4.5 Article

Lewis Acid Mediated [3+2] and [3+3] Annulations of an Azomethine Imine with Donor-Acceptor Cyclopropanes

Journal

SYNTHESIS-STUTTGART
Volume 53, Issue 16, Pages 2865-2873

Publisher

GEORG THIEME VERLAG KG
DOI: 10.1055/a-1503-8068

Keywords

pyrazolidines; [3+2] cycloaddition; [3+3] cycloaddition; azomethine imines; donor-acceptor cyclopropanes

Funding

  1. Syngenta Research & Technology Centre, Goa

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Two different Lewis acids were utilized to achieve regioselective [3+2] and [3+3] cycloaddition reactions of an azomethine imine with activated cyclopropanes, resulting in moderate yields of tetrahydropyrazolone derivatives and tricyclic tetrahydrofuran derivatives as well as high regioselectivity in forming hexahydropyridazinone derivatives.
Two different Lewis acids were used for developing [3+2] and [3+3] regioselective cycloaddition reactions of an azomethine imine with activated cyclopropanes. Scandium(III) triflate catalyzes a [3+2] cycloaddition reaction of the azomethine imine with cyclopropanes to form tetrahydropyrazolone derivatives and tricyclic tetrahydrofuran derivatives in moderate yields. Complementary to this, a novel [3+3] cycloaddition reaction of the azomethine imine with activated cyclopropanes was developed by using EtAlCl2 as a Lewis acid to form hexahydropyridazinone derivatives in high regioselectivity.

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