The reported structures of reaction products of enaminones with malononitrile in ethanolic piperidine are revised. A novel route to 2,3-dihydropyridazine-4-carboxylic acids 4a-c via reactions of 2-cyano-5-(dimethylamino)-5-arylpenta-2,4-dienamides 8a-c with nitrous acid or with benzenediazonium chloride is reported. Compounds 8a-c are converted to 1,2-dihydropyridine-3-carboxylic acid and 1,2-dihydropyridine-3-carbonitrile derivatives upon reflux in EtOH/ HCl and in AcOH.
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A green, simple and highly efficient synthesis of N,N-diarylsubstituted formamidines has been developed employs reaction of triethylorthoformate (TEO) with aromatic amines catalyzed by cerium (IV) ammonium nitrate (CAN) in water at ambient temperature. This method offers the advantages of proceeding under environmentally friendly technique with high yields and simplicity either in conducting the reaction or handling the products.
A diversity of new 7-substituted[1,2,4]triazolo[1,5-a]pyrimidine and 6-substituted[1,2,4]triazolo[1,5-a] pyrimidine-7-amine derivatives has been synthesized via reaction of 3-amino-[1,2,4]triazole with enaminonitriles and enaminones. The regio orientation and the structure of the products were confirmed by spectral and analytical data and synthesis via an alternative route. The procedure proved to be simple, efficient, and high yielding, and diversities of [1,2,4]triazolo[1,5-a]pyrimidines were obtained.
KEYWORDSEthyl 2-amino-3-cyano-4-phenylnicotinates (8), could be readily synthesized via reacting ethyl propiolate with benzylidenemalononitrile in the presence of L-proline as a catalyst and subsequent rearrangement of the so formed 2-aminopyran (7), with acetic acid in the presence of ammonium acetate. A series of 2-amino and 2-hydroxyarylazonicotinates monoazo disperse dyes (12a-c), were prepared in a good yields via condensation of arylhydrazonals (11a-c), with active methylene nitriles. The compound 9 was also characterized by single crystal X-ray diffraction studies. Crystal data for compound 9, C15H18O6 (M = 294.29): hexagonal, space group P65 (no. 170), a = 11.3311 (5)
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