REACTIONS OF ENAMINO KETO ESTERS OF 1,2,3,4-TETRAHYDROISOQUINOLINE SERIES WITH NUCLEOPHILES
DOI:
https://doi.org/10.1007/2801Keywords:
3, 3-dimethyl-1-(5-thioxo-1, 5-dihydro-1, 2, 4-triazol-3-ylmethylidenecarbonyl)-1, 4-tetrahydroisoquinoline, methyl ester of 3-(3, 3-dimethyl-1, 4-tetrahydroisoquinolin-1-idene)pyruvic acid, nitrile of 2-cyano-4-dicyanomethylidene-5-(3, 4-tetrahydroisoquinolin-1-idene)-3-oxopentanoic acid, semicarbazide, thiosemicarbazide, annelation of the pyrrole ring, heterocyclization, ester condensation with malonodinitrileAbstract
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-tetrahydroisoquinoline, 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-oxopentanoic acid is formed.
How to Cite
Surikova, O. V.; Mikhailovskii, A. G.; Vakhrin, M. I. Chem. Heterocycl. Compd. 2010, 46, 179. [Khim. Geterotsikl. Soedin. 2010, 221.]
For this article in the English edition see DOI 10.1007/s10593-010-0489-y
