RESUMEN
2-Alkoxybenzo[h]quinoline-3-carbonitriles 2 were readily synthesized via Dimroth rearrangement of 2-amino-4-aryl-5,6-dihydro-4H-naphtho[1,2-b]pyran-3-carbonitriles 5 induced by ethanolic and methanolic KOH. Compounds 2 were also obtained by the reaction of 2-arylmethylidene-3,4-dihydro-1(2H)-naphthalenones 1 with malononitrile or of ylidenemalononitriles 4 with 1,2,3,4-tetrahydro-1-naphthalenone in ethanolic and methanolic KOH. The molluscicidal activity of the products towards Biomphalaria alexandrina snails was screened.
Asunto(s)
Moluscocidas/síntesis química , Nitrilos/síntesis química , Quinolinas/síntesis química , Animales , Biomphalaria , Espectroscopía de Resonancia Magnética , Moluscocidas/farmacología , Nitrilos/farmacología , Quinolinas/farmacología , Espectrofotometría InfrarrojaRESUMEN
Reaction of the propenones 1c, d with chlorosulfonyl isocyanate followed by hydrolysis gave the corresponding carbamoyloxybenzoates 2a, b. While their reaction with ethyl isocyanate afforded the 1,3-benzoxazine-2,4-diones 3a, b. Reaction of 1a, b with aryl hydrazines gave the pyrazolines 4a, d, whereas, with hydrazine hydrate in acetic acid, the acetyl derivatives 4e, f were produced. 1c, d reacted with malononitrile and ethyl cyanoacetate affording the cyanopyridines 5 and cyanopyridones 6 respectively. The products show antimicrobial activities.
Asunto(s)
Antiinfecciosos/síntesis química , Pirazoles/síntesis química , Piridinas/síntesis química , Salicilatos/síntesis química , Antibacterianos , Antiinfecciosos/farmacología , Bacterias/efectos de los fármacos , Hongos/efectos de los fármacos , Espectroscopía de Resonancia Magnética , Pruebas de Sensibilidad Microbiana , Pirazoles/farmacología , Piridinas/farmacología , Salicilatos/farmacología , Espectrofotometría Infrarroja , Espectrofotometría UltravioletaRESUMEN
A facile synthetic approach towards the synthesis of 2-substituted carbamoyl (or thiocarbamoyl)-3-aryl-3,3a,4,5-tetrahydro-2 H-benz[g]indazoles 3a-r and their 2-acylating derivatives 4-6 was reported via the reaction of 2-unsubstituted-2 H-benz[g]indazoles 2 with isocyanates or their thio analogues, acid anhydrides and aliphatic or aromatic carboxylic acids. The molluscicidal activity of the products was screened.
Asunto(s)
Biomphalaria/fisiología , Moluscocidas/síntesis química , Animales , Espectroscopía de Resonancia Magnética , Moluscocidas/toxicidad , Espectrofotometría InfrarrojaRESUMEN
Reaction of various fused pyran compounds with formic acid was studied. Thus, refluxing 6-aminopyrano[2,3-c]pyrazole-5-carbonitriles 3 with formic acid afforded the corresponding 3-aryl-3-(5-hydroxy-3-methyl-1H-pyrazole-4-yl)propanoic acids 4. Whereas, reaction of formic acid with 2-amino-4H-1-benzopyran-3-carbonitriles 6 gave the corresponding quinoline-2,5(1H,6H)-diones 7. The study was also extended towards many spiro compounds possessing pyran residue. The antimicrobial properties of the prepared compounds was screened.