Synthesis of Trisubstituted Oxazoles via Aryne Induced [2,3] Sigmatropic Rearrangement–Annulation Cascade

Gaykar, Rahul N. ; Deswal, Shiksha ; Guin, Avishek ; Bhattacharjee, Subrata ; Biju, Akkattu T. (2022) Synthesis of Trisubstituted Oxazoles via Aryne Induced [2,3] Sigmatropic Rearrangement–Annulation Cascade Organic Letters, 24 (23). pp. 4145-4150. ISSN 1523-7060

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Official URL: http://doi.org/10.1021/acs.orglett.2c01379

Related URL: http://dx.doi.org/10.1021/acs.orglett.2c01379

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.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society
ID Code:128576
Deposited On:03 Nov 2022 06:38
Last Modified:11 Nov 2022 06:33

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