A new entry to the synthesis of 2,3-disubstituted indoles
Chisato Mukai1, Yukie Takahashi
1Division of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan. cmukai@kenroku.kanazawa-u.ac.jp
Abstract:
[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.
More Related Videos
Related Concept Videos
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Directing and Steric Effects in Disubstituted Benzene Derivatives
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)
The reaction begins with an attack of the nucleophile on the carbon that holds the leaving group. This results in the delocalization of the π electrons over the ring carbons. The resonance interaction between the...


