Partially hydrogenated pyridinechalcogenones

Литвинов, В. П.

doi:10.1007/bf02494257

Cited by 39 publications

(15 citation statements)

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“…Synthetic methods for this class of compounds are described in the numerous publications. 9,[12][13][14][15][141][142][143][144][145] However, the multicomponent synthesis of substituted 3cyanopyridine-2(1H)-(thi)ones from carbonyl compounds and derivatives of cyanoacetic acid has not been reviewed in the literature before now. Here we give some examples of such methods.…”

Section: Synthesis Of Substituted 3-cyanopyridine-2(1h)-(thi)onesmentioning

confidence: 99%

“…149 A multicomponent reaction of aldehydes, cyanothioacetamide, and 1,3-dicarbonyl compounds has found wideranging application in the synthesis of hydrogenated pyridine-2(1H)-thiones. 12,13,143 The synthesis is usually conducted in ethanol in the presence of excess organic base. Surprisingly, the structure of the reaction product is solely dependent upon the reaction conditions.…”

Section: Synthesis Of Substituted 3-cyanopyridine-2(1h)-(thi)onesmentioning

confidence: 99%

“…However, the information on multicomponent reactions of derivatives of cyanoacetic acid with carbonyl compounds has not been summarized before. The existing literature reviews about reactions of cyanoacetic acid derivatives with carbonyl compounds include random information on multicomponent transformations of these compounds, [9][10][11][12][13] thus demonstrating the necessity for a general and systematic summary of research data on this subject in a separate review.…”

Section: Introductionmentioning

confidence: 99%

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Multicomponent Reactions of Carbonyl Compounds and Derivatives of Cyanoacetic Acid: Synthesis of Carbo- and Heterocycles

Шестопалов¹,

Shestopalov²,

Rodinovskaya³

2008

Synthesis

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Section: Synthesis Of Substituted 3-cyanopyridine-2(1h)-(thi)onesmentioning

confidence: 99%

Section: Synthesis Of Substituted 3-cyanopyridine-2(1h)-(thi)onesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Multicomponent Reactions of Carbonyl Compounds and Derivatives of Cyanoacetic Acid: Synthesis of Carbo- and Heterocycles

Шестопалов¹,

Shestopalov²,

Rodinovskaya³

2008

Synthesis

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“…Aminothiophenes react with 5,5′‐dimethyl N ‐cyanoiminocarbodithioate to give isothioureas followed by cyclization in the presence of amine if its ester substituent or by heating with a base if its amino substituted (route h) to yield A . Thienylthioureas (route i) are prepared by reactions of vic‐amino(ethoxycarbonyl)‐thiophenes with isothiocyanates followed by pyrimidine ring closure upon treatment with an ethanoholic solution of HCl or ethanolic alkali followed by acidification of the mixture with hydrochloric acid . Condensation of ethyl 2‐aminothiophene‐3‐carboxylate with SCNCO 2 Et followed by treatment of the produced intermediate with NaOEt afforded A (route b) .…”

Section: Introductionmentioning

confidence: 99%

Medicinal Attributes of Thienopyrimidine Based Scaffold Targeting Tyrosine Kinases and Their Potential Anticancer Activities

Ghith

Ismail

Youssef

et al. 2017

Archiv der Pharmazie

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Thienopyrimidines (TP), comprising a thiophene ring fused with pyrimidine, are famous bioisosteres to purines, an essential part of the human metabolome. This scaffold has become an interesting structural element in the development of pharmaceutical compounds, due to their wide spectrum applications as cytotoxic agents against different types of human cancer cell lines, cGMP phosphodiesterase inhibitors, and anti-viral, anti-inflammatory, and anti-microbial agents. The structural similarity of this scaffold with adenine made it an excellent moiety to be used in the design of kinase inhibitors. This review focuses on the chemistry of thienopyrimidine derivatives, their potential activities against various kinases, and their structure-activity relationship studies.

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“…being used in the treatment of cardiovascular disease (calcium antagonist). 1,2 This applies especially to 4-aryl-or hetaryl-substituted 1,4-dihydropyridines. One of the well-known cardiovascular agents of this kind is Nifedipine 1.…”

Section: Introductionmentioning

confidence: 99%

Reaction of 3-aminocyclohex-2-en-1-ones with arylidenemalononitriles: synthesis of N-substituted 1,4,5,6,7,8-hexahydroquinolin-5-ones

