tert-Butyl Nitrite Mediated Synthesis of 1,2,4-Oxadiazol-5(4H)-ones from Terminal Aryl Alkenes

Sau, Prasenjit ; Rakshit, Amitava ; Alam, Tipu ; Srivastava, Hemant Kumar ; Patel, Bhisma K. (2019) tert-Butyl Nitrite Mediated Synthesis of 1,2,4-Oxadiazol-5(4H)-ones from Terminal Aryl Alkenes Organic Letters, 21 (13). pp. 4966-4970. ISSN 1523-7060

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Official URL: http://doi.org/10.1021/acs.orglett.9b01430

Related URL: http://dx.doi.org/10.1021/acs.orglett.9b01430

Abstract

tert-Butyl nitrite (TBN) mediated synthesis of 3-aryl-1,2,4-oxadiazol-5(4H)-ones has been accomplished using terminal aryl alkenes via a biradical reaction intermediate. Three consecutive sp2 C–H bond functionalizations of styrenes afforded 3-phenyl-1,2,4-oxadiazol-5(4H)-ones via the formation of new C═N, C═O, C–O, and two C–N bonds. Both of the N atoms originate from TBN, while the carbonyl oxygen is from the water (moisture) the other oxygen from the N═O part of the TBN.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:124207
Deposited On:08 Nov 2021 11:28
Last Modified:08 Nov 2021 11:28

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