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Journal articles on the topic '6-dihydro-1'

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Published: 3 June 2025

Last updated: 31 July 2025

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1

Collins, David J., Timothy C. Hughes, and Wynona M. Johnson. "Dihydro-1,2,4-triazin-6(1H)-ones. II Synthesis of Several Methylated 3-Phenyl- 4,5-dihydro-1,2,4-triazin-6(1H)-ones." Australian Journal of Chemistry 52, no. 5 (1999): 379. http://dx.doi.org/10.1071/ch99012.

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Novel syntheses of 4,5-dihydro-1,2,4-triazin-6(1H)-ones were developed by use of imidoyl chlorides. The overall yield of 4,5-dihydro-1,2,4-triazin-6(1H)-ones prepared from amino acid imidates and hydrazines was improved by the development of a much more efficient synthesis of the imidates. The new 1,2-, 1,4- and 5,5-dimethyl dihydro-1,2,4-triazin-6(1H)-ones have been synthesized by cyclocondensation/cycloaddition pathways. Base-catalysed methylation of 3-phenyl-4,5-dihydro-1,2,4-triazin-6(1H)-one (15) gave the 1- methylated derivative (8); under similar conditions 2-methyl-3-phenyl-2,5-dihydro

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2

Dhaval, Hingrajia, Thanki Pragna, and Modha Jayesh. "Synthesis and Characterization of some Benzylidinehydrazinyl Derivatives of Newer Pyrimidine-5-Carbonitrile Moiety." International Letters of Chemistry, Physics and Astronomy 39 (October 2014): 28–34. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.39.28.

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Condensation of 2-hydrazinyl-1,6-dihydro-1-methyl-6-oxo-4-isobutylpyrimidine-5-carbonitrile (3) with different aromatic aldehyde gave the corresponding 2-(Benzylidinehydrazinyl)-1,6-dihydro-6-oxo-4-isobutylpyrimidine-5-carbonitrile (4). The reaction between 1,6-dihydro-1-methyl-2-(methylthio)-6-oxo-4-isobutylpyrimidine-5-carbonitrile (2) with hydrazine hydrate furnished (3). The condensation of 1,2,3,4-tetrahydro-4-oxo-6-isobutyl-2-thioxopyrimidine-5-carbonitrile (1) with methyl iodide yielded 2. Finally the products were characterized by 1H NMR, Mass and IR Spectra.

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3

Dhaval, Hingrajia, Thanki Pragna, and Modha Jayesh. "Synthesis and Characterization of some Benzylidinehydrazinyl Derivatives of Newer Pyrimidine-5-Carbonitrile Moiety." International Letters of Chemistry, Physics and Astronomy 39 (October 2, 2014): 28–34. http://dx.doi.org/10.56431/p-sa74y0.

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Condensation of 2-hydrazinyl-1,6-dihydro-1-methyl-6-oxo-4-isobutylpyrimidine-5-carbonitrile (3) with different aromatic aldehyde gave the corresponding 2-(Benzylidinehydrazinyl)-1,6-dihydro-6-oxo-4-isobutylpyrimidine-5-carbonitrile (4). The reaction between 1,6-dihydro-1-methyl-2-(methylthio)-6-oxo-4-isobutylpyrimidine-5-carbonitrile (2) with hydrazine hydrate furnished (3). The condensation of 1,2,3,4-tetrahydro-4-oxo-6-isobutyl-2-thioxopyrimidine-5-carbonitrile (1) with methyl iodide yielded 2. Finally the products were characterized by 1H NMR, Mass and IR Spectra.

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4

Karaburun, Ahmet Cagri, Nalan Gundogdu-Karaburun, Leyla Yurttas, Ismail Kayagil, and Seref Demirayak. "Synthesis and Anticancer Activity of Some 1H-inden-1-one Substituted (Heteroaryl)Acetamide Derivatives." Letters in Drug Design & Discovery 16, no. 2 (2018): 111–18. http://dx.doi.org/10.2174/1570180815666180606081042.

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Background: The synthesis of 2-[3/4-((6-substituted-1-oxo-2,3-dihydro-1H-inden-2- ylidene)methyl)phenoxy]-N-(heteroaryl)acetamide derivatives and the investigation of their anticancer activity were studied. Methods: 2-(3/4-Hydroxybenzylidene)-6-substituted-2,3-dihydro-1H-inden-1-ones were reacted with suitable 2-chloroacetamides to give 2-[3/4-((6-substituted-1-oxo-2,3-dihydro-1H-inden-2-ylidene) methyl)phenoxy]-N-(heteroaryl)acetamide derivatives. Results: The structure elucidation of the newly synthesised 16 compounds was performed by IR, 1H-NMR, mass spectroscopic data and elemental analyse

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5

Bremner, JB, та W. Jaturonrusmee. "Manganese(III) Acetate-Induced Formation of a Fused, Chloro-Substituted β-Lactam Derivative From a Chloroacetamide". Australian Journal of Chemistry 43, № 8 (1990): 1461. http://dx.doi.org/10.1071/ch9901461.

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Reaction of 1-chloroacetyl-5-methoxy-2,3-dihydro-1H-dibenzo[de,h]quinoline (1) with manganese(III) acetate in acetic acid at 50° gave the novel fused spiro derivative 11-chloro-4-methoxy-1,2-dihydro-6H-azeto[2,1-f]dibenzo[de,h]quinoline-6,12(11H)-dione (6) in 21% yield, together with 5-methoxy-7H-dibenzo[de,h]quinolin-7-one (3), 5-methoxy-2,3-dihydro-7H-dibenzo[de,h]quinolin-7-one (4), and 1- chloroacetyl-5-methoxy-2,3-dihydro-1H-dibenzo[de,h]-quinolin-7-yl ethanoate (5) in 1, 3 and 44% yields respectively. Compound (5) was shown to be a precursor of (3), (4) and (6).

