Synthesis and properties of 1-aroyl-5,5-dialkyl-2,3,5,6-tetrahydropyrrolo[ 2,1-a]isoquinoline-2,3-diones
- Authors: Mikhailovskii A.G.1, Yusov A.S.1, Gashkova O.V.1
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Affiliations:
- Perm State Pharmaceutical Academy
- Issue: Vol 52, No 2 (2016)
- Pages: 223-227
- Section: Article
- URL: https://journal-vniispk.ru/1070-4280/article/view/213716
- DOI: https://doi.org/10.1134/S1070428016020111
- ID: 213716
Cite item
Abstract
Acylation of 1-methyl-3,3-dialkyl-3,4-dihydroisoquinolines with acid chlorides afforded enaminoketones. Enaminophenylketones from the obtained series were reacted with oxalyl chloride to provide 1-benzoyl-5,5-dialkyl-2,3,5,6- tetrahydropyrrolo[2,1-a]isoquinoline- 2,3-diones. The reaction of the latter with binucleophiles leads to the opening of the pyrrole ring and to the heterocyclization: Under the effect of o-phenyldiamine qinoxaline is formed, 1,2-cyclohexanediamine provides the hexahydro-benzimidazole system, о-aminophenol gives benzoxazole, 3-hydroxy-2-amino-pyridine furnishes oxazolo[4,5-b]pyridine. In the reaction with hydrazine hydrate the acylation occurs with hydrazide formation.
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About the authors
A. G. Mikhailovskii
Perm State Pharmaceutical Academy
Author for correspondence.
Email: neorghim@pfa.ru
Russian Federation, ul. Polevaya 2, Perm, 614990
A. S. Yusov
Perm State Pharmaceutical Academy
Email: neorghim@pfa.ru
Russian Federation, ul. Polevaya 2, Perm, 614990
O. V. Gashkova
Perm State Pharmaceutical Academy
Email: neorghim@pfa.ru
Russian Federation, ul. Polevaya 2, Perm, 614990
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