Please use this identifier to cite or link to this item: http://dr.iiserpune.ac.in:8080/xmlui/handle/123456789/3243
Title: Intramolecular cascade rearrangements of enynamine derived ketenimines: access to acyclic and cyclic amidines
Authors: Chauhan, Dinesh Pratapsinh
Varma, Sreejith Jayasree
GUDEM, MAHESH
Panigrahi, Nihar
Singh, Khushboo
HAZRA, ANIRBAN
TALUKDAR, PINAKI
Dept. of Chemistry
Keywords: Intramolecular cascade
Enynamine
Cyclic amidines
Preliminary investigation
Quantum chemical calculations
2017
Issue Date: May-2017
Publisher: Royal Society of Chemistry
Citation: Organic & Biomolecular Chemistry, 15(22), 4822-4830.
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
URI: http://dr.iiserpune.ac.in:8080/xmlui/handle/123456789/3243
https://doi.org/10.1039/C7OB00499K
ISSN: 1477-0520
1477-0539
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