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6

Collins, David J., Timothy C. Hughes, and Wynona M. Johnson. "Dihydro-1,2,4-triazin-6(1H)-ones. III. Oxidation Products of 1-Methyl-3-phenyl- 4,5-dihydro-1,2,4-triazin-6(1H)-one." Australian Journal of Chemistry 52, no. 10 (1999): 971. http://dx.doi.org/10.1071/ch99047.

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1-Methyl-3-phenyl-4,5-dihydro-1,2,4-triazin-6(1H)-one (1) undergoes aerial oxidation to give a mixture of 1- methyl-3-phenyl-1,2,4-triazin-6(1H)-one (2) and 1-methyl-3-phenyl-1,4-dihydro-1,2,4-triazine-5,6-dione (3). The dehydro derivative (2) was cleanly prepared by the oxidation of (1) with 2,3-dichloro-5,6-dicyano-1,4- benzoquinone (ddq). The dehydro derivative (2) underwent a surprising rearrangement to the triazole (12) upon oxidation with OxoneR. Several attempts at unambiguous synthesis of the α-dicarbonyl derivative (3) were unsuccessful; it was obtained, together with the 1,4-dimethyl

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7

Santosh B. Gaikwad, Jagannath S. Godse, Amardeep R. Jadhao, and Kishore Puri. "Determination of Antimicrobial Effects of Dihydropyrano [2, 3-c] Pyrazole Derivatives Catalysed by MnFe₂O₄." International Journal of Scientific Research in Science and Technology 12, no. 4 (2025): 78–84. https://doi.org/10.32628/ijsrst251264.

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A recent study discovered antibacterial and antifungal compounds, highlighting their potential future importance in medicinal chemistry. The some Selected derivatives of dihydropyrano[2, 3-c]pyrazoles motif i.e. 6-amino-1,4-dihydro-3-methyl-4-(4-nitrophenyl)-1-phenylpyrano[2,3-c] pyrazole-5-carbonitrile shows excellent bacterial activity against Klebsiella pneumoniae and 6-amino-1,4-dihydro-4-(2,5-dimethoxyphenyl)-3-methyl -1-phenylpyrano[2,3-c]pyrazole-5-carbonitrile against Salmonella enterica serovar Typhimurium, whereas 6-amino-1,4-dihydro-4-(2-hydroxyphenyl)-3-methyl-1-phenylpyrano[2,3-c]

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8

Rádl, Stanislav. "Preparation of 1-Hydroxyxanthen-9(9H)-ones and 1-Hydroxyacridin-9(10H)-ones via Corresponding 3,4-Dihydro-1,9(2H)-diones." Collection of Czechoslovak Chemical Communications 60, no. 12 (1995): 2127–36. http://dx.doi.org/10.1135/cccc19952127.

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Target 10-cyclopropyl-7-fluoro-1-hydroxy-6-(4-methyl-1-piperazinyl)acridin-9(10H)-one (IVc) and 7-fluoro-1-hydroxy-6-(4-methyl-1-piperazinyl)-9H-xanthen-9-one (IVd) were obtained from corresponding difluoro derivatives IVa and IVb, respectively. These intermediates were synthesized via respective 3,4-dihydro-1,9(2H)-diones Va and Vb. Acridine derivative (10-cyclopropyl-6,7-difluoro-3,4-dihydro-1H-acridine-1,9(2H,10H)-dione, Va) was synthesized from 1-cyclopropyl-6,7-difluoroisatoic anhydride (XI) and xanthene derivative (6,7-difluoro-3,4-dihydro-1H-xanthen-1,9(2H)-dione, Vb) from cyclohexenone

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9

Rádl, Stanislav, and Lenka Kovářová. "Some reactions of N-propadienyl-4-quinolones." Collection of Czechoslovak Chemical Communications 56, no. 11 (1991): 2413–19. http://dx.doi.org/10.1135/cccc19912413.

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N-Alkylation of ethyl 6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (Vg) with 3-bromopropyne followed by acidic hydrolysis provided N-propyl derivative Ic which in alkaline media yielded N-propadienyl derivative IId. Propadienyl derivatives IIa and IIb treated with primary or secondary amines provided intermediates IIIa-IIIc which were hydrolyzed to N-acetonyl derivatives IVa and IVb, respectively. N-Benzylation of ethyl 7-chloro-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate (Va) followed by hydrolysis yielded 1-benzyl-7-chloro-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic ac

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10

Małecka, Magdalena, Lilianna Chęcińska, Joachim Kusz, Marta Biernacka, and Bogumiła Kupcewicz. "Interactions in flavanone and chalcone derivatives: Hirshfeld surface analysis, energy frameworks and global reactivity descriptors." Acta Crystallographica Section C Structural Chemistry 76, no. 3 (2020): 212–24. http://dx.doi.org/10.1107/s2053229620001503.

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The present study examines a series of flavanone and chalcone derivatives substituted with electron-withdrawing groups (Cl or Br) and electron-donating groups (OH, CH3 and OCH3), namely, 7-methoxy-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one, C16H14O3, 2-(4-methoxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-one, C16H14O3, 2-(4-methoxyphenyl)-6-methyl-3,4-dihydro-2H-1-benzopyran-4-one, C17H16O3, 2-(4-chlorophenyl)-3,4-dihydro-2H-1-benzopyran-4-one, C15H11ClO2, 8-bromo-6-methyl-2-phenyl-3,4-dihydro-2H-1-benzopyran-4-one, C16H13BrO2, (2E)-1-(2-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one, C16H14O3,

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11

Sridharan, M., K. J. Rajendra Prasad, A. Thomas Gunaseelan, A. Thiruvalluvar, and R. J. Butcher. "6-Chloro-3,4-dihydro-9H-carbazol-1(2H)-one." Acta Crystallographica Section E Structure Reports Online 64, no. 8 (2008): o1635. http://dx.doi.org/10.1107/s1600536808023441.

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12

Bakalova, Snezhana, and Ivanka Kavrakova. "Electronic Spectra and Photochemical Properties of Acetyldihydroquinolinones." Zeitschrift für Naturforschung B 47, no. 12 (1992): 1775–78. http://dx.doi.org/10.1515/znb-1992-1222.

