Synthesis of Trisubstituted Oxazoles via Aryne Induced 2,3 Sigmatropic Rearrangement-Annulation Cascade

Gaykar, RN and Deswal, S and Guin, A and Bhattacharjee, S and Biju, AT (2022) Synthesis of Trisubstituted Oxazoles via Aryne Induced 2,3 Sigmatropic Rearrangement-Annulation Cascade. In: Organic Letters, 24 (23). pp. 4145-4150.

PDF org_let_24-23_4145-4150_2022.pdf - Published Version Restricted to Registered users only Download (1MB) | Request a copy

Abstract

A transition-metal-free, 2,3 sigmatropic rearrangement-annulation cascade of 2-substituted thio/amino acetonitriles with arynes allowing the synthesis of 2,4,5-trisubstituted oxazoles under mild conditions has been demonstrated. The key sulfur/nitrogen ylides were generated by the initial S/N arylation followed by proton transfer, which was followed by the selective 2,3 sigmatropic rearrangement involving the -CN moiety and a subsequent annulation to afford the desired products in reasonable yields. © 2022 American Chemical Society. All rights reserved.

Item Type:	Journal Article
Publication:	Organic Letters
Publisher:	American Chemical Society
Additional Information:	The copyright for this article belongs to the American Chemical Society.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	21 Sep 2022 09:50
Last Modified:	21 Sep 2022 09:50
URI:	https://eprints.iisc.ac.in/id/eprint/76700

Actions (login required)

View Item