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Thermal rearrangement of some 3-substituted-2,1-benzisoxazoles

โœ Scribed by Robert K. Smalley; Richard H. Smith; Hans Suschitzky

Publisher
Elsevier Science
Year
1979
Tongue
French
Weight
363 KB
Volume
20
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

3-(Phenyliminomethyl)-and 3-arylazo-2,1-benzisoxaaoles undergo thermal rearrangement to 3-phenylquinazolin-4-one and 3-aryl-1,2,3-benzotriazin-4-ones, respectively.

In a recent letter' the thermal rearrangements of some 3-(8-styryl)-2,1-benzisoxazoles (1; X=Y=CH) to 3-aryl-4-quinolones and 2-arylideneindoxyls (3; Y=CH) were discussed. As outlined in Scheme 1 loss of a proton from the dipolar structure (2; X=Y=CH) is a likely reaction path to 2-arylideneindoxyls (3), whereas quinolone formation is understandable on

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