2002 addition reactions addition reactions O 0060 37 - 037 Conjugate Addition of Thiols and Malonates to Thiocinnamates under PTC Conditions. — Thiocinnamates (I) react chemoselectively with aryl thiols (II) and malonate (IV) to furnish the corresponding 1,4-adducts in mod- erate to good yield. However, analogous reaction using N-acetamidomalonate (VI) instead of malonate (IV) results in the rather unexpected formation of a functionalized pyrrolidinone via intramolecular cyclization of the parent adduct. — (MARZORATI, LILIANA; DE MATTOS, MARCOS CAR- LOS; WLADISLAW, BLANKA; DI VITTA, CLAUDIO; Synth. Commun. 32 (2002) 9, 1427-1435; Inst. Quim., Univ. Sao Paulo, 05599 Sao Paulo, Brazil; EN) 1

ChemInform Abstract: Conjugate Addition of Thiols and Malonates to Thiocinnamates under PTC Conditions

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Page 1: ChemInform Abstract: Conjugate Addition of Thiols and Malonates to Thiocinnamates under PTC Conditions

2002 addition reactions

addition reactionsO 0060

37 - 037Conjugate Addition of Thiols and Malonates to Thiocinnamates underPTC Conditions. — Thiocinnamates (I) react chemoselectively with arylthiols (II) and malonate (IV) to furnish the corresponding 1,4-adducts in mod-erate to good yield. However, analogous reaction using N-acetamidomalonate(VI) instead of malonate (IV) results in the rather unexpected formation ofa functionalized pyrrolidinone via intramolecular cyclization of the parentadduct. — (MARZORATI, LILIANA; DE MATTOS, MARCOS CAR-LOS; WLADISLAW, BLANKA; DI VITTA, CLAUDIO; Synth. Commun. 32(2002) 9, 1427-1435; Inst. Quim., Univ. Sao Paulo, 05599 Sao Paulo, Brazil; EN)