One-step synthesis of thiazolo[3,2-a]pyridines by a multicomponent reaction of β-enaminonitriles, α,β-unsaturated aldehydes, and 2-aminothiol hydrochlorides

Perrino, Mónica Pérez; Villar‐Guerra, Rafael del; Sañudo, M. Carmen; Calvo, Luis; González‐Ortega, Alfonso

doi:10.1016/j.tet.2010.02.051

Cited by 15 publications

(3 citation statements)

References 32 publications

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“…As an extension of our study, the utilization of nitrile ( 2 ) for the synthesis of enaminonitrile analogues was also demonstrated. Enaminonitriles are versatile reagents, and their chemistry has recently received a considerable attention as precursors to, otherwise not readily obtainable heteroaromatics . We have recently reviewed the chemistry of the synthesis and application of heterocycles derived from enaminonitriles .…”

Section: Resultsmentioning

confidence: 99%

Efficient Syntheses of Some New Thiophene‐Based Heterocycles

El‐Mekabaty

Habib

Moawad

et al. 2016

Journal of Heterocyclic Chem

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In this effort, 2‐aminothiophene‐3‐carboxylate (1) was prepared using Gewald's methodology. This 2‐aminothiophene derivative was diazotized and coupled with malononitrile to obtain the nitrile derivative (2), which was utilized as key synthon for the synthesis of polyfunctionally substituted heterocycles via its reactions with some nitrogen and carbon nucleophiles. On the other hand, a facile and convenient syntheses of thiazolidinone, pyrrolidinone, and chromene derivatives incorporating thiophene moiety via the versatile, readily accessible 2‐aminothiophene‐3‐carboxylate (1) were also described.

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Section: Resultsmentioning

confidence: 99%

Efficient Syntheses of Some New Thiophene‐Based Heterocycles

El‐Mekabaty

Habib

Moawad

et al. 2016

Journal of Heterocyclic Chem

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“…The behavior of nitrile 1 toward secondary amine such as piperidine, as N ‐nucleophile, has been also investigated for a facile synthetic route to attain enaminonitrile analogs. Enaminonitriles are versatile reagents, and their chemistry has recently received considerable attention as precursors to otherwise not readily obtainable heteroaromatics . We have recently reviewed the chemistry of the synthesis and application of heterocycles derived from enaminonitriles .…”

Section: Resultsmentioning

confidence: 99%

Reactivity of 2‐Thiazolylhydrazonomalononitrile toward Carbon and Nitrogen Nucleophilic Reagents: Applications to the Synthesis of New Heterocycles

El‐Mekabaty

Habib

Moawad

et al. 2015

Journal of Heterocyclic Chem

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2‐Thiazolylhydrazonomalononitrile (1) was used as key intermediate for the synthesis of polyfunctionally substituted heterocycles (e.g. pyridazine, tetrazole, pyrimidines, 1,5‐benzo diazepine, benzoimidazo[1,2‐a]pyrimidine, triazolo[4,3‐a]pyrimidine, pyrazole, pyrazolo[1,5‐a]triazines, pyrazolo[1,5‐a]pyrimidine and 1,5‐benzoxazocine) incorporating thiazole moiety via its reactions with some carbon and nitrogen nucleophiles. Structures of the newly synthesized compounds were established by elemental analysis and spectral data. The mechanistic aspects for the formation of the new compounds were also discussed.

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“…[1][2][3][4][5][6][7][8][9][10] Several novel syntheses of azoles, azines, and azoloazines utilizing enaminonitriles as starting components have been reported by Elnagdi and coworkers. [11][12][13][14] On the other hand, the considerable biological and medicinal activities of thiazoles and those linked to different heterocycles through a carboxamide linkage initiated a considerable recent interest in the development of syntheses of these molecules.…”

Section: Introductionmentioning

confidence: 99%

Behavior of 2-cyano-3-(dimethylamino)-N-(4-phenylthiazol-2-yl)acrylamide towards some nitrogen nucleophiles

Bondock¹,

Tarhoni²,

Fadda³

2011

Arkivoc

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The versatile, hitherto unreported 2-cyano-3-(dimethylamino)-N-(4-phenylthiazol-2-yl)-acrylamide 2 was synthesized and allowed to react with hydroxylamine, hydrazine and guanidine to afford regioselectively the isoxazole 4, pyrazole 6 and pyrimidine 8 derivatives, respectively. The reaction of 2 with thiourea and / or ethyl glycinate in a basic medium afforded the regioisomeric pyrimidinethione 9 and 3,5-dioxo-1,4-diazepine-6-carbonitrile 14. Compound 2 reacts also with 2-amino-4-phenylthiazole, 2-amino-4-methylpyridine, 2-aminotetrazole, 2-aminobenzothiazole and 2-aminobenzimidazole to give the corresponding bridgehead nitrogen heterocycles namely thiazolo

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One-step synthesis of thiazolo[3,2-a]pyridines by a multicomponent reaction of β-enaminonitriles, α,β-unsaturated aldehydes, and 2-aminothiol hydrochlorides

Cited by 15 publications

References 32 publications

Efficient Syntheses of Some New Thiophene‐Based Heterocycles

Efficient Syntheses of Some New Thiophene‐Based Heterocycles

Reactivity of 2‐Thiazolylhydrazonomalononitrile toward Carbon and Nitrogen Nucleophilic Reagents: Applications to the Synthesis of New Heterocycles

Behavior of 2-cyano-3-(dimethylamino)-N-(4-phenylthiazol-2-yl)acrylamide towards some nitrogen nucleophiles

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