One-pot double annulations to confer diastereoselective spirooxindolepyrrolothiazoles

A novel four-component reaction in one pot as an atom-and step-economic process was developed to synthesize diastereoselective-ly spirooxindolepyrrolothiazoles through sequential N,S-acetalation of aldehydes with cysteine and decarboxylative [3 + 2] cycload-dition with olefinic oxindoles. High synthetic efficiency, operational simplification and reaction process economy using EtOH as solvent, and only releasing CO2 and H2O as side products confer this approach favorable in green chemistry metrics analysis.

Automated summary

A novel four-component reaction has been developed for the synthesis of diastereoselective-ly spirooxindolepyrrolothiazoles. The reaction involves sequential N,S-acetalation of aldehydes with cysteine and decarboxylative [3 + 2] cycloaddition with olefinic oxindoles. The use of EtOH as solvent and the release of only CO2 and H2O as side products make this approach favorable in green chemistry metrics analysis.