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

Mehdi Shariat, Mohd Wahid Samsudin, Zuriati Zakaria

Research output: Contribution to journalArticle

7 Citations (Scopus)

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.

Original languageEnglish
Article number58
JournalChemistry Central Journal
Volume7
Issue number1
DOIs
Publication statusPublished - 27 Mar 2013
Externally publishedYes

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Dimethylformamide
Cations
Derivatives
Heterocyclic Compounds
Medical applications
Industrial applications
cyanuric chloride

Keywords

  • Benzoxazinone
  • Cyclizing agent
  • Cyclodehydration
  • Iminium cation

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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. / Shariat, Mehdi; Samsudin, Mohd Wahid; Zakaria, Zuriati.

In: Chemistry Central Journal, Vol. 7, No. 1, 58, 27.03.2013.

Research output: Contribution to journalArticle

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AB - 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.

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