Microwave-Assisted Three-Component Synthesis of Some Novel 1-Alkyl-1H-indole-2,3-dione 3-(O-Alkyl­oxime) Derivatives as Potential Chemotherapeutic Agents

✍ Scribed by Mohammad Navid Soltani Rad; Ali Khalafi-Nezhad; Somayeh Babamohammadi; Somayeh Behrouz

• Publisher: John Wiley and Sons
• Year: 2010
• Tongue: German
• Weight: 236 KB
• Volume: 93
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.201000104

✦ Synopsis

A convenient and efficient method for a one-pot conversion of N-alkylisatins to N-alkylisatin Oalkyloximes 7a -7n as potential chemotherapeutic agents is described (Scheme) (isatin ¼ 1H-indole-2,3dione). In this method, the microwave-assisted three-component reaction of N-alkylisatins 8, hydroxylamine hydrochloride, and diverse alkyl halides in the presence of K 2 CO 3 and Bu 4 NBr furnishes the corresponding N-alkylisatin O-alkyloximes under solvent-free condition in short times (2 -10 min) and good to excellent yields (62 -83%). The O-alkylation of in situ generated isatin oximes with alkyl halides was achieved regioselectively, and (Z)-O-alkyloximes were produced dominantly. PM3 Semi-empirical quantum-mechanic calculations were performed to rationalize the evidences, and the calculations indicated a lower heat of formation for the (Z)-O-alkyloximes.