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The absorption and luminescence properties of 6-acetyl-2,3-dihydro-4(1H)-quinolinone are described and compared to those of the parent 2,3-dihydro-4(1H)-quinolinone. The character of the electronic transitions is determined by PPP quantum chemical calculations.An N-acyl migration leading to the formation of 6-acetyl-2,3-dihydro-4(1H)-quinolinone takes place upon UV irradiation or heating with polyphosphoric acid of 1-acetyl-2,3-dihydro-4-(1H)-quinolinone. A radical mechanism of the photochemical rearrangement is proposed.

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13

Kayukov, Ya S., A. A. Grigor'ev, S. V. Karpov, O. V. Kayukova, and V. A. Tafeenko. "Heterocyclization of 2-nitrobenzoyl1,1,3,3-tetracyanopropenides by the action of hydrogen chloride in alcohol." Журнал органической химии 59, no. 5 (2023): 640–47. http://dx.doi.org/10.31857/s0514749223050117.

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The interaction of 2-[3(4)-nitrobenzoyl]-1,1,3,3-tetracyanopropenides with hydrogen chloride in alcohols leads to the corresponding 4-amino-1-alkoxy-1-[3(4)-nitrophenyl]-3-oxo-6-chloro-2,3-dihydro-1 H -pyrrolo[3,4- c ]pyridine-7-carbonitrilam, through the formation of intermediate 2-{2-hydroxy-2-[3(4)-nitrophenyl]-4-cyano-5alkoxy-1,2-dihydro-3 H -pyrrole-3-ylidene}malononitriles, which can be isolated in low yield. Carrying out the reaction in an aqueous-alcoholic medium makes it possible to obtain 4-amino-1-hydroxy-1-[3(4)-nitrophenyl]3-oxo-6-chloro-2,3-dihydro-1 H -pyrrolo[3,4- c ]pyridine-7

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14

Jasril, Jasril, Hilwan Yuda Teruna, Aisyah Aisyah, Nurlaili Nurlaili, and Rudi Hendra. "Microwave Assisted Synthesis and Evaluation of Toxicity and Antioxidant Activity of Pyrazoline Derivatives." Indonesian Journal of Chemistry 19, no. 3 (2019): 583. http://dx.doi.org/10.22146/ijc.34285.

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Four pyrazoline analogues, 3-(4-methoxyphenyl)-5-naphthalene-1-yl-1-phenyl-4,5-dihydro-pyrazole (3), 3-(4-methoxyphenyl)-5-naphthalene-1-yl-4,5-dihydro-1H-pyrazole (4), 3-(2-methoxyphenyl)-5-naphthalene-1-yl-1-phenyl-4,5-dihydro-pyrazole (5) and 3-(2-methoxyphenyl)-5-naphthalene-1-yl-4,5-dihydro-1H-pyrazole (6) were synthesized via intermolecular cyclization between substituted chalcones and hydrazine derivatives. The compounds were synthesized in two steps. In the first step, the chalcones were synthesized by Claisen-Schmidt reaction. In the second step, they were cyclized with some hydrazine

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15

Pragna, Thanki, Hingrajia Dhaval, and Modha Jayesh. "Synthesis and Characterization of Aroylhydrazino Derivatives of Pharmacologically Activepyrimidine-5-Carbonitrile." International Letters of Chemistry, Physics and Astronomy 39 (October 2014): 129–35. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.39.129.

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The target compound N'-(5-Cyano-4-(4-fluorophenyl)-1,6-dihydro-1-methyl-6-oxopyrimidin-2-yl)-4-methylbenzohydrazide have been synthesized by the condensation of 4-(4-Fluorophenyl)-2-hydrazinyl-1,6-dihydro-1-methyl-6-oxopyrimidine-5-carbonitrile with different aroylchlorides. The obtained products were characterized by 1H NMR, Mass and IR Spectra.

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16

Pragna, Thanki, Hingrajia Dhaval, and Modha Jayesh. "Synthesis and Characterization of Aroylhydrazino Derivatives of Pharmacologically Activepyrimidine-5-Carbonitrile." International Letters of Chemistry, Physics and Astronomy 39 (October 2, 2014): 129–35. http://dx.doi.org/10.56431/p-pb3q47.

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The target compound N'-(5-Cyano-4-(4-fluorophenyl)-1,6-dihydro-1-methyl-6-oxopyrimidin-2-yl)-4-methylbenzohydrazide have been synthesized by the condensation of 4-(4-Fluorophenyl)-2-hydrazinyl-1,6-dihydro-1-methyl-6-oxopyrimidine-5-carbonitrile with different aroylchlorides. The obtained products were characterized by 1H NMR, Mass and IR Spectra.

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17

Toan, Duong Ngoc, Nguyen Dinh Thanh, Mai Xuan Truong та Nguyen Minh Thao. "Synthesis of some 1H-1,5-benzodiazepine Series Containing Chromene Ring from α,β-Unsaturated Ketones of 6-Acetyl-5-Hydroxy-4-Methylcoumarin". Current Organic Synthesis 17, № 5 (2020): 404–10. http://dx.doi.org/10.2174/1570179417666200415152105.

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Background: Reaction of α,β-unsaturated ketones with o-phenylenediamine afforded corresponding 2,3-dihydro-1H-1,5-benzodiazepines. Objective: α,β-Unsaturated ketones of 6-acetyl-5-hydroxy-4-methylcoumarin are precursors for synthesis of 2,3-dihydro-1H-1,5-benzodiazepines by a reaction with o-phenylenediamine. Methods: Enones of 6-acetyl-5-hydroxy-4-methylcoumarin were prepared from this ketone and (un)substituted benzaldehydes in the presence of piperidine, triethylamine, or pyridine as a catalyst in absolute ethanol with 1:1 molar ratios, respectively. 2',3'-Dihydro-1H-1',5'-benzodiazepines w

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18

Armand, Joseph, Line Boulares, Christian Bellec, and Jean Pinson. "Preparation, chemical and electrochemical reduction of pyrido[2,3-b]quinoxalines and pyrido[3,4-b]quinoxalines." Canadian Journal of Chemistry 66, no. 6 (1988): 1500–1505. http://dx.doi.org/10.1139/v88-242.

