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AlMe 3 ‐Mediated Regio‐ and Chemoselective Reactions of Indole with Carbamoyl Electrophiles
Author(s) -
Velavan A.,
Sumathi S.,
Balasubramanian K. K.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300085
Subject(s) - indole test , chemistry , electrophile , chemoselectivity , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis
Herein, we report the regio‐ and chemoselective reactions of indole with carbamoyl electrophiles in presence of AlMe 3 . Indole‐3‐carboxamide was prepared in one‐step from a reaction of indole with tertiary carbamoylimidazole in the presence AlMe 3 . Under conditions for the formation of an aluminium ate complex, the reaction was diverted to the indole nitrogen. Secondary carbamoyl electrophiles in the presence of AlMe 3 regiospecifically yielded trisubstituted ureas. The regiospecificity and chemoselectivity of the indole nitrogen towards ester and tertiary carbamoylimidazole functionalities were also studied.