2X2] [X= Cl in (I) or Br in (II)] environment [Cu—N = 2.0183 (14)–2.0936 (14) Å; Cu—Cl = 2.2686 (6) and 2.4241 (5) Å; Cu—Br = 2.4002 (6) and 2.5284 (5) Å] and the primary coordination motif consists of cuprohalogenide chains accommodating μ-pyridazine groups. The organic ligands are tetradentate and lin

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