ACETYLENIC DIMERIZATION UNDER BASIC CONDITIONS
Journal Title: International Journal of Pharmacy and Pharmaceutical Sciences - Year 2015, Vol 7, Issue 8
Abstract
Objective: The lack of information concerning the pharmacological activity of amino acetylenic amide derivatives in which the cyclic amine is aziridine or azetidine promoted our interest to synthesize N-[4-(1-azeridinyl)-2-butynyl] pyrrolide-1,3-dione 4, N-[4-(1-azetidinyl)-2-butynyl] pyrrolidine-1,3-dione 5 and N-[4-(1-pyrrolidnyl)-2-butynyl]pyrrolide-1,3-dione 6.Methods: Melting points, IR, 1H-NMR 13CNMRspectra were measured.Results: Dimerization of 2-(prop-2-yn-1-yl) pyrrolidine-1,3-dione was generated rather than Mannich product, while using pyrrolidine as base in Mannich reaction generated the expected Mannich product. Rationalization for the mechanism of dimerization and Mannich adduct are discussed.Conclusion: Mannich reaction may afford the dimerization product of the acetylenic compounds rather than Mannich adduct.Â
Authors and Affiliations
Zuhair Muhi-eldeen, Elham Al-kaissi, Najah Al-muhtaseb
Keywords
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