Molecular iodine-mediated formal [2+1+1+1] cycloaddition access to pyrrolo[2,1-a]isoquinolines with DMSO as the methylene source

Kailu Zheng; Shiyi Zhuang; Wenming Shu; Yandong Wu; Chuluo Yang; Anxin Wu

doi:10.1039/C8CC06908E

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Molecular iodine-mediated formal [2+1+1+1] cycloaddition access to pyrrolo[2,1-a]isoquinolines with DMSO as the methylene source†

Kailu Zheng,‡^ab Shiyi Zhuang,‡^a Wenming Shu,^a Yandong Wu,^a Chuluo Yang

*^b and Anxin Wu

*^a

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* Corresponding authors

^a Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, P. R. China
E-mail: chwuax@mail.ccnu.edu.cn

^b Department of Chemistry and Hubei Key Lab on Organic and Polymeric Optoelectronic Materials, Wuhan University, Wuhan, P. R. China

Abstract

A molecular iodine-mediated formal [2+1+1+1] cycloaddition for the efficient synthesis of pyrrolo[2,1-a]isoquinolines from acetophenones, 1,2,3,4-tetrahydroisoquinoline (THIQ) and DMSO has been developed. Mechanistic studies revealed that DMSO served as the methylene source, and this novel protocol involves intermolecular cycloaddition of two in situ generated intermediates that enable efficient formation of one C–N bond and three C–C bonds via multiple sequential C–H functionalizations.

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DOI: https://doi.org/10.1039/C8CC06908E
Article type: Communication
Submitted: 25 Aug 2018
Accepted: 25 Sep 2018
First published: 01 Oct 2018

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Chem. Commun., 2018,54, 11897-11900

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Molecular iodine-mediated formal [2+1+1+1] cycloaddition access to pyrrolo[2,1-a]isoquinolines with DMSO as the methylene source

K. Zheng, S. Zhuang, W. Shu, Y. Wu, C. Yang and A. Wu, Chem. Commun., 2018, 54, 11897 DOI: 10.1039/C8CC06908E

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Chemical Communications

Molecular iodine-mediated formal [2+1+1+1] cycloaddition access to pyrrolo[2,1-a]isoquinolines with DMSO as the methylene source†

Abstract

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Molecular iodine-mediated formal [2+1+1+1] cycloaddition access to pyrrolo[2,1-a]isoquinolines with DMSO as the methylene source

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