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

Raghuramaiah Mandadapu; Amol Satish Dehade; Shrikant Abhiman Shete; Mark Montgomery; Vikas Sikervar; Ravindra Sonawane

doi:10.1055/a-1503-8068

Synthesis, Table of Contents

Synthesis 2021; 53(16): 2865-2873
DOI: 10.1055/a-1503-8068

paper

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

Raghuramaiah Mandadapu

^aSyngenta Biosciences Pvt. Ltd. Santa Monica Works, Corlim, Ilhas, Goa, 403110, India

^bDepartment of Chemistry, Mangalore University, Mangalagangothri, 576119, Karnataka, India

,

Amol Satish Dehade

^aSyngenta Biosciences Pvt. Ltd. Santa Monica Works, Corlim, Ilhas, Goa, 403110, India

,

Shrikant Abhiman Shete

^aSyngenta Biosciences Pvt. Ltd. Santa Monica Works, Corlim, Ilhas, Goa, 403110, India

,

Mark Montgomery

^cSyngenta, Jealott’s Hill International Research Centre, Bracknell, Berkshire RG42 6EY, UK

,

Vikas Sikervar ∗

^aSyngenta Biosciences Pvt. Ltd. Santa Monica Works, Corlim, Ilhas, Goa, 403110, India

,

Ravindra Sonawane∗

^aSyngenta Biosciences Pvt. Ltd. Santa Monica Works, Corlim, Ilhas, Goa, 403110, India

› Author Affiliations

Abstract

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Abstract

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.

Key words

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

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References

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