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Synthesis of 5-methyl-3-phenyl-1,3,4-oxadiazol-2(3H)-one derivatives by electrophilic aromatic substitution

Conde, Amanda Solis
http://rave.ohiolink.edu/etdc/view?acc_num=wright1547584724393162

Abstract Details

2018, Master of Science (MS), Wright State University, Chemistry.
An important research element in the Turnbull laboratory has been the one-pot synthesis of 5-methyl-3-phenyl-1,3,4-oxadiazol-2(3H)-one from sydnone. The present study reexamined the reaction of 5-methyl-3-phenyl-1,3,4-oxadiazol-2(3H)-one with electrophiles and optimized methods for synthesis of oxadiazolinone derivatives. Further the oxadiazolinone derivatives were reacted with electrophiles to better comprehend the donating ability of the oxadiazolinone ring system in general with the expectation that the oxadiazolinone ring system is a slightly donating system. Additionally, when the structure assignment of the oxadiazolinone derivative was ambiguous, the corresponding oxadiazolinone or it’s isomer was synthesized from the appropriate sydnone to validate or refute the suggested structure. The results of the present study showed the reproducibility of experiments done by previous interns in the Turnbull laboratory. The procedure for nitration of 5-methyl-3-phenyl-1,3,4-oxadiazol-2(3H)-one could be optimized. Extension of nitration to para substituted oxadiazolinones resulted in di-substituted derivatives. Through these nitration studies, the oxadiazolinone ring system is shown to be a moderate donor.
Kenneth Turnbull, Ph.D. (Advisor)
Eric Fossum, Ph.D. (Committee Member)
Daniel Ketcha, Ph.D. (Committee Member)
147 p.
Chemistry; Organic Chemistry
5-methyl-3-phenyl-1,3,4-oxadiazol-2 3H-one; oxadiazolinone derivatives

Recommended Citations

Citations

  • Conde, A. S. (2018). Synthesis of 5-methyl-3-phenyl-1,3,4-oxadiazol-2(3H)-one derivatives by electrophilic aromatic substitution [Master's thesis, Wright State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=wright1547584724393162

    APA Style (7th edition)

  • Conde, Amanda. Synthesis of 5-methyl-3-phenyl-1,3,4-oxadiazol-2(3H)-one derivatives by electrophilic aromatic substitution. 2018. Wright State University, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=wright1547584724393162.

    MLA Style (8th edition)

  • Conde, Amanda. "Synthesis of 5-methyl-3-phenyl-1,3,4-oxadiazol-2(3H)-one derivatives by electrophilic aromatic substitution." Master's thesis, Wright State University, 2018. http://rave.ohiolink.edu/etdc/view?acc_num=wright1547584724393162

    Chicago Manual of Style (17th edition)

wright1547584724393162
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This open access ETD is published by Wright State University and OhioLINK.