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

Prasenjit Sau, Amitava Rakshit, Tipu Alam, Hemant Kumar Srivastava*, Bhisma K. Patel*

*Department of Chemistry, Indian Institute of Technology Guwahati, North Guwahati 781039, India, Email: hemantsiitg.ac.in, pateliitg.ac.in

P. Sau, A. Rakshit, T. Alam, H. J. Srivastava, B. K. Patel, Org. Lett., 2019, 21, 4966-4970.

DOI: 10.1021/acs.orglett.9b01430

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Abstract

The reaction of tert-Butyl nitrite with terminal aryl alkenes provides 3-aryl-1,2,4-oxadiazol-5(4H)-ones via a biradical reaction intermediate. Both of the nitrogen atoms and one oxygen originate from TBN, while the carbonyl oxygen is from moisture.

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Key Words

N-heterocyles

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ID: J54-Y2019