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The Annelation for Enaminoureides of 3,3-Dimethyl-1,2,3,4-tetrahydroisoquinoline Series by Action of Oxalyl Chloride and Ninhydrin

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Abstract

By reaction of Ritter cyclization of cyanoacetylureas with dimethylbenzylcarbinoles the corresponding enaminoureides were obtained, derivatives of 3,3-dimethyl-1,2,3,4-tetrahydroisoquinoline. The polyfunctional character of obtained compounds is confirmed by the structure of products of reaction with some electrophiles: phenyl isocyanate reacts at the γ-C atom of enamine and CONH2 group of urea, under the action of oxalyl chloride annelation of a pyrrole cycle occurs with the formation of a derivative of 2,3-dioxopyrrolo[2,1-a]isoquinoline. Reaction with ninhydrin occurs similary with enaminoamides having hydrogen atoms at the amide nitrogen: a pyrrole ring is fused with the formation of a system of indeno[1,2-b]pyrrole.

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Authors and Affiliations

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

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

  2. Institute of Problems of Chemical Physics, Russian Academy of Sciences, Chernogolovka, Moscow oblast, 142432, Russia

    D. V. Korchagin

Authors
  1. A. G. Mikhailovskii
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  2. A. S. Yusov
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  3. D. V. Korchagin
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  4. O. V. Gashkova
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Correspondence to O. V. Gashkova.

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Original Russian Text © A.G. Mikhailovskii, A.S. Yusov, D.V. Korchagin, O.V. Gashkova, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 5, pp. 710–715.

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Mikhailovskii, A.G., Yusov, A.S., Korchagin, D.V. et al. The Annelation for Enaminoureides of 3,3-Dimethyl-1,2,3,4-tetrahydroisoquinoline Series by Action of Oxalyl Chloride and Ninhydrin. Russ J Org Chem 54, 713–718 (2018). https://doi.org/10.1134/S107042801805007X

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  • DOI: https://doi.org/10.1134/S107042801805007X

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