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Reactions of 2,3-dioxopyrrolo[2,1-a]isoquinolinecarboxylic acid esters and amides with nitrogen-centered nucleophiles

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Abstract

Reactions of ethyl 2,3-dioxopyrrolo[2,1-a]isoquinoline-1-carboxylates with active nitrogen-centered nucleophiles (phenylhydrazine, hydroxylamine, and benzylamine) involve opening of the pyrrole ring with formation of 2-(3,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-1-ylidene)-N′1,N′4-diphenyl-3-(2-phenylhydrazono) succinohydrazide, 5-(6,7-dimethoxy-3,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-1-ylidene)-2,3,4,5-tetrahydro-1H-1,2-oxazine-3,4,6-trione, and ethyl 4-benzylamino-2-(3,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-1-ylidene)-3,4-dioxobutanoate, respectively. Cyclic amides derived from 5,5-dimethyl-2,3-dioxo-2,3,5,6-tetrahydropyrrolo[2,1-a]isoquinoline-1-carboxylic acid react with benzylamine in a similar way. Reactions of the title compounds with weaker nucleophiles, such as semicarbazide and thiosemicarbazide, are not accompanied by opening of the pyrrole ring, and the products are the corresponding semicarbazones and thiosemicarbazones at the C2=O carbonyl group.

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Authors and Affiliations

  1. Perm State Pharmaceutical Academy, ul. Lenina 48, Perm, 614990, Russia

    O. V. Surikova, A. G. Mikhailovskii, N. N. Polygalova & M. I. Vakhrin

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  1. O. V. Surikova
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  2. A. G. Mikhailovskii
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  3. N. N. Polygalova
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  4. M. I. Vakhrin
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Correspondence to O. V. Surikova.

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Original Russian Text © O.V. Surikova, A.G. Mikhailovskii, N.N. Polygalova, M.I. Vakhrin, 2008, published in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 6, pp. 852–855.

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Surikova, O.V., Mikhailovskii, A.G., Polygalova, N.N. et al. Reactions of 2,3-dioxopyrrolo[2,1-a]isoquinolinecarboxylic acid esters and amides with nitrogen-centered nucleophiles. Russ J Org Chem 44, 840–844 (2008). https://doi.org/10.1134/S1070428008060109

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  • DOI: https://doi.org/10.1134/S1070428008060109

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