3188-31-6Relevant academic research and scientific papers
Studies on the Synthesis of Heterocyclic Compounds. Part 832. A Simple and Efficient Synthesis of Apomitomycin Derivatives; a Potential Intermediate for Mitomycin Synthesis
Kametani, Tetsuji,Kigawa, Yoshio,Nemoto, Hideo,Ihara, Masataka,Fukumoto, Keiichiro
, p. 1607 - 1613 (1980)
Condensation of pyrrolidine-2-thione (21) with methyl α-bromo-(2-bromo-4,5-dimethoxyphenyl)acetate (15) gave methyl (Z)-α-(2-bromo-4,5-dimethoxyphenyl)-α-pyrrolidin-2-ylideneacetate (25) in high yield.Several other methyl (Z)-α-aryl-α-acetates (26)-(31) were also synthesised in good yields from reaction of the corresponding phenylacetates (15), (12), and (13) with trans-3-acetoxy-4-(N-ethoxycarbonyl-N-methylamino)pyrrolidine-2-thione (20).Treatment of compounds (25)-(31) with sodium hydride and copper(I) bromide in dimethylformamide afforded methyl 2,3-dihydro-6,7-dimethoxy-1H-pyrroloindole-9-carboxylate (34) and the methyl (+/-)-trans-1-acetoxy-2-(N-ethoxycarbonyl-N-methylamino)-2,3-dihydro-1H-pyrroloindole-9-carboxylates (35)-(37) in good yields.Methyl (+/-)-trans-1-acethoxy-2-(N-ethoxycarbonyl-N-methylamino)-2,3-dihydro-7-methoxy-6-methyl-1H-pyrroloindole-9-carboxylate (36) was converted into the 5,8-quinone (3), via the 8-nitro-compound (38).
