Cobalt-Catalyzed Direct C–H Carbonylative Synthesis of Free (NH)‑Indolo[1,2‑a]quinoxalin-6(5H)‑ones

A cobalt-catalyzed direct C–H carbonylative reaction of N-(2-(1H-indol-1-yl)­phenyl)­picolinamides for the synthesis of (NH)-indolo­[1,2-a]­quinoxalin-6­(5H)-one skeletons has been developed. Using benzene-1,3,5-triyl triformate (TFBen) as the CO source and picolinamide as the traceless directing gr...

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Bibliographic Details
Published in:Organic letters 2021-01, Vol.23 (1), p.178-182
Main Authors: Gao, Qian, Lu, Jia-Ming, Yao, Lingyun, Wang, Siqi, Ying, Jun, Wu, Xiao-Feng
Format: Article
Language:English
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Summary:A cobalt-catalyzed direct C–H carbonylative reaction of N-(2-(1H-indol-1-yl)­phenyl)­picolinamides for the synthesis of (NH)-indolo­[1,2-a]­quinoxalin-6­(5H)-one skeletons has been developed. Using benzene-1,3,5-triyl triformate (TFBen) as the CO source and picolinamide as the traceless directing group, various free (NH)-indolo­[1,2-a]­quinoxalin-6­(5H)-ones were obtained in good yields (up to 88%). Additionally, a series of product derivatizations were demonstrated, and the core fragment of PARP-1 inhibitor C can be readily constructed by this protocol.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.0c03900