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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
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 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 .