Selective Synthesis of Bromo-substituted 2H-Pyrroles and 3H-Pyrroles via Three-Component Cascade Annulation of 1,3-Enynes, NBS and TMSN3

Zhen Zhang; Qingting Song; Fan Qin; Han Yue; Xiaoyu Xie; Lei Wang; Tao Miao

doi:10.1002/cjoc.202401260

Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (10) : 1155 -1160. DOI: 10.1002/cjoc.202401260

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Selective Synthesis of Bromo-substituted 2H-Pyrroles and 3H-Pyrroles via Three-Component Cascade Annulation of 1,3-Enynes, NBS and TMSN₃

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Abstract

A novel and efficient method for selective synthesis of bromo-substituted 2H-pyrroles and 3H-pyrroles has been achieved from 1,3-enynes, NBS and TMSN₃via H₂O-promoted cyclization reactions or TFA-catalyzed cyclization/2,3-shift reactions, providing a range of structurally diverse products in moderate to good yields under mild conditions.

Keywords

2H-Pyrroles / 3H-Pyrroles / 1,3-Enynes / H₂O-promoted / TFA-catalyzed / Cyclization

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Zhen Zhang, Qingting Song, Fan Qin, Han Yue, Xiaoyu Xie, Lei Wang, Tao Miao. Selective Synthesis of Bromo-substituted 2H-Pyrroles and 3H-Pyrroles via Three-Component Cascade Annulation of 1,3-Enynes, NBS and TMSN₃. Chinese Journal of Chemistry, 2025, 43(10): 1155-1160 DOI:10.1002/cjoc.202401260