A Novel Synthesis of Quinazolines by Cyclization of 1‐(2‐Isocyanophenyl)alkylideneamines Generated by the Treatment of 2‐(1‐Azidoalkyl)phenyl Isocyanides with NaH. Issue 6 (June 2014)

• Record Type: Journal Article
• Authors: Ezaki, Kosuke; Kobayashi, Kazuhiro
• Is Part Of: Helvetica chimica acta. Volume 97:Issue 6(2014:Jun.)
• Page Start: 822
• Page End: 829
• Publication Date: 2014-06
• Subjects: Chemistry -- Periodicals; Chemistry, Analytical -- periodicals; Chimie -- Périodiques; 540
• DOI: 10.1002/hlca.201300431
• Languages: English
• ISSNs: 0018-019X

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>A new and efficient method for the synthesis of quinazolines has been developed. Thus, <italic>N</italic>‐[2‐(1‐azidoalkyl)phenyl]formamides <bold>1</bold> are dehydrated with POCl₃ to give the corresponding 2‐(1‐azidoalkyl)phenyl isocyanides <bold>2</bold>, which are then treated with NaH in DMF at 0° to give quinazolines <bold>6</bold> in satisfactory yields <italic>via</italic> cyclization of 1‐(2‐isocyanophenyl)alkylideneamine intermediates <bold>4</bold>. This methodology can be applied to the synthesis of the 7‐azaanalogs of quinazolines, <italic>i.e.</italic>, pyrido[3, 4‐<italic>d</italic>]pyrimidines <bold>9</bold>.</p> </abstract>