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Journal articles on the topic 'Pyridazines'

Author: Grafiati

Published: 4 June 2021

Last updated: 25 July 2025

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1

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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2

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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3

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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4

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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5

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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6

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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7

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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8

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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9

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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10

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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11

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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12

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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13

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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14

Barlin, GB, and SJ Ireland. "Imidazo[1,2-B]pyridazines. II. 6-Alkylthio and 6-Arylthio-3-methoxy-2-phenylimidazo[1,2-b]pyridazines." Australian Journal of Chemistry 40, no. 8 (1987): 1491. http://dx.doi.org/10.1071/ch9871491.

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A series of 6-alkylthio- and 6-arylthio-3-methoxy-2-phenylimidazo[l,2- b]pyridazines has been prepared from 6-alkylthio-and 6-arylthio-pyridazin-3-amines through the corresponding 6-alkylthio-and 6-arylthio-2-phenylimidazo[l,2-b] pyridazin-3(5H)-ones.

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15

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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16

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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17

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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18

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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19

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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20

Zanatta, Nilo, Mário A. Marangoni, Paulo A. Moraes, Adriano F. Camargo, Helio G. Bonacorso, and Marcos A. P. Martins. "Synthesis of a Novel 1,4-Dicarbonyl Scaffold – Ethyl 3-Formyl-4,5-dihydrofuran-2-carboxylate – and Its Application to the Synthesis of Pyridazines." Synthesis 52, no. 17 (2020): 2528–34. http://dx.doi.org/10.1055/s-0039-1690886.

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The 1,4-dicarbonyl scaffold ethyl 3-formyl-4,5-dihydrofuran-2-carboxylate was obtained through the rearrangement of the parent ethyl 2-(4,5-dihydrofuran-3-yl)-2-oxoacetate and applied to the synthesis of a series of 7-alkoxy-2,3-dihydrofuro[2,3-d]pyridazines. Twelve pyridazines were obtained in yields of up to 70%.

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21

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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22

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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23

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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24

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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25

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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26

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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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

Barlin, GB, LP Davies, SJ Ireland, MML Ngu, and JK Zhang. "Imidazo[1,2-b]pyridazines. X. Syntheses and Central Nervous System Activities of Some 3-(Acetamido, benzamido, substituted benzamido or dimethylamino)methyl-2-(phenyl or substituted phenyl)-6-(halogeno, alkylthio, alkoxy, phenylthio, phenoxy, benzylthio or benzyloxy)imidazo[1,2-b]pyridazines." Australian Journal of Chemistry 45, no. 4 (1992): 731. http://dx.doi.org/10.1071/ch9920731.

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Syntheses of some 3-( acetamido, benzamido , substituted benzamido or dimethylamino)methyl-2-(phenyl or substituted phenyl)-6( halogeno, alkylthio, alkoxy, phenylthio, phenoxy , benzylthio or benzyloxy ) imidazo [1,2-b] pyridazines from the 3-unsubstituted analogues are described. The IC50 values (or percentage displacements) are reported and discussed for the displacement of [3H]diazepam from rat brain membrane by each of these compounds. .The 3-benzamidomethyl compounds were generally the most active; of these, 3-benzamidomethyl-2-(3',4'-methylenedioxyphenyl)-6-methylthioimido[1,2-b] pyridaz

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29

Barlin, GB, LP Davies, SJ Ireland, and JK Zhang. "Imidazo[1,2-b]pyridazines. XIII. Syntheses and Central Nervous System Activities of Some 2-Benzyl(phenethyl, biphenyl-4'-yl, 6'-methylnaphthalen-2'-yl, t-Butyl and cyclohexyl)-3-methoxy(acylaminomethyl and dimethylaminomethyl)-6-(variously substituted)imidazo[1,2-b]pyridazines." Australian Journal of Chemistry 45, no. 8 (1992): 1281. http://dx.doi.org/10.1071/ch9921281.