Lichitsky¹,

Dudinov²,

Krayushkin³

2002

Arkivoc

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Reaction of 3-aminocyclohex-2-en-1-ones with AbstractThe reaction of 3-amino-and 3-hydrazinocyclohex-2-en-1-ones derived from cyclohexane-1,3-diones and an appropriate amine or hydrazine with 2-arylidenemalononitriles was investigated. An efficient method for the synthesis of N-substituted 1,4,5,6,7,8-hexahydroquinolin-5-ones was elaborated.Keywords: 3-Aminocyclohex-2-en-1-ones, 3-hydrazinocyclohex-2-en-1-ones, 2-arylidenemalononitriles, 1,4,5,6,7,8-hexahydroquinolin-5-ones Introduction 1,4-Dihydropyridines have received considerable attention because of their pivotal role in various biological processes. Numerous derivatives of dihydropyridines have been reported to have wide biological activity, e.g. being used in the treatment of cardiovascular disease (calcium antagonist).1,2 This applies especially to 4-aryl-or hetaryl-substituted 1,4-dihydropyridines. One of the well-known cardiovascular agents of this kind is Nifedipine 1.It is conceivable that fused 1,4-dihydropyridines of type 2 with different substituents R 1 at involving the reaction of cyclic enaminoketones 3 with arylidene derivatives of malononitrile 4. This method allows the attachment of substituents to the nitrogen atom in the course of the preparation of the enaminoketones 3. It has been shown that heating of 3-anilino-5,5-dimethylcyclohex-2-en-1-one 3a with 2-benzylidenemalononitrile 4a in alcohol and in the presence of catalytic amounts of a base yields the N-phenyl-substituted hexahydroquinoline 5a (Scheme 1).3 Scheme 1Recently, we have extended this approach to the reaction of 3-(2-phenyl-hydrazino)cyclohex-2-en-3-one 3b with 2-(4-bromobenzylidene)malononitrile 4b. 4 The product of this reaction, the N-(phenylamino)hexahydroquinoline derivative 5b was found to undergo an interesting diastereoselective rearrangement forming the previously unknown heterocyclic system 6 with partially hydrogenated fused indole and pyridine moieties 5 (Scheme 2). Scheme 2The present paper presents the results of a somewhat extended investigation of the condensation of N-substituted and N-unsubstituted 3-aminocyclohex-2-en-1-ones 3 with 2-arylidenemalononitriles 4 resulting in 4-aryl-substituted hexahydroquinolin-5-ones 4 with various substituents at the ring nitrogen atom. The optimal reaction conditions for the conversion Results and DiscussionThe N-unsubstituted 3-aminocyclohex-2-en-1-one 3c readily reacted with 2-benzylidenemalononitrile 4a upon short heating of a benzene solution in the presence of catalytic amounts of piperidine and afforded the N-unsubstituted hexahydroquinoline derivative 5c. The reaction proceeded in two steps: Heating the mixture of the reactants without a base catalyst yielded the adduct 7, which was isolated and identified. Only in the presence of a base (piperidine) the intramolecular cyclization was induced leading to the hexahydroquinolin-5-one 5c (Scheme 3). Scheme 3N-Aryl substituents decrease the nucleophilicity of enaminoketones 3 toward 2-arylidenemalononitriles 4; a base catalyst was required to achieve the formation of ...

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Partially hydrogenated pyridinechalcogenones

Abstract: Data on the methods of synthesis, structure, and reactivity of partially hydrogenated 3-cyanopyridin-2(l//)-ones, -thiones, and selenones, which are promising substrates in the synthesis of annelated heterocycles containing a partially hydrogenated pyridine ring, are analyzed.

Cited by 39 publications

References 26 publications

Multicomponent Reactions of Carbonyl Compounds and Derivatives of Cyanoacetic Acid: Synthesis of Carbo- and Heterocycles

Multicomponent Reactions of Carbonyl Compounds and Derivatives of Cyanoacetic Acid: Synthesis of Carbo- and Heterocycles

Medicinal Attributes of Thienopyrimidine Based Scaffold Targeting Tyrosine Kinases and Their Potential Anticancer Activities

Reaction of 3-aminocyclohex-2-en-1-ones with arylidenemalononitriles: synthesis of N-substituted 1,4,5,6,7,8-hexahydroquinolin-5-ones

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Partially hydrogenated pyridinechalcogenones

Abstract: Data on the methods of synthesis, structure, and reactivity of partially hydrogenated 3-cyanopyridin-2(l//)-ones, -thiones, and selenones, which are promising substrates in the synthesis of annelated heterocycles containing a partially hydrogenated pyridine ring, are analyzed.

Cited by 39 publications

References 26 publications

Multicomponent Reactions of Carbonyl Compounds and Derivatives of Cyanoacetic Acid: Synthesis of Carbo- and Heterocycles

Multicomponent Reactions of Carbonyl Compounds and Derivatives of Cyanoacetic Acid: Synthesis of Carbo- and Heterocycles

Medicinal Attributes of Thienopyrimidine Based Scaffold Targeting Tyrosine Kinases and Their Potential Anticancer Activities

Reaction of 3-aminocyclohex-2-en-1-ones with arylidene­malononitriles: synthesis of N-substituted 1,4,5,6,7,8-hexahydroquinolin-5-ones

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Reaction of 3-aminocyclohex-2-en-1-ones with arylidenemalononitriles: synthesis of N-substituted 1,4,5,6,7,8-hexahydroquinolin-5-ones