Recyclization of morpholinium 3,4- trans-4-aryl-5-cyano-2-hydroxy-3-nitro-1,2,3,4-tetrahydropyridine-6-thiolates to 2-acylamino-5-amino-4-aryl-3-cyanothiophenes. Molecular and crystal structures of 5-amino-3-cyano-2-(4-methylbenzamido)-4-(2-thienyl)-thiophene

2-Acylamino-5-amino-4-aryl-3-cyanothiophenes were synthesized by the reaction of arylidenecyanothioacetamides with α-nitroketones or by the three-component reaction of aromatic aldehydes, α-nitroketones, and cyanothioacetamide, or the reaction of 3-(4-chlorophenyl)-2-nitro-1-phenyl-2-propen-1-one wi...

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Published inTetrahedron Vol. 58; no. 21; pp. 4273 - 4282
Main Authors Rodinovskaya, Ludmila A., Shestopalov, Anatoly M., Chunikhin, Konstantin S.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 20.05.2002
Elsevier
Subjects
Chemistry
Chemistry, Organic
Michael adduct
nitrocarbonyl compounds
Physical Sciences
Science & Technology
nitrocarbonyl compounds
Michael adduct
NITRILE CYCLIZATION
STEREOSELECTIVE SYNTHESIS
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Summary:2-Acylamino-5-amino-4-aryl-3-cyanothiophenes were synthesized by the reaction of arylidenecyanothioacetamides with α-nitroketones or by the three-component reaction of aromatic aldehydes, α-nitroketones, and cyanothioacetamide, or the reaction of 3-(4-chlorophenyl)-2-nitro-1-phenyl-2-propen-1-one with cyanothioacetamide in the presence of morpholine. These diaminothiophenes are formed via the recyclization stage of the primarily formed tetrahydropyridines, morpholinium 3,4- trans-4-aryl-5-cyano-2-hydroxy-3-nitro-1,2,3,4-tetrahydropyridine-6-thiolates. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(02)00361-7