Tetrahedron p. 7277 - 7286 (1995)
Update date:2022-07-30
Topics:
Makosza, Mieczyslaw
Stalewski, Jacek
5- and 6-nitrobenzoxazoles 3 and 4 react with nucleophiles exclusively at C-2, giving ring opening products. If position 2- is blocked with phenyl substituent the reaction takes place in the carbocyclic ring affording the VNS products. 2-Methylthio-5-nitrobenzoxazole 7 and its 6-nitro isomer 8 give products which result from addition of a nucleophile to the carbocyclic ring (VNS) as well as to the heterocyclic ring (S(N)Ar and ring cleavage). 2-Methylthiobenzoxazoles can be readily converted to the corresponding benzoxazolones via oxidative hydrolysis.
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