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6-(Variously substituted)-3-methoxy(unsubstituted, dimethylaminomethyl, acetamidomethyl and benzamidomethy1)-2-benzyl(phenethyl, biphenyl-4'-yl, 6'-methylnaphthalen-2'-yl, t-butyl and cyclohexyl)imidazo[1,2-b] pyridazines have been prepared and examined for activity in the central nervous system. Of these, 2-benzyl-3-methoxy-6-(3'-methoxybenzylamino) imidazo[1,2-b]pyridazine (IC50 88nM) bound most strongly to rat brain membrane. In general, the order of activity for groups at the 2-position was Ph > PhCH2 > PhCH2CH2 > C6H4Ph-p, 6'-methylnaphthalen-2'-yl, c-C6H11 or But.

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30

Barlin, GB, LP Davies, and MML Ngu. "Imidazo[1,2-B]Pyridazines. III. Syntheses and Central Nervous-System Activities of Some 6-Chloro-3-methoxy (and ethoxy)-2-aryl (and heteroaryl)imidazo[1,2-B]pyridazines." Australian Journal of Chemistry 41, no. 8 (1988): 1149. http://dx.doi.org/10.1071/ch9881149.

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The synthesis of a series of 6-chloro-3-methoxy(and ethoxy )-2- phenyl[and (variously substituted phenyl), thienyl, and naphthalenyl ] imidazo [1,2-b] pyridazines and a 6-fluoro analogue are reported. These compounds were tested for their ability to displace [3H]diazepam bound to washed rat brain plasma membranes. Under standard assay conditions (see Experimental) and in the presence of 100 μM γ- aminobutyric acid, 6-chloro-3-methoxy-2-(p-tolyl ) imidazo [1,2- b] pyridazine was the most active compound with an IC50 value of 148 nM (cf. diazepam, with IC50 of 4.2 nM).

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31

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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32

Barlin, GB, LP Davies, and MML Ngu. "Imidazo[1,2-b]pyridazines. IV. Syntheses and Central Nervous System Activities of Some 3-Methoxy-6-phenoxy(Substituted Phenoxy and Naphthyloxy)-2-phenylimidazo[1,2-b]pyridazines." Australian Journal of Chemistry 41, no. 11 (1988): 1735. http://dx.doi.org/10.1071/ch9881735.

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Syntheses are reported for some 3-methoxy-6-phenoxy(substituted phenoxy and naphthyloxy )-2-phenylimidazo[1,2-b] pyridazines; they were made in order to study their possible pharmacological activity in the mammalian central and peripheral nervous system. In initial biological screens to detect compounds with potential activity at receptors for the benzodiazepine class of drugs, the most active compounds were 3-methoxy-6-(2′-methylthiophenoxy)- and 6-(2′-dimethylaminophenoxy )-3-methoxy-2-phenylimidazo[1,2-b] pyridazine. Their respective IC50 values for displacement of 3H-diazepam (IC50 for unl

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33

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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34

Barlin, GB, LP Davies, and MML Ngu. "Imidazo[1,2-b]pyridazines. VII. Syntheses and Central Nervous System Activities of Some 3-Alkoxy-6-benzyloxy (and methoxy-benzyloxy)-2-phenyl(substituted phenyl or pyridinyl)imidazo[1,2-b]pyridazines." Australian Journal of Chemistry 42, no. 10 (1989): 1749. http://dx.doi.org/10.1071/ch9891749.

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A series of 15 3-alkoxy-6-benzyloxy( methoxybenzyloxy )-2-phenyl( sbstitted phenyl and pyridinyl )imidazo[l,2-b]pyridazines has been prepared and each compound tested for its ability to displace 3H-diazepam from rat brain plasma membranes. The results have been compared with data previously obtained for other derivatives of this ring system. Compounds containing 6(o- or m- methoxybenzyloxy ) groups were more effective in the displacement of 3H-diazepam than those with the 6-benzyloxy group; and the most active compound was 2-(p- fluorophenyl )-3-methoxy-6-(m- methoxybenzyloxy )imidazo[l,2 b]py

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35

Koçak, Ramazan, та Arif Daştan. "Synthesis of dibenzosuberenone-based novel polycyclic π-conjugated dihydropyridazines, pyridazines and pyrroles". Beilstein Journal of Organic Chemistry 17 (15 березня 2021): 719–29. http://dx.doi.org/10.3762/bjoc.17.61.

