Switching the chemoselectivity in the amination of 4-chloroquinazolines with aminopyrazoles

Zhenlu Shen; Yiming Hong; Xiaofei He; Weimin Mo; Baoxiang Hu; Nan Sun; Xinquan Hu

doi:10.1021/ol902759k

Switching the chemoselectivity in the amination of 4-chloroquinazolines with aminopyrazoles

Org Lett. 2010 Feb 5;12(3):552-5. doi: 10.1021/ol902759k.

Authors

Zhenlu Shen¹, Yiming Hong, Xiaofei He, Weimin Mo, Baoxiang Hu, Nan Sun, Xinquan Hu

Affiliation

¹ College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310014, China. zhenlushen@zjut.edu.cn

PMID: 20043642
DOI: 10.1021/ol902759k

Abstract

The chemoselectivity in the amination of 4-chloroquinazolines with 3-amino-1H-pyrazoles was studied. Under the conditions of Pd(2)(dba)(3)/Xantphos/Na(2)CO(3), 4-chloroquinazolines underwent selective amination with the cyclic secondary amino group of 3-amino-1H-pyrazoles, whereas 4-chloroquinazolines were exclusively aminated with the primary amino group of 3-amino-1H-pyrazoles via S(N)Ar substitution in the presence of HCl.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Amination
Catalysis
Hydrocarbons, Chlorinated / chemistry*
Molecular Structure
Pyrazoles / chemistry*
Quinazolines / chemistry*

Substances

Hydrocarbons, Chlorinated
Pyrazoles
Quinazolines