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Synthesis and Characterization of Enaminone Derivatives of Barbituric Acid

Year 2019, Volume: 9 Issue: 2, 993 - 1003, 01.06.2019
https://doi.org/10.21597/jist.442571

Abstract

In this study, four enaminones derived from barbituric acid were synthesized with the reaction of 5-formylbarbituric acid and selected primer amines with high yield. The structures of all

compounds were proved by using ATR-FTIR, 1H and 13C NMR spectroscopy. Also, 19F NMR spectroscopy was used for characterization of 2d. The obtained spectroscopic results have complied

with reported similar derivatives in literature.

Supporting Institution

Scientific Research Project Unit (BAP) of Aydın Adnan Menderes University

Project Number

FEF-17020

Thanks

This work has been supported financially by “Scientific Research Project Unit (BAP) of Aydın Adnan Menderes University” (Project No: FEF-17020).

References

  • Baldwin GA, Bevan J, Brough D, Ruth Ledder R, Freeman S, 2018. Synthesis and antibacterial activities of enamine derivatives of dehydroacetic acid. Medicinal Chemistry Research, 27: 884-889.
  • Castro-Alvarez A, Carneros H, Costa MA, Vilarrasa J, 2017. Computer-Aided Insight into the Relative Stability of Enamines. Synthesis, 49: 5285-5306.
  • Kumar P, Zainul O, Laughlin TS, 2018. Inexpensive multigram-scale synthesis of cyclic enamines and 3-N spirocyclopropyl systems. Organic & Biomolecular Chemistry, 16: 652-656.
  • Negri G, Kascheres C, Kascheres JA, 2004. Recent Development in Preparation Reactivity and Biological Activity of Enaminoketones and Enaminothiones and Their Utilization to Prepare Heterocyclic Compounds. Journal of Heterocyclic Chemistry, 41: 461- 491.
  • Elassar AA, El-Khair AA, 2003. Recent developments in the chemistry of enaminones. Tetrahedron, 59: 8463-8480.
  • Mahmudov K T, Kopylovich M N, Maharramov A M, Kurbanova M M, Gurbanov A V, Pombeiro A J L, 2014. Barbituric acid as a useful tool for the construction of coordination and supramolecular compounds. Coordination Chemistry Review, 265: 1-37.
  • Fırıncı E, Giziroglu E, Celepci D B, Söyleyici H C, Aygün M, 2017. Spiro copper(II)-metallacycles derived from 5-arylaminomethylene-barbituric acids: Synthesis and structural characterization. Journal of Molecular Structure, 1137: 113-118.
  • Neumann DM, Cammarata A, Backes G, Palmer GE, Jursic B S, 2014. Synthesis and antifungal activity of substituted 2,4,6-pyrimidinetrione carbaldehyde hydrazones. Bioorganic & Medicinal Chemistry, 22: 813-826.
  • Vidovic D, Findlater M, Cowley HA, 2007. A β-Diketiminate-Sopported Boron Dication. Journal of American Chemical Society, 129: 8436-8437.
  • Rauf A, Shahzad S, Bahda M, Yar M, Ahmed F, Hussain N, Akhtar MN, Khan A, Jonczyk J, 2015. Design and synthesis of new barbituric- and thiobarbituric acid derivatives as potent urease inhibitors: Structure activity relationship and molecular modeling studies. Bioorganic & Medicinal Chemistry, 23: 6049-6058.

Barbitürik Asitin Enaminon Türevlerinin Sentezi ve Karakterizasyonu

Year 2019, Volume: 9 Issue: 2, 993 - 1003, 01.06.2019
https://doi.org/10.21597/jist.442571

Abstract

Bu çalışmada barbitürik asitten türeyen dört enaminon türevi 5-formilbarbitürik asit ve seçilen birincil aminlerin reaksiyonu ile yüksek verimle sentezlenmiştir. Sentezlenen bütün bileşiklerin

yapıları ATR-FTIR, 1H ve 13C NMR spektroskopileri kullanılarak kanıtlanmıştır. Bileşik 2d’nin yapısal karakterizasyonun da ayrıca 19F NMR spektroskopisi kullanılmıştır. Elde edilen spektroskopik

sonuçlar literatürdeki rapor edilmiş benzer türevler ile uyumludur.

