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

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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

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 cyanur...

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2-Phenyl-4H-3,1-benzoxazin-4-one

The title mol-ecule, C(14)H(9)NO(2), is nearly planar with a dihedral angle of 3.72 (4)° beteewn the plane of the phenyl ring and the 3,1-benzoxazin-4-one fragment. The mol-ecules are arranged into stacks parallel to the b axis via π-π stacking inter-actions [centroid-centroid distance = 4.2789 (11) Å] and the crystal packing is additionally stabilized by weak inter-molecular C-H⋯O inter-actions.

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One-pot three component synthesis of 2-amino-4H-chromenes under green and high efficient conditions

A simple, mild and high efficient procedure for one pot three component synthesis of 2-amino 4-H chromene derivatives was studied. The reaction was performed in water using aryl aldehydes, malononitrile and resorcinol, phloroglucinol or naphthole in the presence of N-methyl D-glucamine (Meglumine) as a green high efficient catalyst. The reaction was studied in thermal, microwave (MW) and ultras...

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One-pot three component synthesis of 2-amino-4H-chromenes under green and high efficient conditions

A simple, mild and high efficient procedure for one pot three component synthesis of 2-amino 4-H chromene derivatives was studied. The reaction was performed in water using aryl aldehydes, malononitrile and resorcinol, phloroglucinol or naphthole in the presence of N-methyl D-glucamine (Meglumine) as a green high efficient catalyst. The reaction was studied in thermal, microwave (MW) and ultras...

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Synthesis of benzoxazinone derivatives: a new route to 2 (N phthaloylmethyl)-4H-3,1-benzoxazin-4-one.

A new method has been designed to prepare the known benzoxazinone derivative 2-(N-phthaloylmethyl)-4H-3,1-benzoxazin-4-one (4). The acyl chloride derivative N-phthaloylglycine reacts with anthranilic acid in chloroform, in the presence of triethylamine, to give an intermediate that is then reacted with cyanuric chloride, used as a cyclization agent, to produce the benzoxazinone derivative.

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ژورنال

عنوان ژورنال: Chemistry Central Journal

سال: 2013

ISSN: 1752-153X

DOI: 10.1186/1752-153x-7-58