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İkincil Enaminon Bileşiklerinin Suda Sentezi ve Karakterizasyonu

Yıl 2022, Cilt: 12 Sayı: 2, 216 - 222, 24.12.2022

Öz

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

Destekleyen Kurum

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Proje Numarası

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Kaynakça

  • 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
  • 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
  • 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
  • Greenhill, JV. 1977. Enaminones. Chem. Soc. Rev., 6:277-294. Doi: 10.1039/CS9770600277
  • 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
  • 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
  • Gungor, FS., Hancioglu, N., Anac, O. 2013. Reactions of enaminones with diazocarbonyl compounds. Helv. Chim. Acta, 96:488-493. Doi: 10.1002/hlca.201200233
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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

Synthesis and Characterization of Secondary Enaminone Compounds in Water

Yıl 2022, Cilt: 12 Sayı: 2, 216 - 222, 24.12.2022

Öz

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.

Proje Numarası

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Kaynakça

  • 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
  • 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
  • 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
  • Greenhill, JV. 1977. Enaminones. Chem. Soc. Rev., 6:277-294. Doi: 10.1039/CS9770600277
  • 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
  • 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
  • Gungor, FS., Hancioglu, N., Anac, O. 2013. Reactions of enaminones with diazocarbonyl compounds. Helv. Chim. Acta, 96:488-493. Doi: 10.1002/hlca.201200233
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
Toplam 23 adet kaynakça vardır.

Ayrıntılar

Birincil Dil Türkçe
Bölüm Araştırma Makaleleri
Yazarlar

Füsun Şeyma Güngör 0000-0003-0870-4048

Proje Numarası -
Yayımlanma Tarihi 24 Aralık 2022
Yayımlandığı Sayı Yıl 2022 Cilt: 12 Sayı: 2

Kaynak Göster

APA Güngör, F. Ş. (2022). İkincil Enaminon Bileşiklerinin Suda Sentezi ve Karakterizasyonu. Karaelmas Fen Ve Mühendislik Dergisi, 12(2), 216-222. https://doi.org/10.7212/karaelmasfen.1097171
AMA Güngör FŞ. İkincil Enaminon Bileşiklerinin Suda Sentezi ve Karakterizasyonu. Karaelmas Fen ve Mühendislik Dergisi. Aralık 2022;12(2):216-222. doi:10.7212/karaelmasfen.1097171
Chicago Güngör, Füsun Şeyma. “İkincil Enaminon Bileşiklerinin Suda Sentezi Ve Karakterizasyonu”. Karaelmas Fen Ve Mühendislik Dergisi 12, sy. 2 (Aralık 2022): 216-22. https://doi.org/10.7212/karaelmasfen.1097171.
EndNote Güngör FŞ (01 Aralık 2022) İkincil Enaminon Bileşiklerinin Suda Sentezi ve Karakterizasyonu. Karaelmas Fen ve Mühendislik Dergisi 12 2 216–222.
IEEE F. Ş. Güngör, “İkincil Enaminon Bileşiklerinin Suda Sentezi ve Karakterizasyonu”, Karaelmas Fen ve Mühendislik Dergisi, c. 12, sy. 2, ss. 216–222, 2022, doi: 10.7212/karaelmasfen.1097171.
ISNAD Güngör, Füsun Şeyma. “İkincil Enaminon Bileşiklerinin Suda Sentezi Ve Karakterizasyonu”. Karaelmas Fen ve Mühendislik Dergisi 12/2 (Aralık 2022), 216-222. https://doi.org/10.7212/karaelmasfen.1097171.
JAMA Güngör FŞ. İkincil Enaminon Bileşiklerinin Suda Sentezi ve Karakterizasyonu. Karaelmas Fen ve Mühendislik Dergisi. 2022;12:216–222.
MLA Güngör, Füsun Şeyma. “İkincil Enaminon Bileşiklerinin Suda Sentezi Ve Karakterizasyonu”. Karaelmas Fen Ve Mühendislik Dergisi, c. 12, sy. 2, 2022, ss. 216-22, doi:10.7212/karaelmasfen.1097171.
Vancouver Güngör FŞ. İkincil Enaminon Bileşiklerinin Suda Sentezi ve Karakterizasyonu. Karaelmas Fen ve Mühendislik Dergisi. 2022;12(2):216-22.