CONJUGATE ADDITION OF THIOLS AND MALONATES TO THIOCINNAMATES UNDER PTC CONDITIONS

ABSTRACT

Addition of thiols or diethylmalonate to thiocinnamate, under solid–liquid PTC conditions, afforded the corresponding 1,4-adducts in moderate to good yields. A 2-pyrrolidinone was obtained using diethyl N-acetamidomalonate as Michael donor, via intramolecular cyclization of the parent adduct.

Keywords:

• Thiocinnamates
• Conjugate addition
• Phase transfer catalysis
• Pyrrolidinone

ACKNOWLEDGMENTS

We are grateful to “Fundação de Amparo à Pesquisa do Estado de São Paulo—FAPESP” and “Conselho Nacional de Desenvolvimento Científico e Tecnológico—CNPq” for grants and financial support.