Lewis Acid Mediated [3+2] and [3+3] Annulations of an Azomethine Imine with Donor–Acceptor Cyclopropanes-Reference-Cited by-同舟云学术

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

Published:2021-05-10 Issue:16 Volume:53 Page:2865-2873
ISSN:0039-7881
Container-title:Synthesis
language:en
Short-container-title:Synthesis

Author:

Sikervar Vikas¹^ORCID,Sonawane Ravindra¹,Mandadapu Raghuramaiah¹²,Dehade Amol Satish¹,Shete Shrikant Abhiman¹,Montgomery Mark³

Affiliation:

1. Syngenta Biosciences Pvt. Ltd. Santa Monica Works

2. Department of Chemistry, Mangalore University

3. Syngenta, Jealott’s Hill International Research Centre

Abstract

AbstractTwo 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.

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Catalysis

Link

http://www.thieme-connect.de/products/ejournals/pdf/10.1055/a-1503-8068.pdf

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