Chinese Journal of Organic Chemistry >
Solvent Mediated Selective C—H Bond Iodination of Pyrrolo[1,2-a]quinoxaline
Received date: 2021-07-15
Revised date: 2021-08-20
Online published: 2021-09-03
Supported by
National Natural Science Foundation of China(21563025); National Natural Science Foundation of China(22162022)
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.
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 . DOI: 10.6023/cjoc202107033
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