Öz
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.
Anahtar Kelimeler
Barbituric acid Enaminone Condensation reaction Spectroscopy
Destekleyen Kurum
Scientific Research Project Unit (BAP) of Aydın Adnan Menderes University
Proje Numarası
FEF-17020
Teşekkür
This work has been supported financially by “Scientific Research Project Unit (BAP) of Aydın Adnan Menderes University” (Project No: FEF-17020).
Kaynakça
- 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.
Öz
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.
Anahtar Kelimeler
Barbitürik asit Enaminon Kondenzasyon reaksiyonu Spektroskopi
Proje Numarası
FEF-17020
Kaynakça
- 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.
Ayrıntılar
| Birincil Dil | İngilizce |
|---|---|
| Konular | Kimya Mühendisliği |
| Bölüm | Kimya / Chemistry |
| Yazarlar | |
| Proje Numarası | FEF-17020 |
| Yayımlanma Tarihi | 1 Haziran 2019 |
| Gönderilme Tarihi | 11 Temmuz 2018 |
| Kabul Tarihi | 7 Aralık 2018 |
| Yayımlandığı Sayı | Yıl 2019 |