Solvent Mediated Selective C—H Bond Iodination of Pyrrolo[1,2-a]quinoxaline

doi:10.6023/cjoc202107033

Abstract

A solvent mediated regioselective C—H iodination of pyrrolo[1,2-a]quinoxaline with N-iodo-succininide (NIS) has been developed. 1-Iodopyrrolo[1,2-a]quinoxalines and 3-iodopyrrolo[1,2-a]quinoxalines could be selectively synthesized by using CHCl₃ and N,N-dimethylformamide (DMF) as solvents, respectively. Furthermore, 1,3-dibromopyrroloquinoxalines were obtained as the main products by the bromination of pyrrolo[1,2-a]quinoxaline with N-bromo-succinimide (NBS). The method features simple and mild reaction conditions, good regioselectivity, broad substrate scope, and gram-scale synthesis. In addition, the further transformation of halogenated pyrrolo[1,2-a]quinoxaline products has also been investigated through palladium and iodine catalyzed C—X (X=C, S) bond formation reactions.

Key words: solvent-mediated, regioselectivity, pyrrolo[1,2-a]quinoxaline, C—H bond iodination

Cite this article

Yali Liu, Zhen Yang, Yang Li, Yan Liu, Ping Liu. Solvent Mediated Selective C—H Bond Iodination of Pyrrolo[1,2-a]quinoxaline[J]. Chinese Journal of Organic Chemistry, 2021, 41(12): 4789-4797.

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溶剂介导吡咯并[1,2-a]喹喔啉选择性C—H键碘代