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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.

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Authors and Affiliations

  1. Perm State Pharmaceutical Academy, ul. Polevaya 2, Perm, 614990, Russia

    A. G. Mikhailovskii, A. S. Yusov & O. V. Gashkova

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  1. A. G. Mikhailovskii
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  2. A. S. Yusov
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  3. O. V. Gashkova
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Correspondence to A. G. Mikhailovskii.

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Original Russian Text © А.G. Mikhailovskii, А.S. Yusov, О.V. Gashkova, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 2, pp. 240–244.

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Mikhailovskii, A.G., Yusov, A.S. & Gashkova, O.V. Synthesis and properties of 1-aroyl-5,5-dialkyl-2,3,5,6-tetrahydropyrrolo[ 2,1-a]isoquinoline-2,3-diones. Russ J Org Chem 52, 223–227 (2016). https://doi.org/10.1134/S1070428016020111

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  • DOI: https://doi.org/10.1134/S1070428016020111

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