Title

AlMe<sub>3</sub>-Mediated Regio- and Chemoselective Reactions of Indole with Carbamoyl Electrophiles.

Authors

Velavan, A.; Sumathi, S.; Balasubramanian, K. K.

Abstract

Herein, we report the regio- and chemoselective reactions of indole with carbamoyl electrophiles in presence of AlMe3. Indole-3-carboxamide was prepared in one-step from a reaction of indole with tertiary carbamoylimidazole in the presence AlMe3. 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 AlMe3 regiospecifically yielded trisubstituted ureas. The regiospecificity and chemoselectivity of the indole nitrogen towards ester and tertiary carbamoylimidazole functionalities were also studied.

Publication

European Journal of Organic Chemistry, 2013, Vol 2013, Issue 15, p3148

ISSN

1434-193X

Publication type

Academic Journal

DOI

10.1002/ejoc.201300085