Issue 84, 2018

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

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.

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

Supplementary files

Article information

Article type
Communication
Submitted
25 Aug 2018
Accepted
25 Sep 2018
First published
01 Oct 2018

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

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements