236-04-4

Upstream product

• 95379-90-1 Phenanthren-9,10-diyldiamin-dihydrochlorid 
• 32723-14-1 3-hydroxyphenanthro<9,10-e>-1,2,4-triazine 
• 252054-91-4 10-(trimethylsilyl)phenanthren-9-yl trifluoromethanesulfonate 
• 573-17-1 9-bromophenanthrene 

Relevant academic research and scientific papers

Substitution reactions of phenanthro[9,10-d]triazole with benzyl chlorides

The reaction of the potassium salt of phenanthro[9,10-d]triazole and benzyl chloride gave 2-(benzyl)-2H-phenanthro[9,10-d]triazole (2a) in 15% yield. The other regio-isomer, 1-(benzyl)-1H-phenanthro[9,10-d]-triazole (1a), was obtained as a by-product in 3.9% yield. Similar reactions with benzyl chlorides having a methyl, a chloro or a nitro group on the aromatic ring gave the corresponding two products, 1b-j and 2b-j. In all cases, 2b-j were major products in yields of 14-62%, 1b-j were minor ones in yields of 1.4-7.6%. The structures of the isomers were confirmed by X-ray crystal analyses.

Selective Synthesis of N-H and N-Aryl Benzotriazoles by the [3 + 2] Annulation of Sodium Azide with Arynes

The synthetic utility of NaN3 as the azide component in the [3 + 2] annulation with arynes generated from 2-(trimethylsilyl)aryltriflates resulting in the transition-metal-free synthesis of N-H and N-aryl benzotriazoles has been demonstrated. Using CsF as the fluoride source in CH3CN, the N-H benzotriazoles are formed in high selectivity instead of the expected azidobenzene. Interestingly, N-aryl benzotriazoles are formed using KF and THF as solvent in an open-flask reaction. Moreover, a method for the N1-arylation of benzotriazole is also presented.

A step-economical route to fused 1,2,3-triazoles via an intramolecular 1,3-dipolar cycloaddition between a nitrile and an in situ generated aryldiazomethane

An intramolecular 1,3-dipolar cycloaddition strategy for rapid entry into triazole-fused heterocyclic compounds without recourse to the traditional Cu(1)-catalyzed azide-alkyne cycloadditions is described. Central to the strategy is the in situ generation of substituted diazomethanes in a two-step sequence from the corresponding aldehydes, which then undergo smooth cycloaddition with a cyano group to generate the desired fused 1,2,3-triazoles in good overall yields. The entire sequence can be carried out in a onepot operation.

Novel heterocyclic analogs of trityl radicals: Synthesis and dimerization of diarylmethyl-1H-1,2,4-triazoles and diarylmethyl-2H- phenanthro[9,10-d]-1,2,3-triazoles

Diarylmethanes (1a-h, 9a-i and 12) containing a heterocyclic group attached to the central carbon atom have been synthesized. Lithiation of these substrates followed by the addition of iodine gave dimers (2a,b,d,e and 10) via α, para-dimerization of novel heterocyclic diarylmethyl radical intermediates.