Synthesis and properties of 1-aroyl-5,5-dialkyl-2,3,5,6-tetrahydropyrrolo[ 2,1-a]isoquinoline-2,3-diones


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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.

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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