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Communication | Regular issue | Vol 2, No. 5, 1974, pp.559-563
Published online, 1st January, 1970
DOI: 10.3987/R-1974-05-0559
A Novel Formation of 1-Hydroxymethyl-4,5-dimethoxy-7H-azirino[1,2-a]indole-7a-carboxylic Acid γ-Lactone

Tetsuji Kametani,* Frank F. Ebetino, Keiichiro Fukumoto, and Albert I. Meyers

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


α-(6-Nitroveratrylidene)-γ-butyrolactone (1) rearranges to 3-(6-nitroveratryl)-2(5H)-furanone (5), and is deoxygenated to 1-hydroxymethyl-4,5-dimethoxy-7H-azirino[1,2-a]indole-7a-carboxylic acid γ-lactone (6) in triethyl phosphite at 140 - 150 °. Although frequently postulated in triethyl phosphite reductions of nitro compounds, aziridines have not, heretofore, been isolated.