1,2,3-Benzotriazole, synthesis

However, there are differences between o-phenylenediamine and 4,5-diaminopyrazoles in the synthesis of [5.5] systems. For example, the formation of pyrazolo[3,4-d]-[l,2,3]triazole (550) is similar to that of benzotriazole, but all attempts to extend the synthesis of benzimidazoles to the preparation of the imidazo[4,5-c]pyrazole system (551) have failed (78TH40400). 

H-l,2,3-Benzotriazole, 2-phenyl-oxidation, 5, 721 as photostabilizers, 5, 731 synthesis, 5, 722 Benzotriazoles acylation, 5, 54 antifogging agents... 

Advances in synthetic methodology using benzotriazole 99JHC1501. Application of benzotriazole in synthesis and transformations of heterocycles 98JHC1123. 

The reaction also proceeds readily with A/-monosubstituted 1,2-diaminobenzenes (6.45, R = alkyl, aryl, acyl). Kroupa and Matrka (1970) investigated optimal reaction conditions for the synthesis of 1,2,3-benzotriazole from 1,2-diaminobenzene. 

An alternative approach towards the PASP synthesis of isocyanides was developed by Bradley [100,101]. It involved the use of a polymer-supported sul-fonyl chloride in the presence of base to afford the dehydration of formamides (Scheme 21). The formamides required could be easily prepared by reaction of the corresponding amines with a formylated benzotriazole resin. Opti-... 

Hie reactions of 4-chloropyridines and quinolines 17 with benzotriazoles 18 in a modified Graebe-Ullman synthesis give excellent yields of Y arbolines and their benzo-fused derivatives 20. Excellent yields for preparation of the penultimate benzotriazole precursors 19 are reported as well. In the optimized one-pot conditions, the combined neat substrates are heated with microwave irradiation (MW) for short (7-10 min) durations. The crude 19 is treated with H4P2O7 and irradiated futher (4-6 min). The resultant y-carbolines 20 were methylated to form the quaternary salts. These were tested and found to lack DNA intercalation properties <96JOC5587>. 

A synthesis of 5-(aioylamino)-2-aryloxazoles 39 is outlined in Scheme 9. Heating the glycol 37 (Bt = benzotriazol-l-yl), prepared from glyoxal and benzotriazole, with an amide in the presence of an ion exchange resin yields the acylated diamine 38, which cyclises by the action of sodium hydiide in DMF <95JHC1651>. 

Schiemann K, Showalter HDH. Development of polymer-supported benzotriazole as a novel traceless linker for solid-phase organic synthesis. J Org Chem 1999 64 4972 1975. 

The synthesis of 4,5-diaryl-6-phenylsulfanyl-2,3-benzo-l,3a,6a-triazapentalenes 239 through Pummerer-type reactions of (benzotriazol-l-yl)allylic sulfoxides 238 with trifluoroacetic anhydride in THF has been reported (Equation 35) <2002EJ0493>. Similarly, unstable solid imines 240 treated without purification with trifluoroacetic anhydride (TFAA) provide 241 (Equation 36) <2003TL7507>. 

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