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The synthesis of novel polycyclic π-conjugated dihydropyridazines, pyridazines, and pyrroles was studied. Dihydropyridazine dyes were synthesized by inverse electron-demand Diels–Alder cycloaddition reactions between a dibenzosuberenone and tetrazines that bear various substituents. The pyridazines were synthesized in high yields by oxidation of dihydropyridazine-appended dibenzosuberenones with PIFA or NO. p-Quinone derivatives of pyridazines were also obtained by H-shift isomerization following the inverse electron-demand Diels–Alder reaction of tetrazines with p-quinone dibenzosuberenone. T

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36

Barlin, GB, LP Davies, SJ Ireland, and MML Ngu. "Imidazo[1,2-b]Pyridazines. V. Syntheses and Central Nervous Activities of Some 3-Alkoxy-6-benzylthio(substituted benzylthio and Other phenylalkylthio)-2-phenyl(and substituted phenyl)imidazo[1,2-b]pyridazines." Australian Journal of Chemistry 42, no. 7 (1989): 1133. http://dx.doi.org/10.1071/ch9891133.

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Syntheses are reported for a number of 3-alkoxy-6-benzylthio(substituted benzylthio and other phenylalkylthio )-2-phenyl(and substituted phenyl)imidazo[l,2-b]pyridazines. These compounds were then examined for their ability to displace 3H-diazepam from rat brain membranes. In preliminary tests, in the presence of 100 �m γ- aminobutyric acid (GABA) and under standard assay conditions (see Experimental), 6-benzylthio-3-methoxy-2-phenylimidazo[l,2- b]pyridazine gave an lC50 value of 25nM (IC50 for unlabelled diazepam is 4.3 nM ); its 6-(m- aminophenyl ), 6-(p- aminophenyl ) and 6-(m- nitrophenyl

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37

Heinisch, Gottfried, and Gerhard Lötsch. "Pyridazines XXIV." Tetrahedron 41, no. 7 (1985): 1199–205. http://dx.doi.org/10.1016/s0040-4020(01)96521-4.

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38

Alegbejo Price, Temitayo Omowumi, Flavio da Silva Emery, and Wim Dehaen. "Synthetic Pathways to Pyrido[3,4-c]pyridazines and Their Polycyclic Derivatives." Organics 3, no. 4 (2022): 430–45. http://dx.doi.org/10.3390/org3040028.

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Pyrido[3,4-c]pyridazines are nitrogen-containing scaffolds that have been described as being promising in medicinal chemistry, but they are rather rare chemicals. In this review article, the literature on synthetic pathways towards pyrido[3,4-c]pyridazines is listed exhaustively, first with the bicyclic systems themselves that are obtained starting either from pyridines, pyridazines or other heterocycles. Then, the reports on the related tricyclic derivatives are discussed, again according to the source heterocycle, and finally we mention some examples on polycyclic systems.

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39

Al-Zaydi, Khadijah Mohamed, and Ebtisam Abdel Aziz Hafez. "1,3-Dipolar Cycloadditions of Some Nitrilimines and Nitrile Oxides to 3-N,N-Dimethylamino-1 -oxopropene Derivatives." Journal of Chemical Research 23, no. 6 (1999): 360–61. http://dx.doi.org/10.1177/174751989902300608.

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An efficient synthesis of some novel pyrazoles 8a-j, 13a-e, 18a,b, isoxazoles 26a-g, pyrazolo[3,4- d]pyridazines 9a-d and isoxazolo[3,4- d]pyridazines 27a-d via 1,3-dipolar cycloaddition reactions is reported.

