title: One-pot synthesis of 2-substituted 4H-3,1-benzoxazin-4-one derivatives under mild conditions using iminium cation from cyanuric chloride/dimethylformamide as a cyclizing agent.
abstract: BACKGROUND
  The derivatives of 2-substituted 4H-3,1-benzoxazin-4-one belong to a significant category of heterocyclic compounds, which have shown a wide spectrum of medical and industrial applications.
  
  
  RESULTS
  A new and effective one-pot method for the synthesis of 2-substituted 4H-3,1-benzoxazin-4-one derivatives is described in this paper. By using the iminium cation from a mixture of cyanuric chloride and dimethylformamide as a cyclizing agent, a series of 2-substituted 4H-3,1-benzoxazin-4-one derivatives was synthesized in high yield under mild conditions and simple workup.
  
  
  CONCLUSIONS
  The iminium cation from a mixture of cyanuric chloride and N,N-dimethylformamide is an effective cyclizing agent for the room temperature one-pot synthesis of 2-substituted 4H-3,1-benzoxazin-4-one derivatives in high yields through a cyclodehydration reaction. Furthermore, the method was performed under mild conditions characterized by simplified pathways and workup, minimized energy, and fewer reaction steps, compared with the previous methods. The proposed method, which is a simpler alternative than the published methods, is applicable for the synthesis of other 2-substituted 4H-3,1-benzoxazin-4-one derivatives.
authors.affiliation: School of Chemical Science and Food Technology, Faculty of Science and Technology, University Kebangsaan Malaysia (UKM), 43600, Selangor, Malaysia. sm.shariat@yahoo.com.
authors.forename: Mehdi
authors.initials: M
authors.lastname: Shariat
authors.forename: Mohd Wahid
authors.initials: MW
authors.lastname: Samsudin
authors.forename: Zuriati
authors.initials: Z
authors.lastname: Zakaria
references.citation: Org Lett. 2002 Feb 21;4(4):553-5
references.pmid: 11843589
references.citation: J Org Chem. 2002 Aug 23;67(17):6272-4
references.pmid: 12182679
references.citation: Acta Chim Slov. 2012 Sep;59(3):664-9
references.pmid: 24061324
references.citation: Pharmazie. 2004 Oct;59(10):753-5
references.pmid: 15544052
references.citation: Nature. 2001 Sep 20;413(6853):257
references.pmid: 11565009
references.citation: Chem Soc Rev. 2010 Jan;39(1):301-12
references.pmid: 20023854
references.citation: J Org Chem. 2005 Mar 18;70(6):2361-3
references.pmid: 15760232
references.citation: Biochimie. 2005 Feb;87(2):223-30
references.pmid: 15760716
references.citation: Acta Crystallogr Sect E Struct Rep Online. 2008 Dec 17;65(Pt 1):o127
references.pmid: 21581588
references.citation: J Org Chem. 2001 Nov 16;66(23):7907-9
references.pmid: 11701058