Switching the chemoselectivity in the amination of 4-chloroquinazolines with aminopyrazoles.
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.
Shen
Zhenlu
Z
College of Chemical Engineering and Materials Science, Zhejiang University of Technology, Hangzhou 310014, China. zhenlushen@zjut.edu.cn
Hong
Yiming
Y
He
Xiaofei
X
Mo
Weimin
W
Hu
Baoxiang
B
Sun
Nan
N
Hu
Xinquan
X
D000586:Amination; D002384:Catalysis; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D015394:Molecular Structure; D011720:Pyrazoles / Q000737:chemistry*; D011799:Quinazolines / Q000737:chemistry*
D006843:Hydrocarbons, Chlorinated; D011720:Pyrazoles; D011799:Quinazolines