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40

Buckland, SJ, B. Halton, and B. Stanovnik. "Studies in the Cycloproparene Series: Approaches to Cyclopropaheteroarenes." Australian Journal of Chemistry 40, no. 12 (1987): 2037. http://dx.doi.org/10.1071/ch9872037.

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Photolysis of the pyrazolopyridazines (3) results in the loss of nitrogen. The resultant diradicals (5) do not close to the cyclopropa [d]pyridazines (4) but undergo 1,4-hydrogen transfer to afford the 8-(2'-propenyl)pyridazines (6) instead. In the presence of trapping agents diradicals (5)give ethers (7) with methanol, epoxycyclohepta [d]pyridazines (8) with furan, and the 1,4- and 1,2-addition products (16) and (17) respectively, with butadiene. The formation of (8) and (16)provides the first examples of 1,4-addition of a 1,3-diradical to a diene.

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41

Domasevitch, Konstantin V., Pavlo V. Solntsev, and Joachim Sieler. "Cadmium nitrate coordination polymers with substituted pyridazino[4,5-d]pyridazines." Acta Crystallographica Section C Crystal Structure Communications 62, no. 2 (2006): m70—m73. http://dx.doi.org/10.1107/s0108270106001181.

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42

Deeb, Ali, Ahmed Hataba, Wafaa El‐Eraky, and Hend Abdel-Naby. "PYRIDAZINE AND ITS RELATED COMPOUNDS, SYNTHESIS OF SOME NOVEL CONDENSED PYRIDAZINES." Bulletin of Faculty of Science, Zagazig University 2017, no. 2017 (2017): 367–78. http://dx.doi.org/10.21608/bfszu.2017.31061.

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43

Konečný, Václav, Štefan Kováč, and Štefan Varkonda. "Synthesis, spectral properties, and pesticidal activity of 4-amino(alkylamino, dialkylamino)-5-chloro-2-substituted-3-oxo-2H-pyridazines and 5-amino(alkylamino, dialkylamino)-4-chloro-2-substituted-3-oxo-2H-pyridazines." Collection of Czechoslovak Chemical Communications 50, no. 2 (1985): 492–502. http://dx.doi.org/10.1135/cccc19850492.

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4-Amino(alkylamino)-5-chloro-2-substituted-3-oxo-2H-pyridazines and 5-amino(alkylamino, dialkylamino)-4-chloro-2-substituted-3-oxo-2H-pyridazines have been prepared by nucleophilic substitution reactions of 4,5-dichloro-2-substituted-3-oxo-2H-pyridazines with amines in aprotic solvent. Structure of the compounds prepared has been proved by IR and UV spectra. Fungicidal and herbicidal activity of the compounds prepared have been tested. None of the compounds prepared exceeds the standard Vitavax in the fungicidal activity tests. Compounds VIII and XII show equal or better activity on the Hill r

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44

Mohamed Al-Mousawi, Saleh, Moustafa Sherief Moustafa, Ismail Abdelshafy Abdelhamid, and Mohamed Hilmy Elnagdi. "Optimizing Scale Up Yield to Pyridazines and Fused Pyridazines." Current Organic Chemistry 15, no. 19 (2011): 3503–13. http://dx.doi.org/10.2174/138527211797374760.

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45

Komshina, Ljudmila A., Valentina V. Маrtazova, Mikhail K. Korsakov, Irina K. Proskurina, Аlexandr D. Коtov, and Еlena B. Karavaeva. "Synthesis of sulfonamide derivatives containing the structural fragment of pyrazol-1-yl-pyridazine." Butlerov Communications 64, no. 10 (2020): 22–27. http://dx.doi.org/10.37952/roi-jbc-01/20-64-10-22.