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The reaction of 2,3-diaminopyridine with the dimeric 4,5-dimethylcyclohexa-3,5-dien-1,2-dione gives 7,8-dimethylpyrido[2,3-b]quinoxaline, 1, in good yields; in the same way 3,4-diaminopyridine gives the 7,8-dimethylpyrido[3,4-b]quinoxaline 2. The electrochemical reduction of 1 and 2 in hydroorganic medium gives the 5,10-dihydro compounds 6 and 7; 1 and 2 present a single 2e− polarographic wave, in contrast to phenazine which shows two monoelectronic waves. The catalytic hydrogenation of 1 and 2 gives 6 and 7 and does not involve the pyridinic ring as in the case of pyridopyrazines. AlLiH4 does

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19

Petříčková, Hana, Jan Čejka, Michal Hušák, et al. "Structure Types of Dihydroergotoxine Mesylates." Collection of Czechoslovak Chemical Communications 67, no. 4 (2002): 490–501. http://dx.doi.org/10.1135/cccc20020490.

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Three new crystal structures of dihydroergopeptines: dihydro-α-ergokryptine mesylate monohydrate acetone solvate (1), dihydro-α-ergokryptine mesylate monohydrate nitromethane solvate (2), and dihydroergocornine mesylate monohydrate methanol solvate (3) have been determined by X-ray single crystal diffraction. These structures were compared with published structures of dihydro-α-ergokryptine mesylate monohydrate ethanol solvate (4), dihydro-β-ergokryptine mesylate monohydrate methanol solvate (5), and dihydroergocristine mesylate monohydrate (6).

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20

Haydar, Yüksek, Karakaş Esra, Manap Sevda, and Özdemir Gül. "Synthesis and Characterization of Novel 2-Methoxy-6-[(1-acetyl-3-substituted-4,5-dihydro-1H-1,2,4-triazol-5-on-4-yl)-azomethine]phenyl-4-Methoxybenzoates." Chemistry Research Journal 6, no. 5 (2021): 57–61. https://doi.org/10.5281/zenodo.11802060.

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<strong>Abstract </strong>A series of novel 2-methoxy-6-[(1-acetyl-3-substituted-4,5-dihydro-1<em>H</em>-1,2,4-triazol-5-on-4-yl)-azomethine]phenyl 4-methoxybenzoates<strong> </strong><strong>(4)</strong> were synthesized from the reactions of 2-methoxy-6-[(3-substituted-4,5-dihydro-1<em>H</em>-1,2,4-triazol-5-on-4-yl)-azomethine]phenyl 4-methoxybenzoates (<strong>3</strong>), which were obtained by the reactions of 3-substituted-4-amino-4,5-dihydro-1<em>H</em>-1,2,4-triazol-5-ones (<strong>1</strong>) with 2-methoxy-3-(4-methoxybenzoxy)-benzaldehyde (<strong>2</strong>), with acetic anhydride

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21

Yadav, Pradeep, and Y. C. Joshi. "Synthesis and Spectral Study of Novel Norfloxacin Derivatives." E-Journal of Chemistry 5, s2 (2008): 1154–58. http://dx.doi.org/10.1155/2008/357073.

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Reaction of [1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-quinolone-3-carboxylic acid (norfloxacin) with thiazole / benzothiazole diazonium chloride to get new piperazine substituted norfloxacin derivative. These norfloxacin derivatives were further condensed with variousβ-diketone to get novel acid derivatives of 1-Ethyl-6-fluoro-4-oxo-7- [4 (thiazol-2-yldiazenyl)-piperzin-1-yl]-1,4-dihydro-quinoline-3-carboxylic acid (6a-e) and 7-(4-(benzo[d]thiazol-2-yldiazenyl)piperazin-1-yl)-1-ethyl-6-fluoro-4-oxo-1, 4-dihydroquinoline-3-carboxylic acid (6 f-j). Structures of these compounds were

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22

Shilin, Serhiy, Illya Lenko, Olga Shablykina, and Volodymyr Khilya. "6-Oxyindan-1-ones with amino acid fragments." French-Ukrainian Journal of Chemistry 6, no. 2 (2018): 18–26. http://dx.doi.org/10.17721/fujcv6i2p18-26.

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New indan-1-one derivatives (8 examples) with amino acid fragments were synthesized through the N-acylation of the amino acids by 2-(3-oxo-2,3-dihydro-1H-inden-5-yloxy)acetic acid using the method of activated N-hydroxysuccinimide esters. To obtain corresponding methyl esters (2 examples) two ways were possible: the N-acylation of the amino acid methyl esters by 2-(3-oxo-2,3-dihydro-1-inden-5-yloxy)acetic acid through the activated imidazole derivatives or methylation of the carboxylic function of preformed N-{[(1-oxoindan-6-yl)oxy]acetyl}amino acids.

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23

Werbovetz, Karl A., Edward S. Riccio, Anna Furimsky, et al. "Evaluation of Antitrypanosomal Dihydroquinolines for Hepatotoxicity, Mutagenicity, and Methemoglobin Formation In Vitro." International Journal of Toxicology 33, no. 4 (2014): 282–87. http://dx.doi.org/10.1177/1091581814533971.

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N1-Benzylated dihydroquinolin-6-ols and their corresponding esters display exceptional activity against African trypanosomes in vitro, and administration of members of this class of compounds to trypanosome-infected mice results in cures in a first-stage African trypanosomiasis model. Since a quinone imine intermediate has been implicated in the antiparasitic mechanism of action of these compounds, evaluation of the hepatotoxic, mutagenic, and methemoglobin-promoting effects of these agents was performed. 1-Benzyl-1,2-dihydro-2,2,4-trimethylquinolin-6-ol hydrochloride and 1-benzyl-1,2-dihydro-

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24

Krauze, A., Z. Andžāns, and G. Duburs. "Synthesis and Properties of Partially Hydrogenated Ethyl ([3,4']Bipyridin-6'-ylsulfanyl) Acetates." Latvian Journal of Chemistry 49, no. 1-4 (2010): 66–71. http://dx.doi.org/10.2478/v10161-010-0002-z.

