Synthesis of isoquinoline derivatives of quinoxalin-2-one from pyrrolo[2,1-a]isoquinoline-2,3-diones and o-phenylenediamine |
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| Authors: | O. V. Surikova Z. G. Aliev N. N. Polygalova A. G. Mikhailovskii M. I. Vakhrin |
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| Affiliation: | (1) Perm State Pharmaceutical Academy, ul. Lenina 48, Perm, 614990, Russia;(2) Institute of Chemical Physics Problems, Russian Academy of Sciences, Chernogolovka, Moscow oblast, Russia |
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| Abstract: | ![]()
Reactions of 5,5-dialkyl-2,3,4,5-tetrahydropyrrolo[2,1-a]isoquinoline-2,3-diones with o-phenylenediamine in the presence of a catalytic amount of hydrogen chloride or p-toluenesulfonic acid involved opening of the pyrrole ring with formation of 3-(3,3-dialkyl-1,2,3,4-tetrahydroisoquinolin-1-ylidenemethyl)quinoxalin-2(1H)-ones. The presence of an enamine fragment in the products was confirmed by reaction with oxalyl chloride. |
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