Selenium-Catalyzed Oxidative C–H Amination of (E)‑3-(Arylamino)-2-styrylquinazolin-4(3H)‑ones: A Metal-Free Synthesis of 1,2-Diarylpyrazolo[5,1‑b]quinazolin-9(1H)‑ones

A novel metal-free catalysis protocol for the synthesis of 1,2-diarylpyrazolo­[5,1-b]­quinazolin-9­(1H)-ones via intramolecular oxidative C–H amination of (E)-3-(arylamino)-2-styrylquinazolin-4­(3H)-ones has been developed in moderate to good yield. The method shows good functional group tolerance....

Full description

Saved in:
Bibliographic Details
Published in:Journal of organic chemistry 2019-03, Vol.84 (5), p.2798-2807
Main Authors: Zhang, Yetong, Shao, Yinlin, Gong, Julin, Zhu, Jianghe, Cheng, Tianxing, Chen, Jiuxi
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:A novel metal-free catalysis protocol for the synthesis of 1,2-diarylpyrazolo­[5,1-b]­quinazolin-9­(1H)-ones via intramolecular oxidative C–H amination of (E)-3-(arylamino)-2-styrylquinazolin-4­(3H)-ones has been developed in moderate to good yield. The method shows good functional group tolerance. The presented approach offers a new synthetic pathway toward the core structures of 2,3-fused quinazolinones. Moreover, the present synthetic route can be readily scaled up to gram quantity without difficulty. A possible mechanism involves a seleniranium ion followed by three-membered ring opening to form the C–N bond.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.8b03179