Photochemistry of N-heterocycles. Part 1. Synthesis and photochemistry of some 2(4),5-dihydro-1,2,4-triazines. X-ray molecular structure of 1-(4-methyl-3,5,6-triphenyl-1,4,5,6-tetrahydro-1,2,4-triazin-6-yl)ethanol

József Nagy, József Nyitrai, Pál Kolonits, Károly Lempert, Anna Gergely, László Párkányi, Alajos Kálmán

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Ethanolic solutions of the hydrochlorides of the mostly new 2(4),5-dihydro-1,2,4-triazines (1)-(4) were irradiated with a high-pressure mercury immersion lamp (λ ≥ 300 nm). The salts (Ia)-(3a) underwent reductions, ring contractions, and dehydrogenations upon irradiation to yield pyrazoles (5) and (6) along with phenanthroimidazoles (9) and (10). In addition, the 4-methyl-3,5,6-triphenyl-4,5-dihydro-1,2,4-triazinium chloride (3a) furnished the 6-(1-hydroxyethyl) adduct (11) whose structure was assigned on the basis of its 1H and 13C n.m.r. spectra, and an X-ray diffraction study. The 4-(3-hydroxypropyl)dihydrotriazinium chloride (4a) led, in addition to the expected pyrazole (5), to two new products: the aromatic triazine (15) and the oxazinotriazine (21) by photoelimination and intramolecular photosubstitution, respectively.

Original languageEnglish
Pages (from-to)3267-3274
Number of pages8
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number12
Publication statusPublished - Dec 1 1988

ASJC Scopus subject areas

  • Chemistry(all)

Fingerprint Dive into the research topics of 'Photochemistry of N-heterocycles. Part 1. Synthesis and photochemistry of some 2(4),5-dihydro-1,2,4-triazines. X-ray molecular structure of 1-(4-methyl-3,5,6-triphenyl-1,4,5,6-tetrahydro-1,2,4-triazin-6-yl)ethanol'. Together they form a unique fingerprint.

  • Cite this