Unexpected ring-expansion of 1,2-benzisoxazol-3-ones
A novel and unexpected ring-expansion reaction of 1,2-benzisoxazol-3-ones is identified. The scope of this reaction is exemplified and the proposed mechanism is also implicated in another degradation process. This reaction also represents a new method for accessing the 4H-1,3-benzoxazin-4-one skeleton.
Raw, Steven A.,O'Kearney-Mcmullan, Anne M.,Graham, Mark A.
scheme or table
p. 6775 - 6778
(2012/01/03)
A NEW "ONE POT" PREPARATION OF 2-N,N-DIALKYLAMINO-1,3-BENZOXAZINES AND NAPHTHOXAZINES FROM CORRESPONDING ORTHO HYDROXYNITRILES AND PHOSGENIMINIUM SALTS
Phosgeniminium salts 2 react easily with ortho hydroxybenzonitriles 1 and 2-hydroxy-1-naphthonitriles 6 to give 1,3-benzoxazine and naphthoxazine derivatives respectively with a very good yield.
Kokel, Bruno,Menichi, Gabriel,Hubert-Habart, Michel