Triazines and related products. Part III. Synthesis and rearrangement of 3,4-dihydro-4-imino-1,2,3-benzotriazines

H N E Stevens, M F G Stevens

Research output: Contribution to journalArticle

Abstract

A series of 3-substituted-3,4-dihydro-4-imino-1,2,3-benzotriazines (V) have been prepared by cyclization of the appropriate o-cyanophenyltriazenes (IV) in 70% aqueous ethanol or in ethanol containing 2% piperidine. Triazenes with powerful electron-withdrawing substituants cyclize directly to substituted 4-anilino-1,2,3-benzotriazines (VI). Rearrangement of 3-aryl-3,4-dihydro-4-imino-1,2,3-benzotriazines to the isomeric 4-anilino-1,2,3-benzotriazines has been effected in ethanol or in 2N-hydrochloric acid and is facilitated by electron-withdrawing substituents in the aryl nucleus. The contrasting stabilities of 3-benzyl- and 3-phenethyl-3,4-dihydro-4-imino-1,2,3-benzotriazine have been attributed to a steric affect.

Original languageEnglish
Pages (from-to)765-771
Number of pages7
JournalJournal of the Chemical Society C: Organic
Issue number6
Publication statusPublished - 1970

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Triazines
Ethanol
Triazenes
Hydrochloric Acid
Electrons
Cyclization

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title = "Triazines and related products. Part III. Synthesis and rearrangement of 3,4-dihydro-4-imino-1,2,3-benzotriazines",
abstract = "A series of 3-substituted-3,4-dihydro-4-imino-1,2,3-benzotriazines (V) have been prepared by cyclization of the appropriate o-cyanophenyltriazenes (IV) in 70{\%} aqueous ethanol or in ethanol containing 2{\%} piperidine. Triazenes with powerful electron-withdrawing substituants cyclize directly to substituted 4-anilino-1,2,3-benzotriazines (VI). Rearrangement of 3-aryl-3,4-dihydro-4-imino-1,2,3-benzotriazines to the isomeric 4-anilino-1,2,3-benzotriazines has been effected in ethanol or in 2N-hydrochloric acid and is facilitated by electron-withdrawing substituents in the aryl nucleus. The contrasting stabilities of 3-benzyl- and 3-phenethyl-3,4-dihydro-4-imino-1,2,3-benzotriazine have been attributed to a steric affect.",
author = "Stevens, {H N E} and Stevens, {M F G}",
year = "1970",
language = "English",
pages = "765--771",
journal = "Journal of the Chemical Society C: Organic",
issn = "0022-4952",
publisher = "Chemical Society",
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Triazines and related products. Part III. Synthesis and rearrangement of 3,4-dihydro-4-imino-1,2,3-benzotriazines. / Stevens, H N E; Stevens, M F G.

In: Journal of the Chemical Society C: Organic, No. 6, 1970, p. 765-771.

Research output: Contribution to journalArticle

TY - JOUR

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AU - Stevens, M F G

PY - 1970

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