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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| Authors: | Kosuke Ezaki Kazuhiro Kobayashi |
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| Affiliation: | Division of Applied Chemistry, Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4‐101 Koyama‐minami, Tottori 68‐8552, Japan, (phone/fax: +81‐857‐315263) |
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| Abstract: | 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 . |
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| Keywords: | Quinazolines Alkylidene‐1‐amines Azides Isocyanides Denitrogenation |
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