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S 8 ‐Mediated Cyclization of 2‐Aminophenols/thiophenols with Arylmethyl Chloride: Approach to Benzoxazoles and Benzothiazoles
Author(s) -
Gan Haifeng,
Miao Dazhuang,
Pan Qiang,
Hu Renhe,
Li Xiaotong,
Han Shiqing
Publication year - 2016
Publication title -
chemistry – an asian journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.18
H-Index - 106
eISSN - 1861-471X
pISSN - 1861-4728
DOI - 10.1002/asia.201600355
Subject(s) - oxidizing agent , sulfur , chemistry , combinatorial chemistry , metal , functional group , crystal structure , medicinal chemistry , organic chemistry , polymer
A metal‐free approach to benzazoles from arylmethyl chlorides and 2‐mercaptan/2‐hydroxyanilines using elemental sulfur as a traceless oxidizing agent has been developed. The reactions proceeded in good to excellent yields, exhibiting good functional groups tolerance and gram‐scale ability. A key mechanistic investigation indicated that the key intermediate trisulfide 6 , which was characterized by NMR, HRMS and crystal X‐ray crystallography, was separated in the reaction prior to the formation of the product.