Triazines and related products. Part VI. Synthesis and properties of 4-Amino-2(2H)-imino-s-triazino[1,2-c][1,2,3]-benzotriazines

Sheila M Mackenzie, M F G Stevens

Research output: Contribution to journalArticle

Abstract

2,4-Diamino-6-aryl-s-triazines (III) have been prepared for examination as potential tumour-inhibitory agents. 2,4-Diamino-6-(2-aminophenyl)-s-triazines (IV) react with formic acid and triethyl orthoformate to form the formylaminophenyl- and ethoxymethyleneaminophenyl-s-triazines respectively, but in formamide 4-aminoquin-azolines are produced. Diazotisation of the amines (IV) afforded in certain instances stable diazonium salts (X) which cyclised in base to derivatives of s-triazino[1,2-c][1,2,3]benzotriazine (XI). Replacement of the diazo-group in the s-triazinobenzotriazines (XI) by hydrogen, and by amino-, chloro-, hydroxy- and azonaphthol substituents demonstrates the similarity between the chemical properties of 1,2,3-benzotriazines and diazonium compounds. Reduction of the s-triazinobenzotriazines with stannous chloride in ethanol yielded s-triazino-[1,2-b]indazoles (XIV), which were also formed by cyclo-deamination of the hydrazines (XV) and by thermolysis of the azides (XVII). The s-triazinobenzotriazenes decompose homolytically in boiling nitrobenzene to afford a mixture of isomeric nitrobiphenyls : the mass spectra of the isomers are discussed.

Original languageEnglish
Pages (from-to)2298-2308
Number of pages11
JournalJournal of the Chemical Society C: Organic
Issue number17
Publication statusPublished - 1970

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Triazines
formic acid
Diazonium Compounds
Indazoles
Hydrazines
Thermolysis
Azides
Isomers
Boiling liquids
Chemical properties
Amines
Tumors
Hydrogen
Ethanol
Salts
Derivatives

Cite this

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title = "Triazines and related products. Part VI. Synthesis and properties of 4-Amino-2(2H)-imino-s-triazino[1,2-c][1,2,3]-benzotriazines",
abstract = "2,4-Diamino-6-aryl-s-triazines (III) have been prepared for examination as potential tumour-inhibitory agents. 2,4-Diamino-6-(2-aminophenyl)-s-triazines (IV) react with formic acid and triethyl orthoformate to form the formylaminophenyl- and ethoxymethyleneaminophenyl-s-triazines respectively, but in formamide 4-aminoquin-azolines are produced. Diazotisation of the amines (IV) afforded in certain instances stable diazonium salts (X) which cyclised in base to derivatives of s-triazino[1,2-c][1,2,3]benzotriazine (XI). Replacement of the diazo-group in the s-triazinobenzotriazines (XI) by hydrogen, and by amino-, chloro-, hydroxy- and azonaphthol substituents demonstrates the similarity between the chemical properties of 1,2,3-benzotriazines and diazonium compounds. Reduction of the s-triazinobenzotriazines with stannous chloride in ethanol yielded s-triazino-[1,2-b]indazoles (XIV), which were also formed by cyclo-deamination of the hydrazines (XV) and by thermolysis of the azides (XVII). The s-triazinobenzotriazenes decompose homolytically in boiling nitrobenzene to afford a mixture of isomeric nitrobiphenyls : the mass spectra of the isomers are discussed.",
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Triazines and related products. Part VI. Synthesis and properties of 4-Amino-2(2H)-imino-s-triazino[1,2-c][1,2,3]-benzotriazines. / Mackenzie, Sheila M; Stevens, M F G.

In: Journal of the Chemical Society C: Organic, No. 17, 1970, p. 2298-2308.

Research output: Contribution to journalArticle

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AB - 2,4-Diamino-6-aryl-s-triazines (III) have been prepared for examination as potential tumour-inhibitory agents. 2,4-Diamino-6-(2-aminophenyl)-s-triazines (IV) react with formic acid and triethyl orthoformate to form the formylaminophenyl- and ethoxymethyleneaminophenyl-s-triazines respectively, but in formamide 4-aminoquin-azolines are produced. Diazotisation of the amines (IV) afforded in certain instances stable diazonium salts (X) which cyclised in base to derivatives of s-triazino[1,2-c][1,2,3]benzotriazine (XI). Replacement of the diazo-group in the s-triazinobenzotriazines (XI) by hydrogen, and by amino-, chloro-, hydroxy- and azonaphthol substituents demonstrates the similarity between the chemical properties of 1,2,3-benzotriazines and diazonium compounds. Reduction of the s-triazinobenzotriazines with stannous chloride in ethanol yielded s-triazino-[1,2-b]indazoles (XIV), which were also formed by cyclo-deamination of the hydrazines (XV) and by thermolysis of the azides (XVII). The s-triazinobenzotriazenes decompose homolytically in boiling nitrobenzene to afford a mixture of isomeric nitrobiphenyls : the mass spectra of the isomers are discussed.

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