Synthesis of New Highly Substituted 1,3-Dihydroazepin-2-ones Starting from 2-Siloxycyclopropanecarboxylates

Gesine Böttcher; Hans-Ulrich Reissig

doi:10.1055/s-2000-6594

Synlett 2000; 2000(5): 0725-0727
DOI: 10.1055/s-2000-6594

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Synthesis of New Highly Substituted 1,3-Dihydroazepin-2-ones Starting from 2-Siloxycyclopropanecarboxylates

Gesine Böttcher^* , Hans-Ulrich Reissig

^*Institut für Organische Chemie, Technische Universität Dresden, 01062 Dresden, Germany; Fax + 49(0)30/838-55367; E-mail: Hans.Reissig@chemie.fu-berlin.de

Abstract

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2-Siloxysubstituted 2-alkenylcyclopropanecarboxylic acids 6a-e were converted into the corresponding carbonylazides by treatment with diphenyl phosphorazidate/triethylamine. These intermediates underwent smooth Curtius rearrangement followed by [3,3]-sigmatropic reaction to finally provide azepin-2-one derivatives 8a - d and/or azepin-2,5-diones 9d and 10e in moderate to good overall yield. Cyclopropanecarboxylic acids 11a - c lacking the siloxy group provided azepin-2-ones 12a - c with reasonable efficiency.

vinyl cyclopropanes - carbonylazides - [3,3]-sigmatropic rearrangements - azepinones

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