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Synthesis and Properties of Partially Hydrogenated Ethyl ([3,4']Bipyridin-6'-ylsulfanyl) Acetates Ethyl 2'-hydroxy-1',2',3',4'-tetrahydro[3,4']bipyridine-3'-carboxylate 3 and the corresponding ethyl 1',4'-dihydro[3,4']bipyridine-3'-carboxylate 4 as potential cardiovascular agents have been prepared by alkylation of 2'-hydroxy-1',2',3',4'-tetrahydro[3,4']bipyridine-6'-thiolate 1 or betaine 2 with ethyl bromoacetate. The treatment of [3,4']bipyridine 4 with KOH/H2O gave diethyl 3-amino-4-(pyridin-3-yl)-4,7-dihydrothieno[2,3-b]-pyridine-2,5-dicarboxylate 5, but subsequent treatment of the remaini

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Rádl, Stanislav, and Viktor Zikán. "Synthesis and biological activity of some basic-substituted 4,9-dihydro-3-methyl-4-oxo-1H(2H)-pyrazolo[3,4-b]quinolines." Collection of Czechoslovak Chemical Communications 53, no. 8 (1988): 1812–19. http://dx.doi.org/10.1135/cccc19881812.

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Compounds Ia, Ib were obtained by an alkylation of 4,9-dihydro-6-hydroxy-1,3,9-trimethyl-4-oxo-1H-pyrazolo[3,4-b]quinoline (VIIb) with the respective dialkylaminoalkyl chloride. The same alkylation of 4,9-dihydro-6-hydroxy-2,3,9-trimethyl-4-oxo-2H-pyrazolo[3,4-b]quinoline (VIIIb) yielded compounds IIa and IIb. Similar alkylation of 4,9-dihydro-6-hydroxy-3,9-dimethyl-4-oxo-1H-pyrazolo[3,4-b]quinoline (IXa) and its 6-methoxy derivative (IXb) afforded IIIa-IIId. Compound IV was prepared from 4-chloro-3-methyl-1H-pyrazolo[3,4-b]quinoline (Xa) via its 1-(3-dimethylaminopropyl)derivative (Xb). Compo

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26

Glotova, Tatýana, Nadezhda Protsuk, Alexander Albanov, Valentin Lopyrev, and Gennadii Dolgushin. "Dithiobiuretes in reactions with electrophilic acetylenes. New derivatives of 1,3,5-dithiazines,-thiadiazines and-triazines as the products of competing reactions of nucleophilic cycloaddition." Open Chemistry 1, no. 3 (2003): 222–32. http://dx.doi.org/10.2478/bf02476225.

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AbstractThe nucleophilic addition of 2,4-dithiobiurete, 1- and 1,4-substituted 2,4-dithiobiuretes (2 a-e) with benzoylacetylene (1) has been studied. 2-(Benzoylmethyl)-4-(R1-imino)-6-(R2-imino)dihydro-4H-1,3,5-dithiazinium perchlorates (3 a-e) are obtained in glacial acetic acid (AcOH) in the presence of equimolar quantities of HClO4. The reaction of benzoylacetylene with 1,5-diphenyl-2,4-dithiobiurete in either of MeOH, C6H6, or MeCN solvents proceeds non-selectively to give a mixture of products such as 2-(benzoylmethyl)-4,6-di(phenylimino)dihydro-4H-1,3,5-dithiazine (5), 2-(benzoylmethyl)-4

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27

Rádl, Stanislav, and Viktor Zikán. "Synthesis of 1,2, and 9-methyl derivatives of 4,9-dihydro-6-methoxy-3-methyl-4-oxo-1H(2H)-pyrazolo[3,4-b]quinoline and 4,9-dihydro-6-hydroxy-3-methyl-4-oxo-1H(2H)-pyrazolo[3,4-b]quinoline and their antiviral activity." Collection of Czechoslovak Chemical Communications 52, no. 3 (1987): 788–92. http://dx.doi.org/10.1135/cccc19870788.

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The paper describes syntheses of 4,9-dihydro-6-methoxy-3-methyl-4-oxo-1H(2H)-pyrazolo[3,4-b]quinoline (Ia), its 1-methyl derivative (Ic), 1,9-dimethyl derivative (Ie), 2-methyl derivative (IIa), and 2,9-dimethyl derivative (IIc). Demethylation of these compounds with hydrobromic acid afforded 4,9-dihydro-6-hydroxy-3-methyl-4-oxo-1H(2H)-pyrazolo[3,4-b]quinoline (Ib), its 1-methyl derivative (Id), 1,9-dimethyl derivative (If), 2-methyl derivative (IIb), and 2,9-dimethyl derivative (IId) respectively. 4,9-Dihydro-6-hydroxy-3,9-dimethyl-4-oxo-1H-pyrazolo[3,4-b]quinoline (Ig) was prepared by demeth

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28

Jhustelin, Aimé. "Synthesis of 3-methoxy-6-phenyl-6, 6a-dihydro-[1] benzopyrano- [3, 4-b] [1] benzopyran." IOSR Journal of Applied Chemistry 4, no. 6 (2013): 27–30. http://dx.doi.org/10.9790/5736-0462730.

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29

Spiethoff, Wolf-Dieter. "Über Alkyl-4, 6-diamino-1, 2-dihydro-s-triazine." Zeitschrift für Chemie 7, no. 9 (2010): 342–43. http://dx.doi.org/10.1002/zfch.19670070907.

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30

Ahmed, Bahar, and Tawfeq A. Al-Howiriny. "Two New Hydroxy Chalcone Derivatives from Thymus cilicicus." Zeitschrift für Naturforschung B 62, no. 1 (2007): 121–24. http://dx.doi.org/10.1515/znb-2007-0118.

