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Reactions of ethyl 6,6-dialkyl-8,9-dioxo-5,6,8,9-tetrahydrobenzo[f]pyrrolo[2,1-a]isoquinoline-10-carboxylates with N-nucleophiles

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Abstract

Reaction of enaminoesters, derivatives of 2,2-dialkyl-1,2,3,4-tetrahydrobenzo[f]isoquinoline, with oxalyl chloride leads to the formation of ethyl 6,6-dialkyl-8,9-dioxo-5,6,8,9-tetrahydrobenzo[f]pyrrolo[2,1-a]-isoquinoline-10-carboxylates. At reaction of the latter with ammonia and cyclic amines opening of pyrroledione cycle occurs and the formation of enaminoketoamides, and the reaction with o-phenylenediamine furnishes a fragment of benzimidazole. Hydroxylamine behaves as binucleophile and attacks not only lactam, but also the ester group, affording heterocyclic system of isoxazine-3,4,6-trione.

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Authors and Affiliations

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

    А. G. Mikhailovskii, А. S. Yusov & О. V. Gashkova

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  1. А. G. Mikhailovskii
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  2. А. S. Yusov
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  3. О. V. Gashkova
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Correspondence to А. G. Mikhailovskii.

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Original Russian Text © А.G. Mikhailovskii, А.S. Yusov, О.V. Gashkova, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 8, pp. 1207–1210.

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Mikhailovskii, А.G., Yusov, А.S. & Gashkova, О.V. Reactions of ethyl 6,6-dialkyl-8,9-dioxo-5,6,8,9-tetrahydrobenzo[f]pyrrolo[2,1-a]isoquinoline-10-carboxylates with N-nucleophiles. Russ J Org Chem 53, 1222–1225 (2017). https://doi.org/10.1134/S1070428017080103

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  • DOI: https://doi.org/10.1134/S1070428017080103

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