Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 15, Pages 3148-3157Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201300085
Keywords
Synthetic methods; Acylation; Regioselectivity; Chemoselectivity; Nitrogen heterocycles; Lewis acids; Aluminum
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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.
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