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Synthesis and Identification of New Chiral Compounds Containing Azomethine Ylide Core

Year 2017, Volume: 38 Issue: 2, 264 - 274, 24.04.2017

Mustafa Kemal Gümüş

https://doi.org/10.17776/cumuscij.297283
Cited By: 1

Abstract

In
the present study, 14 new dialkyl
(2-oxo-2-{[(1S)-1-phenylethyl]amino}ethyl)dithioimidocarbonate and dialkyl
(2-oxo-2-{[(1SR)-1-phenylethyl]amino}ethyl)dithioimidocarbonate (4a-n) chiral
compuonds were synthesized starting from glycine salts (1). These compounds
contain the azomethine ylide core, which is used as 1,3-dipole reactant in
1,3-dipolar cycloaddition reactions. Furthermore, the synthesized azomethine
compounds contain a chiral amide function as a substituent. These compounds
were characterized by different spectroscopic techniques (IR, 1H
NMR, 13C NMR ve COSY NMR).

Keywords

azomethine ylide chiral glycine salt Amide function 1 3-dipolar cycloaddition glycine salt

References

  • [1]. Carruthers, W. Cycloaddition Reactions in Organic Synthesis (Vol. 8). Pergamon: Oxford, 1990; 274-284.
  • [2]. Gothelf, K. V. Asymmetric metal-catalyzed 1,3-dipolar cycloaddition reactions. Cycloaddition reactions in organic synthesis. John Wiley & Sons, New York, 2001; 211-245.
  • [3]. Huisgen, R. 1,3‐Dipolar Cycloadditions. Past and Future, Angewandte Chemie International Edition, 1963; 2(10), 565-598.
  • [4]. Harwood, L. M., & Vickers, R. J. Azomethine ylides. Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, Wiley: New York, Chichester. 2002; 169-253.
  • [5]. Doğan, Ö., Koyuncu, H., & Kanışkan, Ü. Lewis acid catalyzed 1,3-dipolar cycloadditon reactions of stabilized azomethine ylides. Turkish Journal of Chemistry, 2001; 25(3), 365-371.
  • [6]. Georgiou, D., Toutountzoglou, V., Muir, K. W., Hadjipavlou-Litina, D., & Elemes, Y. Synthesis of sulfur containing dihydropyrrolo derivatives and their biological evaluation as antioxidants. Bioorganic & Medicinal Chemistry, 2012; 20(17), 5103-5109.
  • [7]. Oikonomou, K., Georgiou, D., Katsamakas, S., Hadjipavlou Litina, D., & Elemes, Y. Sulfanyl 5H-dihydropyrrole derivatives via 1,3-dipolar cycloaddition, their further chemical manipulation and antioxidant activity. Arkivoc, 2015; 16, 214-231.
  • [8]. Boukouvala, M. C., Kavallieratos, N. G., Athanassiou, C. G., Losic, D., Hadjiarapoglou, L. P., & Elemes, Y. Laboratory evaluation of five novel pyrrole derivatives as grain protectants against Tribolium confusum and Ephestia kuehniella larvae. Journal of Pest Science, 2017, Volume 90, Issue 2, pp 569–585.
  • [9]. Ioannou, E., Hirsch, A., & Elemes, Y. Sulfur-containing dihydro-pyrrolo [60] fullerene derivatives via 1,3-dipolar cycloadditions of glycine imine esters to C60. Tetrahedron, 2007; 63(30), 7070-7076.
  • [10]. Naxakis, G., Sofou, P., & Elemes, Y. Synthesis of Novel 3, 4‐Dihydro‐2 H‐pyrrolo[60]fullerene Derivatives Bearing an Alkylsulfanyl Substituent. Fullerenes, Nanotubes and Carbon Nanostructures,Taylor & Francis; 2004; Vol. 12, No. 4, pp. 781–788.
  • [11]. Kohn, H., Sawhney, K. N., Bardel, P., Robertson, D. W., & Leander, J. D. Synthesis and anticonvulsant activities of alpha-heterocyclic alpha-acetamido-N-benzylacetamide derivatives. Journal of Medicinal Chemistry, 1993; 36(22), 3350-3360.
  • [12]. Kohn, H. L., Salomé, C., Park, K. D., & Salomé-Grosjean, E. N-benzylamide substituted derivatives of 2-(acylamido)acetic acid and 2-(acylamido)propionic acids: potent neurological agents. U.S. Patent and Trademark Office, Washington, DC; 2015; U.S. Patent No. 8,933,065 . [13]. King, A. M., Yang, X. F., Wang, Y. Y., Dustrude, E. T., Barbosa, C., Due, M. R., Piekarz, A. D., Wilson, S. M., White, F. A., Salome, C., Cummins, T. R., Khanna, R., Kohn, H., Identification of the Benzyloxyphenyl Pharmacophore: A Structural Unit That Promotes Sodium Channel Slow Inactivation. ACS Chemical Neuroscience 2012; 3 (12), 1037-1049.
  • [14]. Park, K. D., Yang, X. F., Dustrude, E. T., Wang, Y., Ripsch, M. S., White, F. A., & Kohn, H. Chimeric Agents Derived from the Functionalized Amino Acid, Lacosamide, and the α-Aminoamide, Safinamide: Evaluation of Their Inhibitory Actions on Voltage-Gated Sodium Channels, and Antiseizure and Antinociception Activities and Comparison with Lacosamide and Safinamide. ACS Chemical Neuroscience, 2014; 6(2), 316-330.
  • [15]. Hoppe, D., Beckmann, L. Selective Monoalkylation and Dialkylatıon of N-[Bis(Alkylthio)Methylene]Glycine Ethyl-Ester for Synthesis of Higher and Alpha-Branched Alpha-Amino-Acids. Liebigs Annalen der Chemie 1979; Issue: 12, p2066-2075.

