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Research on 1-aza two-ring systems

XVI. Synthesis of 5-, 6-, and 7-carbethoxymethyl-1,2-dihydropyrrolizines and method for the isolation of 5-carbethoxymethyl-1,2-dihydropyrrolizines from mixtures with other isomers

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Abstract

Mixtures of isomeric 5-, 6-, and 7-carbethoxymethyl-1,2-dihydropyrrolizines were obtained by reaction of 1,2-dihydropyrrolizines with ethyl diazoacetate. The effect of the position of the alkyl groups in the two-membered ring on the ratio of isomers in the reaction products is demonstrated. A method for the isolation of 5-carbethoxymethyl-1,2-dihydropyrrolizines from the mixtures of isomers based on the difference in their reactivities in diazo coupling is described. The preferred conformations of the two-membered rings in the 5-carbethoxymethyl-1,2-dihydropyrrolizines are judged from the PMR spectral data.

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See [1] for communication XV.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1090–1096, August, 1977.

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Skvortsov, I.M., Kolesnikov, S.A., Samitov, Y.Y. et al. Research on 1-aza two-ring systems. Chem Heterocycl Compd 13, 877–883 (1977). https://doi.org/10.1007/BF00488915

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  • DOI: https://doi.org/10.1007/BF00488915

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