Journals / Karaelmas Fen ve Mühendislik Dergisi / 2022 / Cilt: 12 Sayı: 2

Synthesis and Characterization of Secondary Enaminone Compounds in Water

İkincil Enaminon Bileşiklerinin Suda Sentezi ve Karakterizasyonu

Füsun Şeyma Güngör(ISTANBUL TECHNICAL UNIVERSITY)0000-0003-0870-4048
Pages
216–222
Publication Date
2022-12-24
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AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

Performing the reaction in water resulted in increased reaction yield.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:Enaminon compounds have a wide range of applications in synthetic organic chemistry.
📊
Key Findings & Data:In this study, secondary enaminone compounds were synthesized with high yield and in a short time from the reactions of tertiary enaminoketone and enaminoester compounds and aromatic amines in water with FeCl3.6H2O as a catalyst.
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Conclusion & Impact:Performing the reaction in water resulted in increased reaction yield.
🔬Design:Araştırma Makalesi
📍Scope:Comprehensive Sample
⚙️Variables:Enaminon · Katalizör · Kondenzasyon

Abstract

Enaminon compounds have a wide range of applications in synthetic organic chemistry. Especially in recent years, many studies have been conducted on organic syntheses containing enaminone and their catalytic applications. In this study, secondary enaminone compounds were synthesized with high yield and in a short time from the reactions of tertiary enaminoketone and enaminoester compounds and aromatic amines in water with FeCl3.6H2O as a catalyst. In the method, the reactions were carried out in the water and an organic solvent was not needed. Performing the reaction in water resulted in increased reaction yield.

Özet

Enaminon bileşikleri, sentetik organik kimyada çok geniş bir yelpazede uygulama alanına sahiptir. Özellikle son yıllarda , enaminona içeren organik sentezler ve onların katalitik uygulamalara yönelik araştırmalar çokça yapılmıştır. Bu çalışmada da üçüncül enaminoketon ve enaminoester bileşikleri ile aromatik aminlerin FeCl3.6H2O katalizörlüğünde su içinde gerçekleştirilen tepkimelerinden yüksek verimle ve kısa sürede ikincil enaminon bileşikleri sentezlenmiştir. Yöntemde tepkimeler su içinde gerçekleştirilmiş olup bir organik çözücüye ihtiyaç duyulmamıştır. Tepkimenin su içinde gerçekleştirilmesi tepkime veriminin artmasına neden olmuştur

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Cite This Article

Güngör, F. Ş. (2022). Synthesis and Characterization of Secondary Enaminone Compounds in Water. Karaelmas Fen ve Mühendislik Dergisi, Cilt: 12 Sayı: 2, 216–222. https://doi.org/10.7212/karaelmasfen.1097171

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References (23)

