37469-28-6

Upstream product

• 6942-03-6 α-benzamidylbenzyl phenyl ketone 
• 133406-37-8 3,5,6-triphenyl-2,5-dihydro-1,2,4-triazin-4-ium chloride 
• 120915-07-3 4-(3-hydroxypropyl)-3,5,6-triphenyl-4,5-dihydro-1,2,4-triazinium chloride 
• 133406-37-8 3,5,6-triphenyl-2⁽⁴⁾,5-dihydro-triazinium chloride 
• 24108-44-9 3,5,6-triphenyl-[1,2,4]triazine 
• 28867-76-7 benzaldehyde benzylidenehydrazone 

Downstream Products

• 222720-55-0 1,4-diacetyl-3,5,6-triphenyl-1,4-dihydro-1,2,4-triazine 
• 484-47-9 lophine 
• 58484-95-0 1-methyl-2-ohenyl-1H-phenanthro<9,10-d>imidazole 
• 33314-38-4 1-methyl-3,4,5-triphenyl-1H-pyrazole 
• 222720-56-1 4-acetylamino-3,4,5-triphenyl-4H-pyrazole 
• 18076-30-7 3,4,5-triphenylpyrazole 

Relevant academic research and scientific papers

Photochemistry of N-heterocycles, 5: A comparison of chemical and photochemically induced reduction of some 2(4),5-dihydro-1,2,4-triazines and aromatic 1,2,4-triazines

Chemical reduction (Zn/AcOH) of the arene 1 and of 2(4),5-dihydro-1,2,4- triazine 7 has been reinvestigated, resulting in the amendment of literature data concerning this reaction. Chemical, electrochemical, and photochemically induced reductions and ring contractions of 1,2,4-triazine derivatives have been compared. The first example of a triaryl-1,4-dihydrotriazine has been prepared. Some further evidence is presented that supports the proposed mechanism of the photochemically induced reduction and ring contraction of 1,2,4-triazines.

Photochemistry of N-Heterocycles. Part 3. Synthesis and Photochemistry of some New Dihydro-1,2,4-triazines and their Quaternary Salts

Several new dihydro-1,2,4-triazines, 1b, 4, 5, 16 and 19, have been synthesized and their structures unambiguously determined.The existence of 1,2- and 1,4-dihydrotriazines, 20 and 22, described in the literature was ruled out.Irradiation of the aromatic triazines 6 and 15 and the novel quaternary dihydro-1,2,4-triazinium salts 4, 5, 19 furnished new evidence for both the reduction pathways and the mechanism of ring-contraction reactions.

PHOTOCHEMISTRY OF N-HETEROCYCLES, II PHOTOCHEMICALLY INDUCED REDUCTION AND OXIDATION OF SOME 2(4),5-DIHYDRO-1,2,4-TRIAZINES, HIGH PRESSURE LIQUID CHROMATOGRAPHY STUDIES

The salts 1a-1c, 2a, and 3a of the 3,5,6-triphenyl-2(4),5-dihydro-1,2,4-triazines 1-3 were irradiated with a high pressure mercury immersion lamp (λ300 nm) in various alcohols and the reactions were followed by HPLC.The singlet excited states of the cations of the salts 1a-1c, 2a and 3a are thought to act as single electron acceptors.The resulting radicals A are converted by proton transfer into the radical cations B, which may become stabilized either by recombination with a hydroxyalkyl radical and proton loss to give the adduct 10, or by successive reduction and ring contractions to yield the corresponding pyrazoles 4 and 5, or the imidazoles 6 and 7.The latter are smoothly photodehydrogenated to the corresponding phenanthro-imidazoles 8 and 9.The photoexcited cation of salt 1a is able to dehydrogenate the base 1 to the aromatic triazine 11.When irradiated in alcohol possessing α-hydrogen atoms, compound 11 is reduced and furnishes the ring contraction products 4 and 8.The relative amounts of the pyrazole 4 and of the phenanthroimidazole 8 depend on whether compound 1 or 11 is used as the starting material.This observation suggests two independent pathways for the formation of compound 8.A mechanistic interpretation of the total photochemical process is presented.

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

Ethanolic solution 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 (1a)-(3a) underwent reductions, ring contractions, and dehydrogenations upo

THE REACTIONS OF HYDRAZONES AND RELATED COMPOUNDS WITH STRONG BASES. PART 4. 4,5-DIARYL-1,2,3-TRIAZOLES FROM AROMATIC ALDEHYDE AZINES AND FROM THE REACTION OF ARENECARBONITRILES WITH ARYLDIAZOMETHANES

Reaction of aromatic aldehyde azines in dimethyl sulphoxide at 20 deg C with potassium t-butoxide gave 4,5-diaryl-1,2,3-triazoles (4) and stilbenes.Mechanisms were studied by addition of possible intermediates and by (14)C tracer methods.The synthesis of 4,5-diaryl-1,2,3-triazoles from arenecarbonitriles, aryldiazomethanes, and potassium t-butoxide in toluene is described and the mechanism is discussed.