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Thermal opening of the diaziridine fragment in 1-methyl-and 1,3,3-trimethyl-1,3,4,8b-tetrahydro-[1,2]diazirino[3,1-a]isoquinolines in the presence of n-arylmaleimides

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Abstract

The thermal opening of the diaziridine ring in 1-methyl-and 1,3,3-trimethyl-1,3,4,8b-tetra-hydro[1,2]diazirino[3,1-a]isoquinolines in the presence of N-arylmaleimides leads to the predominant or exclusive formation of the trans isomers of the products of 1,3-dipolar cycloaddition. In the absence of dipolarophile, the conversion of the starting diaziridines is incomplete over the same time period, while the thermolysis products are N-[3,4-dihydro-2(1H)-isoquinolyl]-and N-[3,3-dimethyl-3,4-di-hydro-2(1H)-isoquinolyl]-N-methyleneamines formed as the result of isomerization of intermediate labile azomethineimines.

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Authors and Affiliations

  1. St. Petersburg State University, St. Petersburg, 198504, Russia

    Yu. B. Koptelov, S. P. Saik & A. P. Molchanov

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  1. Yu. B. Koptelov
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  2. S. P. Saik
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  3. A. P. Molchanov
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Correspondence to Yu. B. Koptelov.

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Dedicated to the memory of A. A. Potekhin.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1071–1079, July, 2008.

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Koptelov, Y.B., Saik, S.P. & Molchanov, A.P. Thermal opening of the diaziridine fragment in 1-methyl-and 1,3,3-trimethyl-1,3,4,8b-tetrahydro-[1,2]diazirino[3,1-a]isoquinolines in the presence of n-arylmaleimides. Chem Heterocycl Comp 44, 860–867 (2008). https://doi.org/10.1007/s10593-008-0122-5

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  • DOI: https://doi.org/10.1007/s10593-008-0122-5

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