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Journals / Cumhuriyet Üniversitesi Fen-Edebiyat Fakültesi Fen Bilimleri Dergisi / 2017 / Cilt: 38 - Sayı: 2

Synthesis and Identification of New Chiral Compounds Containing Azomethine Ylide Core

Azometin Yilür Çekirdeği İçeren Yeni Kiral Bileşiklerin Sentezi ve Yapılarının Aydınlatılması

Mustafa Kemal GÜMÜŞ
Pages
264–274
Publication Date
2022-10-11
DOI
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AI Summary & Key Takeaways

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

These compounds were characterized by different spectroscopic techniques (IR, H NMR, 13C NMR ve COSY NMR).

📌 3 Key Takeaways

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Objective & Hypothesis: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).
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Key Findings & Data:These compounds contain the azomethine ylide core, which is used as 1,3-dipole reactant in 1,3-dipolar cycloaddition reactions.
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Conclusion & Impact:These compounds were characterized by different spectroscopic techniques (IR, H NMR, 13C NMR ve COSY NMR).
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Domain Parameters

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, H NMR, 13C NMR ve COSY NMR).

Özet

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.

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Cite This Article

GÜMÜŞ, M. K. (2022). Synthesis and Identification of New Chiral Compounds Containing Azomethine Ylide Core. Cumhuriyet Üniversitesi Fen-Edebiyat Fakültesi Fen Bilimleri Dergisi, Cilt: 38 - Sayı: 2, 264–274. https://ajindex.com/articles/480359

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References (1)

  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 ag