Synthetic Approaches Towards 1,2,4-Triazines Utilizing Wittig and Wittig-Horner Reagents

Authors: Arsanious, Mona¹; Moharam, Maysa²

Source: Phosphorus, Sulfur, and Silicon and the Related Elements, Volume 183, Number 9, September 2008 , pp. 2344-2359(16)

Publisher: Taylor and Francis Ltd

Abstract:

The reaction of 5-aroyl-1,2,4-triazin-6(1H)-ones 2a, 2b with methoxycarbonyl-, ethoxycarbonyl-, methylenetriphenylphosphorane (1a,1b) gave olefinic adducts 4a-4d, pyranotriazine products 5a-5d, and triphenylphosphine oxide. Moreover, benzoylmethylenetriphenylphosphorane (1c) reacts with 5-[(4-methoxyphenyl) carbonyl]-3-phenyl-1,2,4-triazin-6(1H)-one (2b) to yield 4e and triphenylphosphine oxide. On the other hand, the application of phosphorus ylides on 5-[(hydroxyimino) (4-methoxyphenyl)methyl]-3-phenyl-1,2,4-triazin-6(1H)-one (3b) render the new product tetraazabenzocyclohepten-8-one oxide 6, and triphenylphosphine oxide. Trimethylphosphonoacatate 7 reacts with 5-aroyl-1,2,4-triazin-6(1H)-ones 2a, 2b to afford 5,6-dihydro-5-hydroxy-3,5-diarylpyrano[3,2-e][1,2, 4]-triazin-7-ones 8a, 8b and alkylated adducts 9a, 9b. Moreover, 5-[(hydroxyimino)aryl methyl]-3-phenyl-1,2,4-triazin-6(1H)-ones 3a, 3b react with Wittig-Horner reagent to give alkylated products 10a, 10b and isoxazolo [4,5-e]-1,2,4-triazines 11a, 11b. The biological activity of the new synthesized compounds was also examined. Possible reaction mechanisms are considered and the structural assignments are based on analytical and spectroscopic results.

Keywords: 5-Aroyl-1,2,4-triazinones; 5-[(hydroxyimino)arylmethyl]-3-phenyl-1,2,4-triazi; phosphonium ylides; Wittig-Horner reagent

Document Type: Research article

DOI: http://dx.doi.org/10.1080/10426500802077606

Affiliations: 1: Organometallic and Organometalloid Chemisrty Department, National Research Centre, Dokki, Cairo, Egypt 2: Microbial Chemistry Department, National Research Centre, Dokki, Cairo, Egypt

Publication date: 2008-09-01

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