Azometin Yilür Çekirdeği İçeren Yeni Kiral Bileşiklerin Sentezi ve Yapılarının Aydınlatılması

Year 2017, Volume: 38 Issue: 2, 264 - 274, 24.04.2017

Mustafa Kemal Gümüş

https://doi.org/10.17776/cumuscij.297283
Cited By: 1

Abstract

Bu
çalışmada 14 adet kiral yapıda yeni dialkil
(2-okso-2-{[(1S)-1-feniletil]amino}etil) ditiyoimidokarbonat ve
(2-okso-2-{[(1R)-1-feniletil]amino}etil)ditiyoimidokarbonat bileşiği (4a-n)
glisin tuzlarından (1) başlanılarak sentezlenmiştir. Bu bileşikler 1,3-dipolar
siklokatılma tepkimelerinde 1,3-dipol reaktifi olarak kullanılan azometin yilür
çekirdeği içermektedir. Ayrıca sentezlenen azometin yilür bileşikleri
substituent olarak kiral bir amit fonksiyonu da içermektedir. Bu bileşiklerin
yapıları farklı spektroskopik yöntemler (IR, 1H NMR, 13C
NMR ve COSY NMR) kullanılarak karakterize edilmiştir.

Keywords

amit fonksiyonu azometin yilür 1 3-dipolar siklokatılma glisin tuzu kiral

References

  • [1]. Carruthers, W. Cycloaddition Reactions in Organic Synthesis (Vol. 8). Pergamon: Oxford, 1990; 274-284.
  • [2]. Gothelf, K. V. Asymmetric metal-catalyzed 1,3-dipolar cycloaddition reactions. Cycloaddition reactions in organic synthesis. John Wiley & Sons, New York, 2001; 211-245.
  • [3]. Huisgen, R. 1,3‐Dipolar Cycloadditions. Past and Future, Angewandte Chemie International Edition, 1963; 2(10), 565-598.
  • [4]. Harwood, L. M., & Vickers, R. J. Azomethine ylides. Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, Wiley: New York, Chichester. 2002; 169-253.
  • [5]. Doğan, Ö., Koyuncu, H., & Kanışkan, Ü. Lewis acid catalyzed 1,3-dipolar cycloadditon reactions of stabilized azomethine ylides. Turkish Journal of Chemistry, 2001; 25(3), 365-371.
  • [6]. Georgiou, D., Toutountzoglou, V., Muir, K. W., Hadjipavlou-Litina, D., & Elemes, Y. Synthesis of sulfur containing dihydropyrrolo derivatives and their biological evaluation as antioxidants. Bioorganic & Medicinal Chemistry, 2012; 20(17), 5103-5109.
  • [7]. Oikonomou, K., Georgiou, D., Katsamakas, S., Hadjipavlou Litina, D., & Elemes, Y. Sulfanyl 5H-dihydropyrrole derivatives via 1,3-dipolar cycloaddition, their further chemical manipulation and antioxidant activity. Arkivoc, 2015; 16, 214-231.
  • [8]. Boukouvala, M. C., Kavallieratos, N. G., Athanassiou, C. G., Losic, D., Hadjiarapoglou, L. P., & Elemes, Y. Laboratory evaluation of five novel pyrrole derivatives as grain protectants against Tribolium confusum and Ephestia kuehniella larvae. Journal of Pest Science, 2017, Volume 90, Issue 2, pp 569–585.
  • [9]. Ioannou, E., Hirsch, A., & Elemes, Y. Sulfur-containing dihydro-pyrrolo [60] fullerene derivatives via 1,3-dipolar cycloadditions of glycine imine esters to C60. Tetrahedron, 2007; 63(30), 7070-7076.
  • [10]. Naxakis, G., Sofou, P., & Elemes, Y. Synthesis of Novel 3, 4‐Dihydro‐2 H‐pyrrolo[60]fullerene Derivatives Bearing an Alkylsulfanyl Substituent. Fullerenes, Nanotubes and Carbon Nanostructures,Taylor & Francis; 2004; Vol. 12, No. 4, pp. 781–788.
  • [11]. Kohn, H., Sawhney, K. N., Bardel, P., Robertson, D. W., & Leander, J. D. Synthesis and anticonvulsant activities of alpha-heterocyclic alpha-acetamido-N-benzylacetamide derivatives. Journal of Medicinal Chemistry, 1993; 36(22), 3350-3360.
  • [12]. Kohn, H. L., Salomé, C., Park, K. D., & Salomé-Grosjean, E. N-benzylamide substituted derivatives of 2-(acylamido)acetic acid and 2-(acylamido)propionic acids: potent neurological agents. U.S. Patent and Trademark Office, Washington, DC; 2015; U.S. Patent No. 8,933,065 . [13]. King, A. M., Yang, X. F., Wang, Y. Y., Dustrude, E. T., Barbosa, C., Due, M. R., Piekarz, A. D., Wilson, S. M., White, F. A., Salome, C., Cummins, T. R., Khanna, R., Kohn, H., Identification of the Benzyloxyphenyl Pharmacophore: A Structural Unit That Promotes Sodium Channel Slow Inactivation. ACS Chemical Neuroscience 2012; 3 (12), 1037-1049.
  • [14]. Park, K. D., Yang, X. F., Dustrude, E. T., Wang, Y., Ripsch, M. S., White, F. A., & Kohn, H. Chimeric Agents Derived from the Functionalized Amino Acid, Lacosamide, and the α-Aminoamide, Safinamide: Evaluation of Their Inhibitory Actions on Voltage-Gated Sodium Channels, and Antiseizure and Antinociception Activities and Comparison with Lacosamide and Safinamide. ACS Chemical Neuroscience, 2014; 6(2), 316-330.
  • [15]. Hoppe, D., Beckmann, L. Selective Monoalkylation and Dialkylatıon of N-[Bis(Alkylthio)Methylene]Glycine Ethyl-Ester for Synthesis of Higher and Alpha-Branched Alpha-Amino-Acids. Liebigs Annalen der Chemie 1979; Issue: 12, p2066-2075.
There are 14 citations in total.

