[4 + 3]-Cycloaddition of aza-o-quinone methides and azomethine imines to make 1,2,4-triazepines

An unprecedented formal [5+2] cyclization of N,N′‐cyclic azomethine imines with triazines has been realized, which provides a facile access to biologically important 1,2,4,6‐tetrazepine frameworks with overall high yields (up to 98% yield). This methodology is distinguished by not involving a metal catalyst, readily available starting materials, and operational simplicity, which involves the reassembly of two C−N bonds.

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Advances in [4+3]‐Annulation/Cycloaddition Reactions Leading to Homo‐ and Heterocycles with Seven‐Membered Rings

Selvaraj

Chauhan

Sandeep

et al. 2020

Chemistry An Asian Journal

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In this review, we summarize advances in [4+3] and a few other annulation/cycloaddition reactions for the construction of seven membered rings, with an emphasis on the literature subsequent to the year 2010. The type of products include the following: azepines, diazepines, benzazepinones, 1,2‐diazepinones, oxazepinones, benzothiazepines, benzodiazepinones, benzoxopinones, cyclohepta[b]indoles, benzoxazepines, azepino‐indoles, oxepines/oxazepanes, triazepines oxepinoindolones/azepinoindolones, oxadiazepines, azabicyclooctanes. Emphasis is also given to cover diverse types of annulations; possible intermediates are displayed in the illustrated schemes to aid future work.

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[4 + 3]-Cycloaddition of aza-o-quinone methides and azomethine imines to make 1,2,4-triazepines

Cited by 15 publications

References 45 publications

Tandem Phospha‐Michael Addition/N‐Acylation/ Intramolecular Wittig Reaction of aza‐o‐Quinone Methides: Approaches to 2,3‐Disubstituted Indoles

Tandem Phospha‐Michael Addition/N‐Acylation/ Intramolecular Wittig Reaction of aza‐o‐Quinone Methides: Approaches to 2,3‐Disubstituted Indoles

[5+2] Cyclization of N,N′‐Cyclic Azomethine Imines with 1,3,5‐Triazines: An Efficient Protocol for the Synthesis of Tetrazepine Derivatives

Advances in [4+3]‐Annulation/Cycloaddition Reactions Leading to Homo‐ and Heterocycles with Seven‐Membered Rings

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[4 + 3]-Cycloaddition of aza-o-quinone methides and azomethine imines to make 1,2,4-triazepines

Cited by 15 publications

References 45 publications

Tandem Phospha‐Michael Addition/N‐Acylation/ Intramolecular Wittig Reaction of aza‐o‐Quinone Methides: Approaches to 2,3‐Disubstituted Indoles

Tandem Phospha‐Michael Addition/N‐Acylation/ Intramolecular Wittig Reaction of aza‐o‐Quinone Methides: Approaches to 2,3‐Disubstituted Indoles

[5+2] Cyclization of N,N′‐Cyclic Azomethine Imines with 1,3,5‐Triazines: An Efficient Protocol for the Synthesis of Tetrazepine Derivatives

Advances in [4+3]‐Annulation/Cycloaddition Reactions Leading to Homo‐ and Heterocycles with Seven‐Membered Rings

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Product

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[4 + 3]-Cycloaddition of aza-o-quinone methides and azomethine imines to make 1,2,4-triazepines