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The Attempted Synthesis of Carba-Nicotinic Acid Mononucleotide Methyl Ester using the Zincke Reaction

Zhao, Peng
http://rave.ohiolink.edu/etdc/view?acc_num=mco1488576282701401

Abstract Details

2017, Master of Science (MS), University of Toledo, Medicinal Chemistry.
According to the retrosynthetic analysis, the carba-nicotinic acid mononucleotide methyl ester can be synthesized from a nucleoside made using a primary amine and a Zincke salt by the Zincke reaction. The primary amine which was the cyclopentane analog of 1-aminoribose was synthesized following the procedure described by Cermak and Vince in 1981 starting from the Vince lactam. The pyridinium part was synthesized as a Zincke salt. However carba-nicotinic acid mononucleotide methyl ester cannot be synthesized using this procedure due to the unanticipated high reactivity of the nicotinic acid esters with primary amine during the Zincke reaction. We found that pyridinium-3-carboxylic esters reacted rapidly with amines resulting in the formation of amids. A series of Zincke reaction were performed to study the Zincke reaction. Even the most sterically hindered protecting group tert-butyl ester could not prevent the formation of nicotinamide.
James Slama, Ph.D. (Committee Chair)
Viranga Tillekeratne, D.Phil. (Committee Member)
Isaac Schiefer, Ph.D. (Committee Member)
Chemistry; Pharmacy Sciences

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Citations

  • Zhao, P. (2017). The Attempted Synthesis of Carba-Nicotinic Acid Mononucleotide Methyl Ester using the Zincke Reaction [Master's thesis, University of Toledo]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=mco1488576282701401

    APA Style (7th edition)

  • Zhao, Peng. The Attempted Synthesis of Carba-Nicotinic Acid Mononucleotide Methyl Ester using the Zincke Reaction. 2017. University of Toledo, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=mco1488576282701401.

    MLA Style (8th edition)

  • Zhao, Peng. "The Attempted Synthesis of Carba-Nicotinic Acid Mononucleotide Methyl Ester using the Zincke Reaction." Master's thesis, University of Toledo, 2017. http://rave.ohiolink.edu/etdc/view?acc_num=mco1488576282701401

    Chicago Manual of Style (17th edition)

mco1488576282701401
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© 2017, some rights reserved.Creative Commons License The Attempted Synthesis of Carba-Nicotinic Acid Mononucleotide Methyl Ester using the Zincke Reaction by Peng Zhao is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 3.0 Unported License. Based on a work at etd.ohiolink.edu.
This open access ETD is published by University of Toledo Health Science Campus and OhioLINK.