Issue 27, 2022
From the journal:

Chemical Communications

Nitrative bicyclization of 1,7-diynes for accessing skeletally diverse tricyclic pyrroles†

Lu Wang,a   Yin Zhang,a   An-Qi Miao,a   Tian-Shu Zhang,*b   Xiang Wang,c   Wen-Juan Hao, ORCID logo *a   Shu-Jiang Tu ORCID logo a  and  Bo Jiang ORCID logo *a  

* Corresponding authors

a School of Chemistry & Materials Science, Jiangsu Normal University, Xuzhou, P. R. China
E-mail: wjhao@jsnu.edu.cn, jiangchem@jsnu.edu.cn

b School of Materials and Chemical Engineering, Xuzhou University of Technology, Xuzhou 221018, P. R. China
E-mail: zts11975@xzit.edu.cn

c School of Chemistry and Chemical Engineering, Huaiyin Normal University, Huaian 223300, People's Republic of China

Abstract

A novel metal-free nitrative bicyclization of 1,7-diynes with tBuONO in the presence of H2O is reported, producing three types of skeletally diverse tricyclic pyrroles, namely pyrrolo[3,4-c]quinolines, chromeno[3,4-c]pyrroles and benzo[e]isoindoles, with moderate to good yields by simply tuning the linkers of the 1,7-diynes. This domino protocol demonstrates remarkable compatibility regarding 1,7-diynes with different linkers, such as nitrogen and oxygen atoms and a hydroxymethyl group, and tBuONO plays dual roles as a nitro precursor as well as a nitrogen atom source.

Graphical abstract: Nitrative bicyclization of 1,7-diynes for accessing skeletally diverse tricyclic pyrroles

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/D2CC00206J
Article type
Communication
Submitted
12 Jan 2022
Accepted
07 Mar 2022
First published
07 Mar 2022

Chem. Commun., 2022,58, 4376-4379

Permissions

Request permissions

Nitrative bicyclization of 1,7-diynes for accessing skeletally diverse tricyclic pyrroles

L. Wang, Y. Zhang, A. Miao, T. Zhang, X. Wang, W. Hao, S. Tu and B. Jiang, Chem. Commun., 2022, 58, 4376 DOI: 10.1039/D2CC00206J

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