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Reaction of ninhydrin with enamino amides of the 3,3-dimethyl-1,2,3,4-tetrahydroisoquinoline series and drotaverine

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Abstract

“Push–pull” enamines of the 1,2,3,4-tetrahydroisoquinoline series, 2-(3,3-dimethyl-1,2,3,4-tetrahydroisoquinolin- 1-ylidene)acetamides, reacted as 1,3-binucleophiles with ninhydrin to form tricyclic tetrahydroindeno[1,2-b]pyrrole system. The nucleophilic centers in the enamines were the amide NH2 group and ß-carbon atom of the enamine fragment. The reaction of ninhydrin with 2-[2,2-dimethyl-2,3-dihydrobenzo[f]-isoquinolin-1(4H)-ylidene]-1-(pyrrolidin-1-yl)ethanone involved only addition to the ß-carbon atom of the enamine fragment. The different reaction directions were rationalized by steric effect of two methyl groups in position 3 of the isoquinoline ring. The Knoevenagel condensation product was obtained by the reaction of ninhydrin with drotaverine (base). The structure of the 1,3-addition product, (3aS,8bS,Z)-{2,2-dimethyl-2,3- dihydrobenzo[f]isoquinolin-4(1H)-ylidene}-3a,8b-dihydroxy-1,3,3a,8b-tetrahydroindeno[1,2-b]pyrrole-2,4-dione, was confirmed by X-ray analysis.

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Authors and Affiliations

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

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

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

    D. V. Korchagin

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

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Original Russian Text © A.G. Mikhailovskii, D.V. Korchagin, O.V. Gashkova, A.S. Yusov, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 9, pp. 1351–1355.

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Mikhailovskii, A.G., Korchagin, D.V., Gashkova, O.V. et al. Reaction of ninhydrin with enamino amides of the 3,3-dimethyl-1,2,3,4-tetrahydroisoquinoline series and drotaverine. Russ J Org Chem 52, 1339–1343 (2016). https://doi.org/10.1134/S1070428016090153

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  • DOI: https://doi.org/10.1134/S1070428016090153

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