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 language | English |
|---|---|
| Pages (from-to) | 295-298 |
| Number of pages | 4 |
| Journal | Journal of the Chemical Society, Perkin Transactions 1 |
| DOIs | |
| Publication status | Published - 1972 |
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Triazines and related products. Part IX. Potential irreversible dihydrofolate reductase inhibitors : 2,4-Diamino-s-triazines with a masked covalent labelling group. / Mackenzie, Sheila M; Stevens, M F G.
In: Journal of the Chemical Society, Perkin Transactions 1, 1972, p. 295-298.Research output: Contribution to journal › Article
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
SP - 295
EP - 298
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
SN - 1472-7781
ER -