A Novel Synthesis of Quinazolines by Cyclization of 1‐(2‐Isocyanophenyl)alkylideneamines Generated by the Treatment of 2‐(1‐Azidoalkyl)phenyl Isocyanides with NaH | Zendy

Ezaki Kosuke | Zendy; Kobayashi Kazuhiro | Zendy

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A Novel Synthesis of Quinazolines by Cyclization of 1‐(2‐Isocyanophenyl)alkylideneamines Generated by the Treatment of 2‐(1‐Azidoalkyl)phenyl Isocyanides with NaH

Author(s) -

Ezaki Kosuke,

Kobayashi Kazuhiro

Publication year - 2014

Publication title -

helvetica chimica acta

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.74

H-Index - 82

eISSN - 1522-2675

pISSN - 0018-019X

DOI - 10.1002/hlca.201300431

Subject(s) - chemistry , formamides , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry , formamide

A new and efficient method for the synthesis of quinazolines has been developed. Thus, N ‐[2‐(1‐azidoalkyl)phenyl]formamides 1 are dehydrated with POCl 3 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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