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Simple synthesis of indoles and of corresponding 3 2h indolone derivatives monosubstituted at the benzene ring as synthetic precursors of natural compounds



Simple synthesis of indoles and of corresponding 3 2h indolone derivatives monosubstituted at the benzene ring as synthetic precursors of natural compounds



Liebigs Annalen der Chemie (9): 765-770



Application of a specific BCl3-catalyzed ortho-chloroacetylation of the monosubstituted primary anilines 2a-e with chloroacetonitrile, as a variant of the Houben-Hoesch reaction, leads to the corresponding 2-amino-.alpha.-chloroacetophenones 3a-g. These may be reduced and cyclized to yield the indoles 4a-g or, after acylation to 5a-g and 7a,b converted by base-catalyzed dehydrochlorination into the 1-acyl-3(2H)-indolones 6a-g and 8a, b.

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