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Sulfonamide derivatives of heterocyclic compounds are promising targets for the search for new substances with specific biological activity. They are widely used as inhibitors of human carbonic anhydrases involved in the implementation of various biochemical processes. The presence of several heterocyclic systems in the structure of sulfonamides significantly increases the ability to bind to active sites of carbonic anhydrases and inhibit their activity. Therefore, the development of approaches to the preparation of sulfonamides of polynuclear heterocyclic compounds is of great scientific inte

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46

Haider, Norbert. "Inverse-electron-demand diels-alder reactions of condensed pyridazines, part 1. Synthesis of phthalazine derivatives from pyridazino[4,5-d]pyridazines." Tetrahedron 47, no. 24 (1991): 3959–68. http://dx.doi.org/10.1016/s0040-4020(01)86436-x.

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47

Ivan, Beatrice-Cristina, Stefania-Felicia Barbuceanu, Camelia Mia Hotnog, et al. "Synthesis, Characterization and Cytotoxic Evaluation of New Pyrrolo[1,2-b]pyridazines Obtained via Mesoionic Oxazolo-Pyridazinones." International Journal of Molecular Sciences 24, no. 14 (2023): 11642. http://dx.doi.org/10.3390/ijms241411642.

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New pyrrolo[1,2-b]pyridazines were synthesized by 3 + 2 cycloaddition reaction between mesoionic oxazolo-pyridazinones and methyl/ethyl propiolate. The mesoionic compounds were generated in situ by action of acetic anhydride on 3(2H)pyridazinone acids obtained from corresponding esters by alkaline hydrolysis followed by acidification. The structures of the compounds were confirmed by elemental analyses and IR, 1H-NMR, 13C-NMR, and X-ray diffraction data. The regioselectivity of cycloaddition was evidenced by NMR spectroscopy and confirmed by X-ray analysis. The compounds were evaluated for the

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48

Barlin, GB, LP Davies, SJ Ireland, and MML Ngu. "Imidazo[1,2-b]Pyridazines. VI. Syntheses and Central Nervous System Activities of Some 6-(Alkoxy- and Methylthio-phenoxy and Methoxybenzylthio)-3-methoxy-2-phenyl(substituted phenyl and pyridinyl)Imidazo[1,2-b]pyridazines." Australian Journal of Chemistry 42, no. 10 (1989): 1735. http://dx.doi.org/10.1071/ch9891735.

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Series of 6-( alkoxy - and methylthio-phenoxy )-2-phenyl(substituted phenyl and pyridiny1)imidazo[l,2-b]pyridazines and 3-methoxy-6-( methoxybenzylthio )-2-phenyl(substituted phenyl and pyridinyl ) imidazo[l,2-b]pyridazines have been prepared and subsequently tested for their ability to inhibit GABA-stimulated 3H-diazepam binding to rat brain plasma membranes. The 6( alkoxy- and methylthio-phenoxy ) and 6-( methoxybenzylthio) compounds were much more effective in the displacement studies than the parent 6-phenoxy or 6-benzylthio compounds respectively. 3-Methoxy-6-(2′-methoxyphenoxy)-2-phenyli

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49

Barlin, GB, LP Davies, SJ Ireland, MML Ngu, and JK Zhang. "Imidazo[1,2-b]pyridazines. XII. Syntheses and Central Nervous System Activities of Some Substituted Imidazo[1,2-b]pyridazines and Related Imidazo[1,2-a]pyridines, Imidazo[1,2-a]pyrimidines and Imidazo[1,2-a]pyrazines." Australian Journal of Chemistry 45, no. 5 (1992): 877. http://dx.doi.org/10.1071/ch9920877.

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Syntheses are reported for some 6-chloro(alkoxy,alkylthio and pheny1thio)-3-benzamidomethyl-(acetamidomethyl and methoxy)-2-arylimidazo[1,2-apyridines and some corresponding imidazo- [1,2- b]pyridazines, imidazo[1,2-a[pyrimidines and imidazo[l,2-a]pyrazines. IC50 values (or percentage displacement) are reported and discussed for the displacement of [3H]diazepam from rat brain membrane by each of these compounds. The imidazo[l,2-a[pyridines were generally slightly less potent than the imidazo[l,2- b]pyridazines but considerably more potent than the corresponding imidazo[1,2-a]pyrimidines or imi

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50

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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