Reactions of enamino keto esters of 1,2,3,4-tetrahydroisoquinoline series with nucleophiles

被引：0
作者：
O. V. Surikova
A. G. Mikhailovskii
M. I. Vakhrin
机构：
[1] Perm State Pharmaceutical Academy,
来源：
Chemistry of Heterocyclic Compounds | 2010年 / 46卷
关键词：
3,3-dimethyl-1-(5-thioxo-1,5-dihydro-1,2,4-triazol-3-ylmethylidenecarbonyl)-1,2,3,4-tetra-hydroisoquinoline; methyl ester of 3-(3,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-1-idene)pyruvic acid; nitrile of 2-cyano-4-dicyanomethylidene-5-(3,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-1-idene)-3-oxo-pentanoic acid; semicarbazide; thiosemicarbazide; annelation of the pyrrole ring; heterocyclization; ester condensation with malonodinitrile;
D O I：
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学科分类号：
摘要：
It has been shown that the reaction of the methyl ester of 3-(3,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-1-idene)pyruvic acid with thiosemicarbazide in glacial acetic acid leads to heterocyclization with the formation of 3,3-dimethyl-1-(5-thioxo-1,5-dihydro-1,2,4-triazol-3-ylmethylidenecarbonyl)-1,2,3,4-tetra-hydroisoquinoline, but the interaction with semicarbazide under the same conditions leads to annelation of the pyrrole ring. On condensation of the enamino keto ester with malonodinitrile, the nitrile of 2-cyano-4-dicyanomethylidene-5-(3,3-dimethyl-1,2,3.4-tetrahydroisoquinolin-1-idene)-3-oxo-pentanoic acid is formed.
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页码：179 / 183
页数：4
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