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Abstract: 5-Nitro-2-pyridone can be selectively N-phenacylated, and the resulting phenacylpyridones I undergo cyclization to 6-nitrooxazolo[3,2-a]pyridinium salts II. These salts II readily react with ammonia and aliphatic amines leading to the products of pyridine ring opening - previously unknown 1-amino-2-nitro-4-(oxazole-2-yl)butadienes-1,3. Reaction of salts II with water lead to hydrolytic cleavage of the oxazole fragment.

Abstract: A versatile method for the preparation of N-heteroaryl substituted aminoacid derivatives is suggested. The method avoids facile diketopiperazine formation.

Abstract: 4,5-disubstituted-thizolyl amides, derivatives of 4-hydroxy-piperidine and of 4-N-methyl piperazine, were synthesized and tested as anti-inflammatory agents. Log P values were theoretically calculated and experimentally determined. These compounds were tested for antioxidant activity, as hydroxyl radical scavengers and for their ability to interact with stable 1,1-diphenyl-2-picryl hydrazyl free radical (DPPH). The effect of the synthesized compounds on inflammation, using the carrageenin induced mice paw edema model was studied. Both anti-inflammatory and antioxidant activities depended on some structural characteristics of the synthesized compounds.

Abstract: A general synthetic methodology employing heteroaryl-aryl Suzuki coupling is reviewed, by which 15 heteroaromatic ring systems of biological interest have been prepared.

Abstract: Vitamin D₃ and its synthetic analogs are promising compounds for controlling various types of cell differentiation. In this article, we describe the synthesis of novel vitamin D₃ analogs containing heteroatoms in their side chains – so-called vitamin D3 lactam analogs – via 1,3-dipolar cycloaddition reaction as a key step.

Abstract: 3-Methyl-5-nitropyrimidin-4(3H)-one readily reacts with carbonyl compounds to produce three kinds of ring transformations. The nitropyrimidinone behaves as the synthetic equivalent of activated diformylamine affording 3,5-difunctionalized 4-pyridones, 4,5-disubstituted pyrimidines and functionalized 4-aminopyridines. It also behaves like α-nitro-formylacetic acid to give 5,6-disubstituted 3-nitro-2-pyridones.

Abstract: Two different approaches are offered for the synthesis under mild conditions of disubstituted phenazinium and benzo[a]phenazinium salts. Direct nucleophilic substitutions by primary and secondary amines in quaternary phenazinium salts containing an additional positive charge in the aliphatic part of the molecule were carried out. The substitution proceeds successively in positions 2 and 7, which allows selective introduction of different substituents into the heterocycle. Direct nucleophilic substitution in quaternary 2-N-alkyl-acetamidophenazinium and 5-alkoxy-benzo[a]phenazinium salts with different amines can also serve as a convenient method for the introduction of two different substituents.

Table of Contents

Molecules, Volume 8, Issue 6 (June 2003), Pages 459-519