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Regio- and diastereoselective cycloaddition of stable cyclic azomethine imines to N-arylitaconimides

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Abstract

1,3-Dipolar cycloaddition of stable N,N′- and C,N-cyclic azomethine imines based respectively on pyrazolidin-3-one and 3,4-dihydroisoquinoline to N-arylitaconimides proceeds strictly regioselectively resulting in spiro-joint heterocycles in good yields. The regioselectivity of the addition of N,N′-cyclic azomethine imines is reversed with respect to that of C,N-cyclic azomethine imines. The diastereoselectivity of the cycloaddition depends apparently on the substituents at the central nitrogen atom in the azomethine imine fragment.

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Authors and Affiliations

  1. St. Petersburg State University, Universitetskii pr. 26, St. Petersburg, 198504, Russia

    Yu. B. Koptelov, A. P. Molchanov & R. R. Kostikov

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  1. Yu. B. Koptelov
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  2. A. P. Molchanov
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  3. R. R. Kostikov
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Correspondence to Yu. B. Koptelov.

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Original Russian Text © Yu.B. Koptelov, A.P. Molchanov, R.R. Kostikov, 2015, published in Zhurnal Organicheskoi Khimii, 2015, Vol. 51, No. 8, pp. 1154–1162.

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Koptelov, Y.B., Molchanov, A.P. & Kostikov, R.R. Regio- and diastereoselective cycloaddition of stable cyclic azomethine imines to N-arylitaconimides. Russ J Org Chem 51, 1134–1143 (2015). https://doi.org/10.1134/S1070428015080126

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  • DOI: https://doi.org/10.1134/S1070428015080126

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