- On the regioselectivity of the reaction of cyanothioacetamide with 2-acetylcyclo-hexanone, 2-acetylcyclopentanone, and 2-acetyl-1-(morpholin-4-yl)- 1-cycloalkenes
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It has been established that the interaction of cyanothioacetamide with 2-acetylcyclohexanone, 2-acetylcyclopentanone, or their enamines (2-acetyl-1-(morpholin-4-yl)-1-cycloalkenes) contrary to the literature data have a non-regiospecific character and leads to the formation of mixtures of 3-cyano-4-methyl-5,6-tri(tetra)methylenepyridine-2(1H)-thiones and 3-cyano-6-methyl-4,5-tri(tetra)methylene-pyridine-2(1H)-thiones with a predominance of the latter.
- Dotsenko,Krivokolysko,Polovinko,Litvinov
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experimental part
p. 309 - 319
(2012/09/11)
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- Synthesis of condensed heteroaromatics: Novel synthesis of aminoquinolizinone derivatives as anti-HIV agents
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New routes for the synthesis of aminoquinolizinone derivatives with interesting biological activities are reported. Reactions enaminones 2 and 9 with malononitrile affords aminoquinolizinone derivatives 7a and 7b. Fusion of acetylcyclohexanone (1) with DMF DMA and ethyl cyanoacetate affords only product 11. Treatment of the latter product with malononitrile affords the aminoquinolizinone derivative 15. Reaction of chalcone 17 with malononitrile furnished the product 22. Condensation of (1) with arylidenemalononitrile 23a,b affords compounds 28a,b, respectively. The structure of the newly synthesized compounds was elucidated by elemental analyses and 1H NMR spectra and in some cases by 13C NMR investigation.
- Al-Omran, Fatima,Elassar, Abdel-Zaher A,El-Khair, Adel A
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p. 10163 - 10170
(2007/10/03)
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- CYCLIZATION OF NITRILES. XIV. SYNTHESIS AND REACTIONS OF 1-ALKYL-4-CYANO-5,6,7,8-TETRAHYDRO-3(2H)-ISOQUINOLINETHIONES AND SOME OF THEIR ANALOGS
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1-Alkyl-4-cyano-5,6,7,8-tetrahydro-3(2H)-isoquinolinethiones and 6-methyl-4,5-trimethylene-3-cyano-2(1H)-pyridinethione were synthesized by the reaction of cyclic enamino ketones and 1,3-diketones with nitriles containing an active methylene group.The products are readily alkylated by halogen derivatives of the sulfur atom with the formation of substituted 3-alkylthio-4-cyano-5,6,7,8-tetrahydroisoquinolines, 3-aminothienopyridines, and 3-aminothienoquinolines, which were used in the synthesis of various heterocyclic systems.The corresponding 1-alkyl-4-cyano-5,6,7,8-tetrahydro-3(2H)-isoquinolines are alkylated preferentially at the ring nitrogen atom.
- Sharanin, Yu. A.,Shestopalov, A. M.,Promonenkov, V. K.,Rodinovskaya, L. A.
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p. 2216 - 2224
(2007/10/02)
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