Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

Catalyst-free Synthesis of 6-Hydroxy Indoles via the Condensation of Carboxymethyl Cyclohexadienones and Amines

Catalyst-free Synthesis of 6-Hydroxy Indoles via the Condensation of Carboxymethyl Cyclohexadienones and Amines
Komalkant Adlak, Prasanta Ghorai, Reddy Rajasekhar Reddy
An efficient catalyst-free synthesis of 6-hydroxy indoles from carboxymethyl cyclohexadienones and primary amines has been developed. The aza-Michael addition of the in situ formed enamine, generated through the condensation of carboxymethyl unit of the substrates with an external amine, to cyclohexadienone moiety followed by rearomatization reaction to provide such indoles. Anilines, aliphatic amines, α-chiral aliphatic amines, or even ammonia were used as amine counterpart. Some of the cyclohexadienones gave 6-amino indoles instead of 6-hydroxy indoles using the Re2O7 catalyst. Various post methodological transformations were performed to explore the synthetic utility of the synthesized hydroxy indoles.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01136

DOI: 10.1021/acs.joc.7b01136

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