Organic Letters
Organic Letters
5 years ago

Heteroannulation of 3-Nitroindoles and 3-Nitrobenzo[b]thiophenes: A Multicomponent Approach toward Pyrrole-Fused Heterocycles

Heteroannulation of 3-Nitroindoles and 3-Nitrobenzo[b]thiophenes: A Multicomponent Approach toward Pyrrole-Fused Heterocycles
Akhil Krishnan R, Jubi John, P. V. Santhini, E. Suresh, Sheba Ann Babu
A simple, efficient, and general multicomponent reaction involving an enolizable ketone, a primary amine, and an N-protected 3-nitroindole was developed for the synthesis of a range of functionalized pyrrolo[3,2-b]indoles. The methodology was efficaciously utilized for the “pyrroloindoliztion” of natural products, the pyrrolization of 3-nitrobenzo[b]thiophene, and the gram-scale synthesis of pyrroloindole. Furthermore, a “one-pot” approach for accessing indolo[3,2-b]indoles was realized.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01147

DOI: 10.1021/acs.orglett.7b01147

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