Novel quinazoline ring synthesis by cycloaddition of N-arylketenimines with N,N-disubstituted cyanamides.
The reaction of N-aryl-substituted ketenimines with N,N-disubstituted cyanamides or (MeS)2C=N-CN under high pressure afforded 4-(N,N-disubstituted amino) or 4-(MeS)2C=N-substituted quinazoline derivatives, respectively. These products were formed by [4+2] cycloaddition between the aza-diene moieties of the N-arylsubstituted ketenimines and cyano groups. A 4-(unsubstituted amino)quinazoline derivative was synthesized by hydrolysis of the latter product.
Shimizu
Masao
M
National Institute of Advanced Industrial Science and Technology, Tsukuba Central 5, Ibaraki, Japan. m.shimizu@aist.go.jp
Oishi
Akihiro
A
Taguchi
Yoichi
Y
Gama
Yasuo
Y
Shibuya
Isao
I
D000577:Amides / Q000737:chemistry*; D007097:Imines / Q000737:chemistry*; D011799:Quinazolines / Q000138:chemical synthesis*; D013057:Spectrum Analysis
D000577:Amides; D007097:Imines; D011799:Quinazolines