RESUMO
1-Alkyl-2-alkylthioquinolinium salts were prepared from 1-alkyl-2(1H)-quinolones via 1-alkyl-2(1H)-thioquinolones in two steps. Under mild conditions, the reaction of 1-alkyl-2-alkylthioquinolinium iodides with active methylene compounds in the presence of sodium hydride afforded 1-alkyl-1,2-dihydro-2-(substituted methylene)quinolines in good yields. The cyclization of 1-benzylquinolines using acetic anhydride produced the corresponding pyrrolo[1,2-a]quinoline derivatives.
Assuntos
Pirróis/química , Quinolinas/química , Anidridos Acéticos , Cromatografia em Camada Fina , Ciclização , Indicadores e Reagentes , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Espectroscopia de Infravermelho com Transformada de FourierRESUMO
The carbon-carbon bond-forming reactions of 1-methyl-2-methylthiophenylpyridinium iodides with active methylene compounds (such as dimethyl malonate, malononitrile) using NaH as a base gave the 2-substituted methylene-1,2-dihydropyridine derivatives.
Assuntos
Malonatos/química , Nitrilas/química , Compostos de Piridínio/química , Anidridos/química , Química Orgânica , Fenômenos de Química Orgânica , Compostos de Piridínio/síntese química , Sódio/químicaRESUMO
2-Alkyl-1-alkylthioisoquinolinium salts were readily prepared from 2-alkyl-1(2H)-isoquinolones via 2-alkyl1(2H)-thioisoquinolones in two steps. Under mild conditions, the reaction of 2-alkyl-1-alkylthioisoquinolinium salts with active methylene compounds in the presence of sodium hydride afforded 2-alkyl-1-(substituted methylene)iso-quinolines in good yields. Pyrrolo[2,1-a]isoquinolines were synthesized by the cyclization of 2-benzyl-1-(substituted methylene)isoquinolines using acetic anhydride.
