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

Fingerprint Dive into the research topics of 'Triazines and related products. Part III. Synthesis and rearrangement of 3,4-dihydro-4-imino-1,2,3-benzotriazines'. Together they form a unique fingerprint.

  • Cite this