A new entry to the synthesis of 2,3-disubstituted indoles.
[reaction: see text] The Stille coupling of N-acyl-2-iodoanilines with the 1-(tributylstannyl)-1-substituted allenes affected the successive one-step formation of the 2-methyl-3-substituted indoles. Alternatively, the other type of 2-alkyl-3-substituted indoles could be synthesized in a one-pot operation, which consists of the Stille coupling reaction with the 1-(tributylstannyl)-1,3-disubstituted allenes, followed by TBAF treatment. This procedure could be applied to the synthesis of indomethacin.
Mukai
Chisato
C
Division of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan. cmukai@kenroku.kanazawa-u.ac.jp
Takahashi
Yukie
Y
D000475:Alkenes / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques; D026121:Indole Alkaloids / Q000138:chemical synthesis; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D007213:Indomethacin / Q000138:chemical synthesis; D015394:Molecular Structure
D000475:Alkenes; D026121:Indole Alkaloids; D007211:Indoles; D007213:Indomethacin