ACETYLENIC DIMERIZATION UNDER BASIC CONDITIONS

Authors

  • Zuhair Muhi-eldeen Department of Medicinal Chemistry and Pharmacognosy, University of Petra, Amman, Jordan
  • Elham Al-kaissi Department of Pharmaceutics and Pharmaceutical Technology, University of Petra, Amman, Jordan
  • Najah Al-muhtaseb Department of Medicinal Chemistry and Pharmacognosy, University of Petra, Amman, Jordan

Keywords:

Acetylenic dimerization, Aminoactylenic derivative, Azetidine derivative, Aziridine derivative, Mannich reaction

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.


 

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Author Biography

Zuhair Muhi-eldeen, Department of Medicinal Chemistry and Pharmacognosy, University of Petra, Amman, Jordan

Dept. Medicinal Chemistry and Pharmacognocy

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Published

01-08-2015

How to Cite

Muhi-eldeen, Z., E. Al-kaissi, and N. Al-muhtaseb. “ACETYLENIC DIMERIZATION UNDER BASIC CONDITIONS”. International Journal of Pharmacy and Pharmaceutical Sciences, vol. 8, no. 8, Aug. 2015, pp. 290-3, https://mail.innovareacademics.in/journals/index.php/ijpps/article/view/6488.

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