Details

Subjects Engineering
Journal Section Special
Authors

Mustafa Kemal Gümüş

Publication Date April 24, 2017
Published in Issue Year 2017 Volume: 38 Issue: 2

Cite

APA Gümüş, M. K. (2017). Synthesis and Identification of New Chiral Compounds Containing Azomethine Ylide Core. Cumhuriyet Üniversitesi Fen Edebiyat Fakültesi Fen Bilimleri Dergisi, 38(2), 264-274. https://doi.org/10.17776/cumuscij.297283
AMA Gümüş MK. Synthesis and Identification of New Chiral Compounds Containing Azomethine Ylide Core. Cumhuriyet Üniversitesi Fen Edebiyat Fakültesi Fen Bilimleri Dergisi. April 2017;38(2):264-274. doi:10.17776/cumuscij.297283
Chicago Gümüş, Mustafa Kemal. “Synthesis and Identification of New Chiral Compounds Containing Azomethine Ylide Core”. Cumhuriyet Üniversitesi Fen Edebiyat Fakültesi Fen Bilimleri Dergisi 38, no. 2 (April 2017): 264-74. https://doi.org/10.17776/cumuscij.297283.
EndNote Gümüş MK (April 1, 2017) Synthesis and Identification of New Chiral Compounds Containing Azomethine Ylide Core. Cumhuriyet Üniversitesi Fen Edebiyat Fakültesi Fen Bilimleri Dergisi 38 2 264–274.
IEEE M. K. Gümüş, “Synthesis and Identification of New Chiral Compounds Containing Azomethine Ylide Core”, Cumhuriyet Üniversitesi Fen Edebiyat Fakültesi Fen Bilimleri Dergisi, vol. 38, no. 2, pp. 264–274, 2017, doi: 10.17776/cumuscij.297283.
ISNAD Gümüş, Mustafa Kemal. “Synthesis and Identification of New Chiral Compounds Containing Azomethine Ylide Core”. Cumhuriyet Üniversitesi Fen Edebiyat Fakültesi Fen Bilimleri Dergisi 38/2 (April 2017), 264-274. https://doi.org/10.17776/cumuscij.297283.
JAMA Gümüş MK. Synthesis and Identification of New Chiral Compounds Containing Azomethine Ylide Core. Cumhuriyet Üniversitesi Fen Edebiyat Fakültesi Fen Bilimleri Dergisi. 2017;38:264–274.
MLA Gümüş, Mustafa Kemal. “Synthesis and Identification of New Chiral Compounds Containing Azomethine Ylide Core”. Cumhuriyet Üniversitesi Fen Edebiyat Fakültesi Fen Bilimleri Dergisi, vol. 38, no. 2, 2017, pp. 264-7, doi:10.17776/cumuscij.297283.
Vancouver Gümüş MK. Synthesis and Identification of New Chiral Compounds Containing Azomethine Ylide Core. Cumhuriyet Üniversitesi Fen Edebiyat Fakültesi Fen Bilimleri Dergisi. 2017;38(2):264-7.

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https://doi.org/10.1007/s10593-018-2247-5
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