Triazines and related products. Part IX. Potential irreversible dihydrofolate reductase inhibitors

2,4-Diamino-s-triazines with a masked covalent labelling group

Sheila M Mackenzie, M F G Stevens

Research output: Contribution to journalArticle

Abstract

A series of 1,2,3-benzotriazin-4(3H)-ones carrying 3-(4,6-diamino-s- triazin-2-ylphenyl) substituents has been prepared by diazotisation of appropriately substituted o-aminobenzamides, or by cyclisation of o-methoxycarbonyl-phenyltriazenes in ethanol containing 2% piperidine. Cyclisation of 1-p-(4,6-diamino-s-triazin-2-yl)phenyl-3-o-cyanophenyltriazene in ethanol-piperidine affords 3-p-(4,6-diamino-s-triazin-2-yl)phenyl-3,4-dihydro- 4-imino-1,2,3-benzotriazine, which in 2N-hydrochloric acid rearranges to the isomeric substituted 4-anilino-1,2,3-benzotriazine. 4-p-Cyanoanilino-1,2,3- benzotriazine decomposes in alcohols containing 1% potassium hydroxide to give ethers; the scope of this reaction has been investigated.

Original languageEnglish
Pages (from-to)295-298
Number of pages4
JournalJournal of the Chemical Society, Perkin Transactions 1
DOIs
Publication statusPublished - 1972

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Folic Acid Antagonists
Triazines
Labeling
Cyclization
Ethanol
Ethers
Hydrochloric Acid
Alcohols
formoguanamine
piperidine

Cite this

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title = "Triazines and related products. Part IX. Potential irreversible dihydrofolate reductase inhibitors: 2,4-Diamino-s-triazines with a masked covalent labelling group",
abstract = "A series of 1,2,3-benzotriazin-4(3H)-ones carrying 3-(4,6-diamino-s- triazin-2-ylphenyl) substituents has been prepared by diazotisation of appropriately substituted o-aminobenzamides, or by cyclisation of o-methoxycarbonyl-phenyltriazenes in ethanol containing 2{\%} piperidine. Cyclisation of 1-p-(4,6-diamino-s-triazin-2-yl)phenyl-3-o-cyanophenyltriazene in ethanol-piperidine affords 3-p-(4,6-diamino-s-triazin-2-yl)phenyl-3,4-dihydro- 4-imino-1,2,3-benzotriazine, which in 2N-hydrochloric acid rearranges to the isomeric substituted 4-anilino-1,2,3-benzotriazine. 4-p-Cyanoanilino-1,2,3- benzotriazine decomposes in alcohols containing 1{\%} potassium hydroxide to give ethers; the scope of this reaction has been investigated.",
author = "Mackenzie, {Sheila M} and Stevens, {M F G}",
year = "1972",
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language = "English",
pages = "295--298",
journal = "Journal of the Chemical Society, Perkin Transactions 1",
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TY - JOUR

T1 - Triazines and related products. Part IX. Potential irreversible dihydrofolate reductase inhibitors

T2 - 2,4-Diamino-s-triazines with a masked covalent labelling group

AU - Mackenzie, Sheila M

AU - Stevens, M F G

PY - 1972

Y1 - 1972

N2 - A series of 1,2,3-benzotriazin-4(3H)-ones carrying 3-(4,6-diamino-s- triazin-2-ylphenyl) substituents has been prepared by diazotisation of appropriately substituted o-aminobenzamides, or by cyclisation of o-methoxycarbonyl-phenyltriazenes in ethanol containing 2% piperidine. Cyclisation of 1-p-(4,6-diamino-s-triazin-2-yl)phenyl-3-o-cyanophenyltriazene in ethanol-piperidine affords 3-p-(4,6-diamino-s-triazin-2-yl)phenyl-3,4-dihydro- 4-imino-1,2,3-benzotriazine, which in 2N-hydrochloric acid rearranges to the isomeric substituted 4-anilino-1,2,3-benzotriazine. 4-p-Cyanoanilino-1,2,3- benzotriazine decomposes in alcohols containing 1% potassium hydroxide to give ethers; the scope of this reaction has been investigated.

AB - A series of 1,2,3-benzotriazin-4(3H)-ones carrying 3-(4,6-diamino-s- triazin-2-ylphenyl) substituents has been prepared by diazotisation of appropriately substituted o-aminobenzamides, or by cyclisation of o-methoxycarbonyl-phenyltriazenes in ethanol containing 2% piperidine. Cyclisation of 1-p-(4,6-diamino-s-triazin-2-yl)phenyl-3-o-cyanophenyltriazene in ethanol-piperidine affords 3-p-(4,6-diamino-s-triazin-2-yl)phenyl-3,4-dihydro- 4-imino-1,2,3-benzotriazine, which in 2N-hydrochloric acid rearranges to the isomeric substituted 4-anilino-1,2,3-benzotriazine. 4-p-Cyanoanilino-1,2,3- benzotriazine decomposes in alcohols containing 1% potassium hydroxide to give ethers; the scope of this reaction has been investigated.

U2 - 10.1039/P19720000295

DO - 10.1039/P19720000295

M3 - Article

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JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

SN - 1472-7781

ER -