Studies on Condensed Systems of Aromatic Nitrogenous Series. XXI. Mode of Formation of Quinazoline 3-Oxides from Quinazoline and Hydroxylamine.

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概要

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• On the evidence of the following experimental results the chemical structures (I) and (II) were assigned respectively to the intermediates, C_<16>H_<15>O_3N_5 (I) and C_8H_9O_2N_3 (II), which were prepared by the reaction of quinazoline and hydroxylamine. (1) On alkaline decomposition, (II) gave formic acid, ammonia, and o-aminobenzal-dehyde oxime. (2) By the action of hydroxylamine and sodium acetate mixture, (II) formed o-formamidobenzaldehyde oxime. (3) Quinazoline 3-oxide was obtained by terating (I) or (II) with acetone or p-nitrobenzaldehyde, by formylation of o-aminobenzaldehyde oxime with formic acid or ethyl orthoformat, and by dehydration of o-formylaminobenzaldehyde oxime with conc. sulfuric acid. (4) (I) behaved like (II) toward ferric chloride, acetone, and sodium hydroxide and was proved to be a molecular compound of quinazoline 3-oxide and (II). Also, based on the chemical structure of the intermediates, the mechanism of the specific hydroxylamine reaction shown in Chart 3 is proposed.

• 公益社団法人日本薬学会の論文
• 1959-06-10

著者

• 足立 亀久夫

  Pharmaceutical Faculty University Of Kanazawa

関連論文

• Studies on Condensed Systems of Aromatic Nitrogenous Series. XXI. Mode of Formation of Quinazoline 3-Oxides from Quinazoline and Hydroxylamine.

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