Acetylation of indolobenzo[b]furans, pyrrolocarbazole, pyrrolophenothiazine dioxide and pyrroloacridine under Vilsmeier reaction conditions

Abstract

The course of the Vilsmeier acetylation of new heterocyclic systems, namely, indolo[4,5-d]-, indolo[6,5-d]-, indolo[5,6-d]-, indolo[5,4-d]benzo[b]furans, 3H-pyrrolo[2,3-c]carbazole, 3H-pyrrolo[2,3-c]pheno-thiazine 11,11-dioxide, and 3H-pyrrolo[2,3-c]acridine depends on the type of fusion of the pyrrole ring. Angular heterocycles are acetylated at the β-position of the pyrrole ring, while linear heterocycles under analogues conditions give dimerization products with a substituent at the nitrogen atom of the hydrogenated part of the dimer molecule. 3H-Pyrrolo[2,3-c]phenothiazine 11,11-dioxide and 3H-pyrrolo[2,3-c]acridine are not acetylated under Vilsmeier reaction conditions.

How to Cite
Khoshtariya, T. E.; Kurkovskaya, L. N.; Suvorov, N. N. Chem. Heterocycl. Compd. 1996, 32, 1141. [Khim. Geterotsikl. Soedin. 1996, 1331.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF01169223