Resin-Bound (Succinimid-1-yloxycarbonylmethyl)triphenylphosphonium Ylide - A Synthon for Rapid Access to Diverse Heterocycles under Microwave Heating
作者:Bernd Henkel
DOI:10.1055/s-2008-1032046
日期:2008.2
The synthesis of a novel and versatile resin-bound (succinimid-1-yloxycarbonylmethyl)triphenylphosphonium ylide is described. The use of this resin to the synthesis of several diverse heterocycles, whilst allowing for ease of workup, is reported.
Disclosed is an aminopyrrolidine compound represented by the formula [I] or a pharmaceutically acceptable salt thereof. The compound or the salt is useful as a prophylactic/therapeutic agent for mode disorder such as depression, anxiety disorder, anorexia, cachexia, pain and drug dependence, whose action relies on the MC
4
receptor antagonistic effect.
In the first part of the present study, five substituted 4-hydroxyquinolin-2(1H)-ones (1-5) were prepared and then subjected to the reactions with various nucleophilic and electrophilic reagents including alkyl halides, dimethyl sulfate, bromine, anhydride acetic, and anilines to synthesize some new products (6-30). In the second part of this study, 6-chloro-4-hydroxyquinolin-2(1H)-one and/or 6,8-dichloro-4-hydroxyquinolin-2(1H)-one were employed in a catalyst-free, environmentally friendly, and simple procedure for the efficient synthesis of new derivatives (31-36) from one-pot three-component condensation with aryl-aldehydes and piperidine. The structures of the compounds were characterized by physical and spectral data.. KEYWORDS :4-Hydroxyquinolin-2(1H)-one, Alkylation, Aryl-amination, Methylation, Three-component condensation.