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A versatile and efficient palladium catalyzed domino reaction leading to a broad range of substituted 1-aminoindoles has been developed. The title compounds were prepared from 2-halo-phenylacetylenes and simple hydrazines in good to excellent yields in just a few hours under mild conditions. more...

A sequential Pd-catalyzed amidation—Fe-mediated reductive aminocyclization of o-chloronitro(het)arenes with aromatic or aliphatic amides provides an efficient access towards benzimidazole derivatives. more...

The present new general palladium-catalyzed procedure for the cross-coupling of (hetero)aryl tosylates provides a facile access to various functionalized (hetero)aryl alkynes tolerating many functional groups. more...

The synthesis of 4-aryl-5-methoxy-, 5-aryl-4-methoxy- and 4,5-diaryl-3(2H)-pyridazinones via Suzuki palladium-catalysed cross-coupling reactions with the corresponding chloro-3(2H)-pyridazinones is described. more...

4,5-Dialkynyl-2-(methyl or phenyl)-3(2H)-pyridazinones (2a–c) were efficiently prepared via Sonogashira cross-coupling reaction on 4,5-dichloro-2-(methyl or phenyl)-3(2H)-pyridazinones (1a,b). Selective Sonogashira reactions were successfully achieved on 4-chloro-2-methyl-5-trifluoromethanesulfonyloxy- (6) and 5-chloro-2-methyl-4-trifluoromethanesulfonyloxy-3(2H)-pyridazinone (11), yielding 5-alkynyl-4-chloro- (7a–c) and 4-alkynyl-5-chloro-2-methyl-3(2H)-pyridazinones (3a,c,e), respectively. Compounds 7a–c and 3a,c,e were subjected to a second Sonogashira reaction giving 4,5-dialkynyl-2-methyl-3(2H)-pyridazinones (8a–c) bearing two different acetylene substituents. Suzuki cross-coupling reaction was also achieved on compounds 7a and 3a producing 4-aryl-5-phenylethynyl- and 5-aryl-4-phenylethynyl-2-methyl-3(2H)-pyridazinones, respectively, in excellent yield. more...

A new synthetic route towards the synthesis of 1,6-dihydro-7H-pyrrolo[2,3-d]pyridazin-7-ones (10a-f) and their regioisomers 1,5-dihydro-4H-pyrrolo[2,3-d]pyridazin-4-ones (9a,b) is described, based on the reaction of 5-alkynyl-4-chloro- (7a,b) and 4-alkynyl-5-chloropyridazinones (8) with different amines (ammonia, methylamine and propylamine) followed by a treatment with a NaOEt solution. more...

A study of the reactivity of 5-alkynyl-4-chloro- (la,b) and 4-alkynyl-5-chloropyridazin-3(2H)-ones (4a,b) towards oxygen and sulfur nucleophiles (NaOCH 3 , NaSCH 3 , KOH and Na 2 S) is reported. The synthesis of 5-alkynyl-2-methyl-4-methoxy- (2a,b) and 5-alkynyl-2-methyl-4-methylthiopyridazin-3(2H)-ones (3a,b) and their regioisomers 4-alkynyl-2-methyl-5-methoxy- (5a,b) and 4-alkynyl-2-methyl-5-methylthiopyridazin-3(2H)-ones (6a,b) is described, as well as the synthesis of 2-substituted 6-methylfuro[2,3-d]- (7a,b,c) and 2-substituted 6-methylthieno[2,3-d]pyridazin-7(6H)-ones (8a,b) and their regioisomers 2-substituted 5-methylfuro[2,3-d]- (9a,b,c) and 2-substituted 5-methylthieno[2,3-d]pyridazin-4(5H)-ones (10a,b). more...