Reaction of 2-chloroindole-3-carbaldehyde with epihalogenohydrins. Tandem oxirane-opening—1,3-oxazole-closure process

Reaction of 2-chloroindole-3-carbaldehyde with epibromohydrin gives the expected 1-(oxiran-2-ylmethyl) derivative. However the analogous reaction with epichlorohydrin leads to the formation of the oxazolo[3,2-a]indole skeleton. Some chemical properties of this tricyclic system were investigated. Its reaction with secondary amines unexpectedly proceeds with the opening of the oxazole ring.

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