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The aerial part of Thymus cilicicus Linn. (Labiatae) has afforded two new hydroxy chalcone derivatives, characterized as 4, 2′, 4′, 6′, 7, 8-hexahydroxy-7 (8)-dihydro-chalcone (1), and 3, 4, 2′, 4′, 6′, 7, 8-heptahydroxy-7 (8)-dihydro-chalcone (2). The structures of the isolated compounds have been elucidated based on various spectral studies.

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31

R., PRASAD, та K. SRIVASTAVA P. "Synthesis of 1-Aryl-2-mercapto-4-phenyl-1 ,6-dihydro-1,3,5-triazine-6-thiones and their Addition Products with α,β-Unsaturated Carbonyl Compounds and Aryl Cyanamides as Antithyroidal Agen". Journal of Indian Chemical Society Vol. 69, Oct 1992 (1992): 664–66. https://doi.org/10.5281/zenodo.6020136.

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Department of Chemistry, Banaras _Hindu University, Varanasi-221 005 <em>Manuscript received 11 September 1991, revised 25 June 1992, accepted 3 July 1992</em>                                        Different 1-aryl-2-mercapto-4-phenyl-1,6-dihydro-1,3,5-triazine-6-thiones have been synthesised by the dealkylatien of 1-aryi2-benzylmercapto-4-phenyl-1, 6-dihydro-1, 3, 5-triazine-6-thione with thiourea and HCl. These mercapto triazine when treated with \(\propto\),β- unsaturated carbonyl

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32

Slyvka, N. Yu, L. M. Saliyeva, M. B. Litvinchuk, A. M. Grozav, N. D. Yakovychuk, and M. V. Vovk. "Regioselective synthesis of new (imidazo[2,1-b] [1,3]-thiazin-6-yl)-1,2,3-triazole-5-carboxylates as potential antimicrobial agents." Voprosy Khimii i Khimicheskoi Tekhnologii, no. 5 (October 2023): 114–22. http://dx.doi.org/10.32434/0321-4095-2023-150-5-114-122.

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The paper presents the results of the study on the interaction of azido(benz)imidazo[2,1-b][1,3]thiazines with acetylene carboxylates under non-catalytic conditions according to Huguesgen. It was established that the [3+2]-cyclocondensation of the specified reagents occurs regioselectively upon heating and without the use of a catalyst with the formation of a 1,4-addition product, alkyl 1-((benzo)imidazo[2,1-b][1,3]thiazine-6-yl)-1H-1,2,3-triazole-5-carboxylates 4a–g, the structure of which was thoroughly proved by the methods of 1H (13C) NMR spectroscopy and chromatography-mass spectrometry.

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33

Derrick, Ian A. R., Robert Livingstone, and Bruce J. McGreevy. "Solvolysis of 3,4-Dihalogeno-3,4-dihydro-2H-naphtho[1,2-b]pyrans and 1,2-Dihalogeno-2,3-dihydro-1H-naphtho[2,1 -b]pyrans." Journal of Chemical Research 23, no. 11 (1999): 640–41. http://dx.doi.org/10.1177/174751989902301102.

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Rates and activation parameters are obtained for the hydrolysis of trans-3 ax,4 ax-dihalogeno-3,4-dihydro-2 H-naphtho[1;2- b]pyrans and trans-1 ax,2 ax-dihalogeno-2,3-dihydro-1 H-naphtho[2,1-,6]pyrans1 and the methanolysis of the latter compounds in acetone–water and acetone–methanol, respectively.

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34

Bustos-Salgado, Paola, Berenice Andrade-Carrera, María Luisa Garduño-Ramírez, Helen Alvarado, and Ana Calpena-Campmany. "Quantification of one Prenylated Flavanone from Eysenhardtia platycarpa and four derivatives in Ex Vivo Human Skin Permeation Samples Applying a Validated HPLC Method." Biomolecules 10, no. 6 (2020): 889. http://dx.doi.org/10.3390/biom10060889.

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Prenylated flavanones are polyphenols that have diverse biological properties. The present paper focuses on a HPLC method validation for the quantification of prenylated flavanones (2S)-5,7-dihydroxy-6-(3-methyl-2-buten-1-yl)-2-phenyl-2,3-dihydro-4H-1Benzopyran-4-one 1 and derivatives (2S)-5,7-bis(acetyloxy)-6-(3-methyl-2-buten-1-yl)-2-phenyl-2,3-dihydro-4H-1-Benzopyran-4-one A; (2S)-5-hydroxy-7-methoxy-6-(3-methyl-2-buten-1-yl)-2-phenyl-2,3-dihydro-4H-1-Benzopyran-4-one B; (8S)-5-hydroxy-2,2-dimethyl-8-phenyl-3,4,7,8-tetrahydro-2H,6H-Benzo[1,2-b:5,4-bˈ]dipyran-6-one C; and (8S)-5-hydroxy-2,2-

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35

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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36

Dzurilla, Milan, Peter Kutschy, and Dušan Koščík. "A new method for preparation of 1-(4-substituted phenyl)-6-phenyl-2-thiouracils via cyclization of N-(4-substituted phenyl)-N'-3-phenylpropenoylthioureas and Dimroth rearrangement of 2-(4-substituted phenylimino)-6-phenyl-5,6-dihydro-4H-1,3-thiazin-4-ones." Collection of Czechoslovak Chemical Communications 52, no. 9 (1987): 2260–65. http://dx.doi.org/10.1135/cccc19872260.

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N-(4-Substituted phenyl)-N'-3-phenylpropenoylthioureas treated with lithium hydride afforded 1-(4-substituted phenyl)-6-phenyl-2-thiouracils; these could also be obtained by Dimroth rearrangement of 2-(4-substituted phenylimino)-6-phenyl-5,6-dihydro-4H-1,3-thiazin-4-ones under the same reaction conditions. 2-(4-Substituted phenylimino)-6-phenyl-5,6-dihydro-4H-1,3-thiazin-4-ones were synthesized from the corresponding thioureas under catalysis of boron trifluoride in chloroform.