Project Number

FEF-17020

References

  • Baldwin GA, Bevan J, Brough D, Ruth Ledder R, Freeman S, 2018. Synthesis and antibacterial activities of enamine derivatives of dehydroacetic acid. Medicinal Chemistry Research, 27: 884-889.
  • Castro-Alvarez A, Carneros H, Costa MA, Vilarrasa J, 2017. Computer-Aided Insight into the Relative Stability of Enamines. Synthesis, 49: 5285-5306.
  • Kumar P, Zainul O, Laughlin TS, 2018. Inexpensive multigram-scale synthesis of cyclic enamines and 3-N spirocyclopropyl systems. Organic & Biomolecular Chemistry, 16: 652-656.
  • Negri G, Kascheres C, Kascheres JA, 2004. Recent Development in Preparation Reactivity and Biological Activity of Enaminoketones and Enaminothiones and Their Utilization to Prepare Heterocyclic Compounds. Journal of Heterocyclic Chemistry, 41: 461- 491.
  • Elassar AA, El-Khair AA, 2003. Recent developments in the chemistry of enaminones. Tetrahedron, 59: 8463-8480.
  • Mahmudov K T, Kopylovich M N, Maharramov A M, Kurbanova M M, Gurbanov A V, Pombeiro A J L, 2014. Barbituric acid as a useful tool for the construction of coordination and supramolecular compounds. Coordination Chemistry Review, 265: 1-37.
  • Fırıncı E, Giziroglu E, Celepci D B, Söyleyici H C, Aygün M, 2017. Spiro copper(II)-metallacycles derived from 5-arylaminomethylene-barbituric acids: Synthesis and structural characterization. Journal of Molecular Structure, 1137: 113-118.
  • Neumann DM, Cammarata A, Backes G, Palmer GE, Jursic B S, 2014. Synthesis and antifungal activity of substituted 2,4,6-pyrimidinetrione carbaldehyde hydrazones. Bioorganic & Medicinal Chemistry, 22: 813-826.
  • Vidovic D, Findlater M, Cowley HA, 2007. A β-Diketiminate-Sopported Boron Dication. Journal of American Chemical Society, 129: 8436-8437.
  • Rauf A, Shahzad S, Bahda M, Yar M, Ahmed F, Hussain N, Akhtar MN, Khan A, Jonczyk J, 2015. Design and synthesis of new barbituric- and thiobarbituric acid derivatives as potent urease inhibitors: Structure activity relationship and molecular modeling studies. Bioorganic & Medicinal Chemistry, 23: 6049-6058.
There are 10 citations in total.

Details

Primary Language English
Subjects Chemical Engineering
Journal Section Kimya / Chemistry
Authors

Erkan Fırıncı 0000-0003-0741-9608

Project Number FEF-17020
Publication Date June 1, 2019
Submission Date July 11, 2018
Acceptance Date December 7, 2018
Published in Issue Year 2019 Volume: 9 Issue: 2

Cite

APA Fırıncı, E. (2019). Synthesis and Characterization of Enaminone Derivatives of Barbituric Acid. Journal of the Institute of Science and Technology, 9(2), 993-1003. https://doi.org/10.21597/jist.442571
AMA Fırıncı E. Synthesis and Characterization of Enaminone Derivatives of Barbituric Acid. J. Inst. Sci. and Tech. June 2019;9(2):993-1003. doi:10.21597/jist.442571
Chicago Fırıncı, Erkan. “Synthesis and Characterization of Enaminone Derivatives of Barbituric Acid”. Journal of the Institute of Science and Technology 9, no. 2 (June 2019): 993-1003. https://doi.org/10.21597/jist.442571.
EndNote Fırıncı E (June 1, 2019) Synthesis and Characterization of Enaminone Derivatives of Barbituric Acid. Journal of the Institute of Science and Technology 9 2 993–1003.
IEEE E. Fırıncı, “Synthesis and Characterization of Enaminone Derivatives of Barbituric Acid”, J. Inst. Sci. and Tech., vol. 9, no. 2, pp. 993–1003, 2019, doi: 10.21597/jist.442571.
ISNAD Fırıncı, Erkan. “Synthesis and Characterization of Enaminone Derivatives of Barbituric Acid”. Journal of the Institute of Science and Technology 9/2 (June 2019), 993-1003. https://doi.org/10.21597/jist.442571.
JAMA Fırıncı E. Synthesis and Characterization of Enaminone Derivatives of Barbituric Acid. J. Inst. Sci. and Tech. 2019;9:993–1003.
MLA Fırıncı, Erkan. “Synthesis and Characterization of Enaminone Derivatives of Barbituric Acid”. Journal of the Institute of Science and Technology, vol. 9, no. 2, 2019, pp. 993-1003, doi:10.21597/jist.442571.
Vancouver Fırıncı E. Synthesis and Characterization of Enaminone Derivatives of Barbituric Acid. J. Inst. Sci. and Tech. 2019;9(2):993-1003.