Journal of Organic Chemistry
Journal of Organic Chemistry
5 years ago

NIS Mediated Cross-Coupling of C(sp2)–H and N–H Bonds: A Transition-Metal-Free Approach toward Indolo[1,2-a]quinazolinones

NIS Mediated Cross-Coupling of C(sp2)–H and N–H Bonds: A Transition-Metal-Free Approach toward Indolo[1,2-a]quinazolinones
Govindasamy Sekar, Sindhura Badigenchala
A metal- and base-free protocol for intramolecular cross-coupling of C(sp2)–H and N–H bonds using N-iodosuccinimide (NIS) has been demonstrated. This environmentally benign approach furnishes a series of substituted indolo[1,2-a]quinazolinones from the suitably fabricated indoles via C–N bond forming cyclization in 28–82% yield. A plausible mechanism is proposed for this cyclization based on the results of a control experiment. This methodology requires no additional metal catalyst, oxidant, or base. Furthermore, the synthetic utility of the protocol is demonstrated by performing a gram scale reaction.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b01080

DOI: 10.1021/acs.joc.7b01080

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