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37

Xu, Feng, Zhenzhen Yang, Junrong Jiang, and Lei Shi. "1-[3-(4-Chlorophenyl)-6-methyl-1,6-dihydro-1,2,4,5-tetrazin-1-yl]ethanone." Acta Crystallographica Section E Structure Reports Online 66, no. 10 (2010): o2651. http://dx.doi.org/10.1107/s1600536810037839.

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38

Yang, Zhen-zhen, Feng Xu, and Hong-yun Chen. "1-[3-(4-Methoxyphenyl)-6-methyl-1,6-dihydro-1,2,4,5-tetrazin-1-yl]propanone." Acta Crystallographica Section E Structure Reports Online 66, no. 4 (2010): o969. http://dx.doi.org/10.1107/s1600536810011165.

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39

Nikitin, Kirill V., та Nonna P. Andryukhova. "Cyclization of 2-(2-bromoethoxy)-acetophenones and 5-(ω-haloalkoxy)-1,5-dihydro-2H-pyrrol-2-ones Formation of five- to eight-membered oxygen-containing heterocycles via intramolecular alkylation". Canadian Journal of Chemistry 82, № 5 (2004): 571–78. http://dx.doi.org/10.1139/v04-011.

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Under basic conditions (lithium diisopropylamide or sodium hydride in THF) 2-(2-bromoethoxy)-acetophenones were transformed to 3,4-dihydro[1]benzoxepin-5(2H)-ones (homochromanones) in high yields. The preparation of novel tetrahydropyrano[2,3-b]pyrrol-6(2H)-ones and 3,4-dihydro-2H-pyrrolo[2,1-b][1,3]oxazin-6(8aH)-ones and spiro compounds was performed using similar cyclization in moderate to good yields.Key words: cyclization, lithiation, spiro heterocycles.

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40

Weber, G., T. Hübner, A. Gieren, K. Burger, U. Wassmuth, and H. Partscht. "Röntgenstrukturanalyse von 2-[6-Fluor-1,4-dihydro-1-mesityl-2-phenyl-5-(trifluormethyl)-4-pyrimidinyl]-1,4-dihydro-1-mesityl-6-phenyl-4,4-bis(trifluormethyl)-1,3,5-triazin." Acta Crystallographica Section C Crystal Structure Communications 43, no. 1 (1987): 118–21. http://dx.doi.org/10.1107/s0108270187096793.

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41

RATNA, CHAKRABORTI (née DASGUPTA), DEB SOUMITRA та RANJAN GHATAK USHA. "Synthesis of α,β-Unsaturated Aldehydes by 1,3-Carbonyl Transposition through One Carbon Homologation. Part 2". Journal of Indian Chemical Society Vol. 62, Nov 1985 (1985): 883–86. https://doi.org/10.5281/zenodo.6325146.

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Department of Organic Chemistry, Indian Association for the Cultivation of Science, Jadavpur, Calcutta-700 082 The easily accessible 2-(diethoxymethyl)-6-methoxy-1-tetralone (1) on condensation with methylmagnesium iodide and benzylmagnesium chloride followed by treatment with BF<sub>3</sub>.Et<sub>2</sub>O affords 6-methoxy-1-methyl-3,4-dihydro-2-naphthaldehyde (2) and 1-benzyl-6-methoxy-3,4-dihydro-2-naphthaldehyde (3), respectively. The carbinols derived from the reaction of 2-(diethoxymethyl)-1-indanones (4a-4c) with methyllithium undergo smooth transformations to the respective 3-met

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42

Mutha, V. V. S. R. N. Anji Karun, Chakravarthy Chandra, B. Vijayabhaskar, et al. "Separation of Unprecedented Degradants of Domperidone by Ultra-Performance Convergence Chromatography and Their Structure Elucidation." Journal of Chromatographic Science 57, no. 9 (2019): 806–14. http://dx.doi.org/10.1093/chromsci/bmz066.

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Abstract Domperidone, a gastroprokinetic agent, is a common drug to treat emesis. It was subjected to acid, base-mediated hydrolysis, peroxide-mediated oxidation, photolysis and thermal degradation according to ICH guidelines to observe stability of the selected drug under the stress conditions. Although the drug is resistant to base hydrolysis, photolysis and thermal stressors, two degradants (DP-ISO1 and DP-ISO2) were formed in acid mediated hydrolysis. Oxidation with hydrogen peroxide also resulted in one product (DP-OX). All three degradants were isolated from the crude reaction mixture by

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43

Shubina, Larisa K., Tatyana N. Makarieva, Sergey A. Dyshlovoy, Sergey N. Fedorov, Pavel S. Dmitrenok, and Valentin A. Stonik. "Three New Aaptamines from the Marine Sponge Aaptos sp. and Their Proapoptotic Properties." Natural Product Communications 5, no. 12 (2010): 1934578X1000501. http://dx.doi.org/10.1177/1934578x1000501208.

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Three new aaptamine-type alkaloids, 2,3-dihydro-2,3-dioxoaaptamine (1), 6 -( N-morpholinyl)-4,5-dihydro-5-oxo-demethyl(oxy)aaptamine (2) and 3-(methylamino)demethyl(oxy)aaptamine (3), along with known aaptamines were isolated from the sponge Aaptos sp. Their structures were determined on the basis of detailed analysis of their 1D and 2D NMR spectroscopic and mass spectral data. The isolated compounds induced apoptosis in human leukemia THP-1 cells.

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44

Karpov, Sergey, Arthur Grigor’ev, Yakov Kayukov, Iuliia Gracheva, and Victor Tafeenko. "Cascade Regioselective Heterocyclization of 2-Acyl-1,1,3,3-tetracyanopropenides: Synthesis of Pyrrolo[3,4-c]pyridine and Pyrrolo[3,4-d]thieno[2,3-b]pyridine Derivatives." Synlett 28, no. 13 (2017): 1592–95. http://dx.doi.org/10.1055/s-0036-1588823.

