Stereoselective and Triphenylphosphine-Catalyzed Synthesis of 2,2'-azanediyldifumarate and 2-benzoylfumarate: Synthesis of the Tekfidra drug derivatives
Subject Areas : شیمی آلی
Seyed Javad Hosseini
1
,
Safa Ali-Asgari
2
1 - Department of Chemistry, Shahrood Branch, Islamic Azad University, Shahrood, Iran
2 - Department of Chemistry, Shahrood Branch, Islamic Azad University, Shahrood, Iran
Keywords: 2, Triphenylphosphine, Dimethyl acetylenedicarboxylate, 2'-azanediyldifumarates, 2-benzoylfumarates,
Abstract :
The reaction between tri phenyl phosphine, dialkyl acetylene di carboxylate and ammonium acetate in acetonitrile under mild conditions leads to the production of 2,2'-azane diyl di fumarates with a good yield. Also the reaction between tri phenylphosphine, di methyl acetylene di carboxylate and benzaldehydes in di chloromethane under mild conditions leads to the production of 2-benzoylfumarate derivatives with a suitable yield. In both reactions, tri phenylphosphine, as a catalyst, produces a 1,3-di polar intermediate by nucleophilic attack on acetylenic carbon, and it is removed as a leaving group in the final stage of the reaction. Also, both reactions are stereoselective, and only one isomer was isolated among the possible stereoisomers. Synthesized compounds are important as derivatives of the Tekfidra drug (di methyl fumarate), which is used in the treatment of MS. The structures of the products were determined by 1HNMR, 13CNMR, IR, elemental analysis and single crystal X-ray diffraction data.
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