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ROUTES TO 1,3,4 – OXADIAZOL-2(3H)-ONES

Madaram, Karunakar Reddy
http://rave.ohiolink.edu/etdc/view?acc_num=wright1464279310

Abstract Details

, Master of Science (MS), Wright State University, Chemistry.
Various 1,3,4-oxadiazol-2(3H)-ones were synthesized by reaction of the bromocarbonylhydrazine salt(35) obtained from treatment of 4-bromo-3-phenylsydnone(34) with HCl with the corresponding acid chlorides in DME. The structures were confirmed by their physical, analytical and spectral data (IR, GC/MS, 1H and 13C NMR and CHN analysis). In general these compounds were synthesized in good to excellent yields and it is planned to continue exploration of their chemical behavior as a guide to their potential antimicrobial activity. As an initial approach to the synthesis of the desired 1,3,4-oxadiazol-2(3H)-ones, the starting material, 3-phenylsydnone, was prepared in 2 steps from commercially available N-phenylglycine in good overall yield. This sydnone was then converted into the versatile intermediate, 4-bromo-3-phenylsydnone. The latter was then converted by treatment with hydrochloric acid into the bromocarbonylhydrazine salt(35), which served as a key synthon for the preparation of a wide variety of 3,5-disubstituted oxadiazolinones. With respect to the cyclization step, the bromocarbonylhydrazine salt(35) was treated with an acid chloride (alkyl version) in DME and simple work-up with ice water / extraction resulted in a facile, high yield approach to the target oxadiazolinone. However, with aryl acid chlorides the use of a subsequent base treatment was needed to remove unreacted acid chloride and provide good yields of the corresponding oxadiazolinones. With a successful avenue in hand, attempts were made to optimize the yields of the desired 1,3,4-oxadiazol-2(3H)-ones by changing several parameters such as the amount of acid chloride, the reaction temperature and the reaction time. The optimized approach was then used for the successful preparation of a number of oxadiazolinones, including one new compound, viz. 5-(3-bromophenyl)-3-phenyl-1, 3, 4-oxadiazol-2(3H)-one (49), which was obtained in 60% yield.
Kenneth Turnbull, Ph.D. (Advisor)
Eric Fossum, Ph.D. (Committee Member)
William Feld, Ph.D. (Committee Member)
68 p.
Chemistry
chemistry

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Citations

  • Madaram, K. R. (2016). ROUTES TO 1,3,4 – OXADIAZOL-2(3H)-ONES [Master's thesis, Wright State University]. OhioLINK Electronic Theses and Dissertations Center. http://rave.ohiolink.edu/etdc/view?acc_num=wright1464279310

    APA Style (7th edition)

  • Madaram, Karunakar Reddy. ROUTES TO 1,3,4 – OXADIAZOL-2(3H)-ONES . 2016. Wright State University, Master's thesis. OhioLINK Electronic Theses and Dissertations Center, http://rave.ohiolink.edu/etdc/view?acc_num=wright1464279310.

    MLA Style (8th edition)

  • Madaram, Karunakar Reddy. "ROUTES TO 1,3,4 – OXADIAZOL-2(3H)-ONES ." Master's thesis, Wright State University, 2016. http://rave.ohiolink.edu/etdc/view?acc_num=wright1464279310

    Chicago Manual of Style (17th edition)

wright1464279310
511
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This open access ETD is published by Wright State University and OhioLINK.