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2-Acyl-1,1,3,3-tetracyanopropenides (ATCN) undergo cascade heterocyclization under the action of aliphatic thiols, resulting in the formation of 6-(alkylthio)-4-amino-1-aryl(alkyl)-1-hydroxy-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-7-carbonitriles. The involvement of methyl mercaptoacetate to this reaction leads to the formation of the methyl 4,8-diamino-1-aryl-1-hydroxy-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-d]thieno[2,3-b]pyridine-7-carboxylates, containing a new fused heterocyclic scaffold.

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45

Spiteller, Peter, Michael Spiteller, and Jovan Jovanovic. "NMR analysis of 6-(2?,3?-dihydro-1?H-inden-1?-yl)-1H-indene." Magnetic Resonance in Chemistry 40, no. 5 (2002): 371–76. http://dx.doi.org/10.1002/mrc.1021.

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46

Henao, J. A., A. Palma, V. V. Kouznetsov, and J. M. Delgado. "X-ray powder diffraction data for two new N-substituted 3,4-dihydrospiro-2(1H) quinolines." Powder Diffraction 14, no. 4 (1999): 249–52. http://dx.doi.org/10.1017/s0885715600010617.

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The X-ray powder diffraction patterns for two N-substituted tetrahydroquinolines are reported. N-(α-Chloroacetyl)-6-methoxy-3,4-dihydro-4-methylspiro[cyclohexane-1′,2(1H)quinoline], C18H24ClNO2, and N-(α-chloroacetyl)-6-chloro-3,4-dihydro-4-methylspiro[cyclohexane-1′,2(1H)-quinoline], C17H21Cl2NO are monoclinic, with refined unit cell parameters a=1.4471(3), b=0.9600(4), c=1.1948(3) nm, β=93.21(2)°, V=1.6573(6) nm3, Z=4, Dx=1.29 gcm−3, and a=1.4487(3), b=0.9878(2), c=1.1390(2) nm, β=91.66(2)°, V=1.6294(4) nm3, Z=4, and Dx=1.32 gcm−3, respectively, with space group P21/n (No. 14).Key words: pow

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47

Fun, Hoong-Kun, Suhana Arshad, P. C. Shyma, Balakrishna Kalluraya, and T. Arulmoli. "1-[2-(4-Chlorophenyl)-5-phenyl-2,3-dihydro-1,3,4-oxadiazol-3-yl]ethanone." Acta Crystallographica Section E Structure Reports Online 68, no. 6 (2012): o1901. http://dx.doi.org/10.1107/s1600536812023100.

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In the title compound, C16H14ClN3O2, the 2,3-dihydro-1,3,4-oxadiazole ring [maximum deviation = 0.030 (1) Å] and the pyridine ring [maximum deviation = 0.012 (1) Å] are inclined slightly to one another, making a dihedral angle of 11.91 (5)°. The chloro-substituted phenyl ring is almost perpendicular to the 2,3-dihydro-1,3,4-oxadiazole and pyridine rings at dihedral angles of 86.86 (5) and 75.26 (5)°, respectively. In the crystal, π–π [centroid–centroid distance = 3.7311 (6) Å] and C—H...π interactions are observed.

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48

Raposo, M. Manuela M., Alexandra M. B. Pereira, Ana M. F. Oliveira-Campos, and Patrick V. R. Shannon. "Studies on 5-Bromo-4,7-dimethylindene, an Intermediate in the Synthesis of 6-Bromo-5,8-dimethylisoquinoline." Journal of Chemical Research 23, no. 8 (1999): 466–67. http://dx.doi.org/10.1177/174751989902300806.

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We report the complete characterisation of all the precursors of 6-bromo-5,8-dimethylisoquinoline via the synthesis of Miller and Moock, and the synthesis of 6-bromo-4,7-dimethyl-2-(5′-Bromo-4’,7′-dimethyl)-2’,3′-dihydro-1' H-inden-1′-yl)-1 H-indene.

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49

Layne, Tanya H., William F. Reynolds, Stewart McLean, and Winston F. Tinto. "Secondary Metabolites from Clerodendrum Chinense." Natural Product Communications 3, no. 11 (2008): 1934578X0800301. http://dx.doi.org/10.1177/1934578x0800301108.

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Chemical studies carried out on Clerodendrum chinense yielded three new compounds including the steroid (22E, 24S)-stigmasta-4, 22, 25-trien-3-one (1), the flavone glycoside 7, 8, 4′-trihydroxyflavone-6-O-β-D-glucuronopyranoside (2) and the epimeric neo-clerodane 14, 15-dihydro-15ξ-hydroxyclerodendrin A (3). Two acetylated derivatives of compound 3-, 2α-acetoxy-14, 15-dihydro-15ξ-hydroxyclerodendrin A (4) and 2α-acetoxy-14, 15-dihydro-15ξ-methoxyclerodendrin A (5) were also prepared, which have not been reported previously. The structure of each compound was elucidated by spectroscopic means.

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50

Koffi, Jean-Michel Kouamé, Philomène Akoua Yao-Kouassi, Abdulmagid Alabdul Magid, Evariste Zachée Louis Akissi, and Laurence Voutquenne-Nazabadioko. "A new flavanocoumarin glucoside from the roots of Lannea kerstingii." International Journal of Biological and Chemical Sciences 16, no. 4 (2022): 1756–64. http://dx.doi.org/10.4314/ijbcs.v16i4.31.

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An undescribed phyllocoumarin-3-O-α-L-rhamnopyranoside 8 together with catechin 1, catechin-3-O-α-L-rhamnopyranoside 2, catechin-[7,8-bc]-4β-(3,4-dihydroxyphenyl)-dihydro-2(3H)-pyranon 3, 5-O-trans-p-coumaroylquinic acid 4, trans-p-coumaric acid 5, catechin-[5,6-e]-4β-(3,4-dihydroxyphenyl)-dihydro-2(3H)-pyranon 6, catechin-[5,6-e]-4α-(3,4-dihydroxyphenyl)-dihydro-2(3H)- pyranon 7, phyllocoumarin 9 and vaccinin A 10 were isolated from the roots of Lannea kerstingii. The structures of the compounds were established using NMR, IR and HR-ESI-MS spectroscopic analysis.

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