RESUMO
Treatment of 2-cyano-1,3-indandione (1) with aldimines gave the expected Mannich bases (2-4), while the arylidenes (7,8) were obtained when 2-ethoxycarbonyl-1,3-indandione (5) was subjected to react with aldimines. On the other hand, treatment of 2-acetyl-1,3-indandione (9) with aldimines gave compounds (11,12,14). The reaction of 2-phenyl-1,3-indandione (15) with aldimines gave the arylamino and the ethylene diamino derivatives (17, 18). Pictet Spengler reaction of 19b gave the spiro compound (21).
Assuntos
Iminas/química , Indanos/química , Indicadores e Reagentes , Espectroscopia de Ressonância MagnéticaRESUMO
Treatment of 2,3a,4,6,7a,8-hexahydrobenzo [1,2-c; 4,5-c] dipyrazole-3,7-dione (1) with chloroacetyl chloride gave the 2,6-bis (chloroacetyl) derivative (2), which on treatment with acetic anhydride pyridine afforded (3). Compound (2) when heated with pyridine afforded (1). Compound (1) underwent Mannich reaction with piperidine or morpholine and formaldehyde to give the 2,6-bis (piperidino or morpholinomethyl) derivatives (4a,b). Hydroxymethylation of (1) with formaldehyde gave the 2,6-bis (hydroxylmethyl) derivative (4), which on heating with piperidine afforded (4a), Reaction of 2,3a,4,6,7a,8-hexahydro- 2,6-bis (phenylsulphonyl) benzo [1,2-c; 4,5-c] dipyrazole-3,7-dione (7) with phenylmagnesium bromide gave dodecahydro-3,3,4a,7,7,8a-hexaphenyl-2,6- bis (phenylsulphonyl) benzo [1,2-c; 4,5-c] dipyrazole (8). Derivatives of hexahydrobenzodipyrazolone (9a-g) have been subjected to general screening for their antimicrobial activity.
Assuntos
Antibacterianos/síntese química , Bactérias/efeitos dos fármacos , Pirazóis/síntese química , Acetilação , Alquilação , Antibacterianos/química , Antibacterianos/farmacologia , Indicadores e Reagentes , Testes de Sensibilidade Microbiana , Pirazóis/química , Pirazóis/farmacologiaRESUMO
The behaviour of 3-acetylcarbostyril derivative 1, towards the Mannich reaction and the reactivity of the products formed in their reactions with aniline, phenylhydrazine and benzenesulphonyl chloride were studied. Furthermore, the reaction of 1 with thioglycolic acid was also investigated.