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Short Paper | Regular issue | Vol 98, No. 12, 2019, pp.1755-1768
Published online, 6th January, 2020
DOI: 10.3987/COM-19-14190
Synthetic Strategy to New Terphenyl-Type Bis-Pyrrole Arenes Starting from Highly Electron-Deficient 4-Nitroanilines with 1,4-Diketones

Hyejeong Lee, Seolhee Bae, Eungyung Kim, Jihye Park, and Byeong Hyo Kim*

*Department of Chemistry, Kwangwoon University, 447-1, Wolgye-Dong Nowon-ku, Seoul, 139-701, Korea

Abstract

A new synthetic method for converting highly electron-deficient 4-nitroanilines into terphenyl-type bis-pyrrole arene derivatives has been developed, which is not easy to accomplish using conventional methods because of their poor reactivity. This process involves an indium-mediated reductive cyclization reaction of highly electron-deficient 2,6-disubstituted nitroanilines in the presence of a 1,4-diketone to form 2,6-disubstituted 4-(1H-pyrrole-1-yl)anilines followed by cyclization with another 1,4-diketone to give the target bis-pyrrole arene products in moderate to high yield.