CSIR – National Institute for Interdisciplinary Science and Technology (NIIST)

Council of Scientific & Industrial Research (CSIR), Govt.Of India Thiruvananthapuram.

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

P. V. Santhini, Sheba Ann Babu, Akhil Krishnan R., E. Suresh, and Jubi John*

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.

Org. Lett. 2017, 19, 2458–2461.

Full Text Link: http://dx.doi.org/10.1021/acs.orglett.7b01147