- A novel synthesis of quinazolines by cyclization of 1-(2-isocyanophenyl) alkylideneamines generated by the treatment of 2-(1-azidoalkyl)phenyl isocyanides with NaH
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A new and efficient method for the synthesis of quinazolines has been developed. Thus, N-[2-(1-azidoalkyl)phenyl]formamides 1 are dehydrated with POCl3 to give the corresponding 2-(1-azidoalkyl)phenyl isocyanides 2, which are then treated with NaH in DMF at 0° to give quinazolines 6 in satisfactory yields via cyclization of 1-(2-isocyanophenyl)alkylideneamine intermediates 4. This methodology can be applied to the synthesis of the 7-azaanalogs of quinazolines, i.e., pyrido[3,4-d]pyrimidines 9. Copyright
- Ezaki, Kosuke,Kobayashi, Kazuhiro
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p. 822 - 829
(2014/07/07)
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- Palladium complex-catalyzed intermolecular reductive N-heterocyclization: novel synthesis of quinazoline derivatives from 2-nitrobenzaldehyde or 2-nitrophenyl ketones with formamide
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A combination of the palladium complex PdCl2(PPh3)2 with MoCl5 shows a high catalytic activity for the intermolecular reductive N-heterocyclization of 2-nitrobenzaldehyde or 2-nitrophenyl ketones with formamide to give the corresponding quinazoline derivatives in moderate yields.For example, in the reaction of 2-nitrobenzaldehyde with formamide, quinazoline was obtained in 46percent yield.We assume that the present reaction proceeds via an active nitrene intermediate which could be generated by selective deoxygenation of nitro group by carbon monoxide.Keywords: Palladium; Molybdenum; Carbon monoxide; Nitrene; Reductive N-heterocyclization
- Akazome, Motohiro,Yamamoto, Jun,Kondo, Teruyuki,Watanabe, Yoshihisa
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p. 229 - 234
(2007/10/02)
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