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I2‑DMSO-Mediated N–H/α-C(sp3)–H Difunctionalization of Tetrahydroisoquinoline: Formal [2 + 2 + 1] Annulation for the Construction of Pyrrolo[2,1‑a]isoquinoline Derivatives

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journal contribution
posted on 08.04.2022, 18:04 by Shi-Yi Zhuang, Yong-Xing Tang, Jin-Yi Liu, Xiang-Long Chen, Jin-Tian Ma, Yan-Dong Wu, Kai-Lu Zheng, An-Xin Wu
An I2-DMSO-mediated cascade reaction using methyl ketones and 1,2,3,4-tetrahydroisoquinolines (THIQs) as commercially available substrates has been developed for the construction of pyrrolo­[2,1-a]­isoquinoline derivatives. This metal-free process involves N–H/α-C­(sp3)–H difunctionalization of THIQ. Two C–C bonds and one C–N bond are formed in one pot under mild conditions. Besides, a quaternary carbon center has been constructed in this transformation efficiently.