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

Prasenjit Sau; Amitava Rakshit; Tipu Alam; Hemant Kumar Srivastava; Bhisma K Patel

doi:10.1021/acs.orglett.9b01430

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

Org Lett. 2019 Jul 5;21(13):4966-4970. doi: 10.1021/acs.orglett.9b01430. Epub 2019 Jun 17.

Authors

Prasenjit Sau¹, Amitava Rakshit¹, Tipu Alam¹, Hemant Kumar Srivastava¹, Bhisma K Patel¹

Affiliation

¹ Department of Chemistry , Indian Institute of Technology Guwahati , North Guwahati 781039 , India.

PMID: 31247805
DOI: 10.1021/acs.orglett.9b01430

Abstract

tert-Butyl nitrite (TBN) mediated synthesis of 3-aryl-1,2,4-oxadiazol-5(4 H)-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(4 H)-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.