Year 2005, Month 5 (Section Brief Communications, Page 1335)
Three-component condensation in the synthesis of substituted
tetrahydropyridinethiolates*
K. A. Frolov (a), V. V. Dotsenko (a), S. G. Krivokolysko (a), and V. P. Litvinov (b)
Multicomponent cyclocondensation of Meldrum´s acid, 2-chlorobenzaldehyde, and
N-(4-bromophenyl)-3-amino-3-thioxopropanamide in the presence of N-methylmorpholine afforded N-methylmorpholinium 3-[N-(4-bromophenyl)carbamoyl]-4-(2-chlorophenyl)-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolate in 65% yield. When treated with dilute HCl, the thiolate easily transformed into N-(4-bromophenyl)-4-(2-chlorophenyl)-2-oxo-6-thioxo-piperidine-5-carboxamide, which reacted with alkyl halides to give products of regioselective S-alkylation in high yields.
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