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Communication | Regular issue | Vol 6, No. 7, 1977, pp.887-893
Published online, 1st January, 1970
DOI: 10.3987/R-1977-07-0887
A Novel Method for Acetylization of Formyl Group at the C3-Position of 2,3-Dihydro-1H-pyrrolo[1,2-a]indole Skeleton

Tetsuji Kametani,* Yoshio Kigawa, Kimio Takahashi, Hideo Nemoto, and Keiichiro Fukumoto

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan

Abstract

Reaction of 2,3-dihydro-7-methoxy-6-methyl-1H-pyrrolo[1,2-a]indole-9-carboxaldehydes 2, 3, 4, 5, and 6 with thiolacetic acid in the presence of 6N sulfuric acid at room temperature gave 2,3-dihydro-7-methoxy-6-methyl-9-dithiolacetylmethyl-1H-pyrrolo[1, 2-a]indoles 12, 13, 14, 15, and 16, respectively. The same reaction of the compound 2 at 0 ° afforded 1-acetoxy-2,3-dihydro-7-methoxy-6-methyl-8-nitro-9-dithiolacetylmethyl-1H-pyrrolo[1,2-a]indole (11). Successive treatment of the compound 11 with anhydrous methanol in the presence of sodium methoxide gave 2,3-dihydro-1-hydroxy-7-methoxy-9-dimethoxymethyl-6-methyl-8-nitro-18-pyrrolo[1,2-a]indole (17).