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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 |
Appears in Collections: | JOURNAL ARTICLES |
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