  1. Al-Omran, A-ZA., Elassar, A., El-Khair, A. 2001. Synthesis of condensed heteroaromatics: a novel synthesis of aminoquinolizinone derivatives as anti-HIV agents. Tetrahedron, 57:10163-10170. Doi: 10.1016/S0040-4020(01)01039-0
  2. Al-Omran, F., El-Khair, AA., Elnagdi, MH. 1998. Studies with polyfunctionally substituted heteroaromatics: a novel synthesis of substituted 4,8-diaminoisoquinolines as potential antiparasitic agents. J. Chem. Res. (S), 798-799. Doi: 10.1039/A804639E
  3. Caubere, C., Caubere, P., Ianelli, S., Nardelli, M., Jamart-Gregoire, B. 1994. Aggregative activation and heterocyclic chemistry I complex bases promoted arynic cyclisation of imine or enaminoketones; regiochemical synthesis of indoles. Tetrahedron, 50:11903-11920. Doi: 10.1016/S0040-4020(01)89304-2
  4. Greenhill, JV. 1977. Enaminones. Chem. Soc. Rev., 6:277-294. Doi: 10.1039/CS9770600277
  5. Gungor, FS., Anac, O., Sezer, O. 2007. Observations on the copper(II) catalyzed reactions of enaminones and dimethyl diazomalonate. Tetrahedron Lett., 48:4883-4886. Doi: 10.1016/j.tetlet.2007.05.063
  6. Gungor, FS., Anac, O., Sezer, O. 2011. Synthesis of the naphthalenone, dihydroquinoline, and dihydrofuran derivatives. Helv. Chim. Acta, 94:1115-1129. Doi: 10.1002/hlca.201000386
  7. Gungor, FS., Hancioglu, N., Anac, O. 2013. Reactions of enaminones with diazocarbonyl compounds. Helv. Chim. Acta, 96:488-493. Doi: 10.1002/hlca.201200233
  8. Hegde, SG., Jones, CR. 1993. Synthesis of 1,6-dihydro-5-hydroxy-6-oxo-3-(trifluoromethyl)-4-pyridazinecarboxylates. J. Heterocycl. Chem., 30:1501-1508. Doi: 10.1002/jhet.5570300607
  9. Huisgen, R., Herbig, K., Siegel, K., Huber, H. 1966. Die addukte primarer und sekundarer amine an carbonester der acetylenreihe und ihre konfiguration. Chem. Ber., 99:2526-2545. Doi: 10.1002/cber.19660990820
  10. Kascheres, CM. 2003. The chemistry of enaminones, diazocarbonyls and small rings: our contribution. J. Braz. Chem. Soc., 14:945-969. Doi: 10.1590/S0103-50532003000600012
  11. Liu, Y., Zhou, R., Wan, J-P. 2013. Water-promoted synthesis of enaminones: mechanism investigation and application in multicomponent reactions. Synth. Commun., 43:2475-2483. Doi: 10.1080/00397911.2012.715712
  12. Lue, P., Greenhill, JV. 1997. Enaminones in heterocyclic synthesis. Adv. Heterocycl. Chem. Alan Katritzky [ed], e-book, Academic press, 67, pp-207-343. ISBN: 9780080576541
  13. Reidlinger, C. Dworczak, R., Junk, H. 1998. Cyanoacetophenone as a synthon for 1,4,5-substituted pyrazoles. Monatsh. Chem., 129:1207-1211. Doi: 10.1007/PL00010132
  14. Reis, LV., Lobo, AM., Prabhakar, S. 1994. Enehydroxylamines as versatile compounds in 3,3-sigmatropic rearrangements. Tetrahedron Lett., 35:2747-2750. Doi: 10.1016/S0040-4039(00)77022-5
  15. San Martin, R., de Marigorta, EM., Dominguez, E. 1994. A convenient alternative route to β-aminoketones. Tetrahedron, 50:2255-2264. Doi: 10.1016/S0040-4020(01)85083-3
  16. Schuda, PF., Ebner, CB., Morgan, TM. 1986. The synthesis of mannich bases from ketones and esters via enaminones. Tetrahedron Lett., 27:2567-2570. Doi: 10.1016/S0040-4039(00)84586-4
  17. Selic, L., Grdadolnik, SG., Stanovnik, B. 1997. Methyl and phenylmethyl 2-acetyl-3-{[2-(dimethylamino)-1-(methoxycarbonyl)ethenyl]amino}prop-2-enoate in the synthesis of heterocyclic systems: preparation of 3-amino-4H-[1,2-a]pyrimidin-4-ones. Helv. Chim. Acta, 80:2418-2425. Doi: 10.1002/hlca.19970800811
  18. Svete, J., Aljaz-Rozic, M., Stanovnik, B 1997. 2-Benzoyl-2-ethoxycarbonylvinyl-1 and 2-benzoylamino-2-methoxy-carbonylvinyl-1 as N-protecting groups in peptide synthesis. Their application in the synthesis of dehydropeptide derivatives containing N-terminal 3-heteroarylamino-2,3-dehydroalanine. J. Heterocycl. Chem., 34:177-193. Doi: 10.1002/jhet.5570340128
  19. Thorwirth, R., Stolle, A. 2011. Solvent-free synthesis of enamines from alkyl esters of propiolic or but-2-yne dicarboxylic acid in a ball mill. Synlett, 2200–2202. Doi: 10.1055/s-0030-1261179
  20. Um, I-H., Lee, E-J., Seok, J-A., Kim, KH. 2005. The α-effect in reactions of sp-hybridized carbon atom: Michael type reactions of 1-aryl-2-propyn-1-ones with primary amines. J. Org. Chem., 70:7530–2536. Doi: 10.1021/jo050624t
  21. Yang, J., Wang, C., Xie, X., Li, H., Li, Y. 2010. Acid-catalyzed cascade reactions enaminones with aldehydes: C-H functionalization to afford 1,4-dihydropyridines. Eur. J. Org. Chem., 4189-4193. Doi: 10.1002/ejoc.201000607
  22. Zhang, M., Abdukader, A., Fu, Y., Zhu, C. 2012. Efficient synthesis of β-enaminones and β-enaminoesters catalyzed by gold (I)/silver (I) under solvent-free conditions. Molecules, 17:2812-2822. Doi: 10.3390/molecules17032812
  23. Zupancic, S., Svete, J., Stanovnik, B. 2001. Synthesis and transformations of alkyl 1,5-bis(dimethylamino)-3-oxopenta-1,4-diene-2,4-dicarboxylates. A simple synthesis of dialkyl 1-substituted 4-oxo-1,4-dihydropyridine3,5-dicarboxylates. Heterocycl., 53:2033-2042. Doi: 10.3987/COM-00-8944