Intramolecular cascade rearrangements of enynamine derived ketenimines: access to acyclic and cyclic amidines

Organic & Biomolecular Chemistry
Dinesh Pratapsinh ChauhanPinaki Talukdar

Abstract

Copper-catalyzed reaction of enynamines with sulfonylazides provides acyclic and cyclic amidines. Nucleophilic addition of the tethered amino group on the in situ generated ketenimine forms a six-membered cyclic zwitterionic intermediate which facilitates migration of the tethered amino group to the C5-center giving the acyclic amidine. On the other hand, migration of a substituent on the amino group to C2- and C4-centers results in the formation of cyclic amidines. Computational studies were carried out to validate the mechanism which indicates that the product distribution of the process depends on the substitutions on the enynamine backbone.

References

Jul 18, 2001·Journal of the American Chemical Society·T P Yoon, D W MacMillan
Dec 20, 2003·Organic & Biomolecular Chemistry·Mateo AlajarínMaría-Mar Ortín
Nov 17, 2005·Journal of the American Chemical Society·Seung Hwan ChoSukbok Chang
Apr 3, 2007·Angewandte Chemie·Eun Jeong YooSukbok Chang
Jul 13, 2011·Chemistry, an Asian Journal·Seok Hwan KimSukbok Chang
Jul 27, 2012·Chemical Society Reviews·Ping Lu, Yanguang Wang
Nov 16, 2013·Chemical Communications : Chem Comm·Dinesh Pratapsinh ChauhanPinaki Talukdar

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Citations

Jan 9, 2021·The Journal of Organic Chemistry·Rui-Han DaiShi-Kai Tian
Feb 19, 2021·Chemical Reviews·Jiarong ShiYang Li

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