Reaction of 1H-azoles with 2-hydroxybenzyl alcohols

Condensation of 1H-azoles with 2-hydroxybenzyl alcohols gave a series 2-(1H-azol-1-ylmethyl)phenols. 12H-Benzimidazo[2,1-b][1,3]benzoxazine was synthesized from 2-methylmercaptobenzimidazole and 2-hydroxybenzyl alcohol. The X-ray diffraction data of 7-nitro-2,3-diphenyl-5H-imidazo[2,1-b]-[1,3]benzoxazine are discussed. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, 1256–1263, August, 2007.     

New synthesis of 3-amino-1H-benzo[f]chromene-2-carbonitriles

3-Amino-1H-benzo[f]chromene-2-carbonitriles were synthesized by non-catalytic reaction from Mannich bases of the naphthalene series and malononitrile. Reactive 1-benzylidene(or methylidene)naphthalen-2(1H)-ones were presumed as intermediate products.     

Convenient one-step synthesis of 4-unsubstituted 2-amino-4H-chromene-2-carbonitriles and 5-unsubstituted 5H-chromeno[2,3-b]pyridine-3-carbonitriles from quaternary ammonium salts

We have reported DBU catalyzed synthesis of 4-unsubstituted 2-amino-4H-chromene-2-carbonitriles in water under reflux. The attractive features of this process are mild reaction conditions, short reaction times, easy isolation of products and good yields. 5H-chromeno[2,3-b]pyridine-3-carbonitriles were obtained by refluxing excess of malononitrile and quaternary ammonium salts in ethanol in the presence of NaOH as catalyst. The mechanisms of these reactions are believed to involve the formation of the o-quinone methide intermediate.