Synthesis of C(2)Halomethyl Substituted Derivatives of 2,3-Dihydro-1,3-benzoxaz-4-ones

Abstract

In the pursuit of biologically active compounds we required as a key intermediate 2,3-dihydro- 1,3-benzoxaz-bones having a halomethylene moiety at C(2), i.e. 3 (R₂ = H or alkyl, R₃ = CH₂X). The standard procedure for the preparation of this class of compounds is the condensation of salicylamide derivatives 1 with the proper aldehyde^1-5 and ketone^5,6. Usually, hydrochloric acid or sulphuric acid is used as catalyst and the water formed is cocornmittently removed using a dehydrating agent or by azeotropic destillation⁷. These procedures did not serve our purpose as the required α-substituted aldehyde or ketone as such is unstable under the conditions employed. Here we report that employment of acetals and ketals 2 affords the desired compound 3; yields are appreciable when the proper reaction conditions are used.