Portal de Periódicos da CAPES

Synthesis of some 7‐substituted 3‐chloro‐3,4‐dihydro‐1‐hydroxycarbostyrils by the reduction cyclization of α‐chloro‐β‐(4‐substituted‐2‐nitrophenyl)propionic acids

1985; Wiley; Volume: 22; Issue: 1 Linguagem: Inglês

10.1002/jhet.5570220135

1943-5193

Tommy J. McCord, Michael Warner, P. L. SHAFER, Rose M. Davis Disher, Alvie L. Davis,

Synthesis and Characterization of Heterocyclic Compounds

Abstract A new method was developed for the synthesis of some 7‐substituted 3‐chloro‐3,4‐dihydro‐l‐hydroxycarbostyrils 3c‐g in which α‐chloro‐β‐(4‐substituted‐2‐nitrophenyl)propionic acids 2c‐g were reductively cyclized by catalytic hydrogenation over platinum‐on‐carbon sulfided catalyst. In particular, this method was applied to α‐chloro‐β‐(2‐nitrophenyl)propionic acids bearing 4‐methyl 2c , 4‐ethyl 2d , 4‐ethoxy 2e , 4‐( n ‐butyl 2f and 4‐phenyl 2g substituents to afford good yields of the corresponding 7‐methyl 3c , 7‐ethyl 3d , 7‐ethoxy 3e , 7‐( n ‐butyl) 3f , and 7‐phenyl 3g substituted 3‐chloro‐3,4‐dihydro‐l‐hydroxycarbostyrils. The various 4‐substituted α‐chloro‐β‐(2‐nitrophenyl)propionic acids 2c‐q were synthesized by reacting the in situ diazotized salts of the appropriate 4‐substituted‐2‐nitroanilines in aqueous acetone with acrylic acid in the presence of cuprous chloride and hydrochloric acid. All compounds prepared in this study were characterized by microanalytical and ir and nmr spectral data.