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Transformations of 2-trifluoroacetyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridines by the action of ethyl propynoate. A novel synthesis of 2-trifluoroacetyl-4,7,8,9-tetrahydro-1H-pyrrolo[2,3-d]azocines

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Abstract

2-Trifluoroacetyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridines reacted with ethyl propynoate in acetonitrile and methanol to give ethyl 2-trifluoroaceyl-4,7,8,9-tetrahydro-1H-pyrrolo[2,3-d]azocine-5-carboxylates. The reactions of 2-trifluoroacetyl-1-vinyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridines with ethyl propynoate in alcohols were accompanied by cleavage of the tetrahydropyridine fragment with formation of alkyl 3-{benzyl[2-(3-alkoxy-5-trifluoroacetyl-1-vinyl-1H-pyrrol-2-yl)ethyl]amino}acrylates.

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Authors and Affiliations

  1. Russian University of Peoples’ Friendship, ul. Miklukho-Maklaya 6, Moscow, 117198, Russia

    L. G. Voskresenskii, T. N. Borisova, T. A. Vorob’eva, O. V. Grishachkina, L. N. Kulikova, A. I. Chernyshev & A. V. Varlamov

Authors
  1. L. G. Voskresenskii
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  2. T. N. Borisova
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  3. T. A. Vorob’eva
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  4. O. V. Grishachkina
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  5. L. N. Kulikova
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  6. A. I. Chernyshev
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  7. A. V. Varlamov
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Original Russian Text © L.G. Voskresenskii, T.N. Borisova, T.A. Vorob’eva, O.V. Grishachkina, L.N. Kulikova, A.I. Chernyshev, A.V. Varlamov, 2006, published in Zhurnal Organicheskoi Khimii, 2006, Vol. 42, No. 12, pp. 1860–1864.

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Voskresenskii, L.G., Borisova, T.N., Vorob’eva, T.A. et al. Transformations of 2-trifluoroacetyl-4,5,6,7-tetrahydro-1H-pyrrolo[3,2-c]pyridines by the action of ethyl propynoate. A novel synthesis of 2-trifluoroacetyl-4,7,8,9-tetrahydro-1H-pyrrolo[2,3-d]azocines. Russ J Org Chem 42, 1851–1855 (2006). https://doi.org/10.1134/S1070428006120165

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  • DOI: https://doi.org/10.1134/S1070428006120165

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