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Journals / Selçuk Üniversitesi Fen Fakültesi Fen Dergisi / 2010 / Cilt: 2 - Sayı: 35

The Synthesis of Some Aromatics Aminoalcohols and Characterization of Their Structures

Bazı Aromatik Aminoalkollerin Sentezi ve Yapılarının Aydınlatılması

Arzu UYANIK
Nejdet ŞEN
Sultan KURBANLI
Yakup KAR
Pages
33–42
Publication Date
2010-12-01
DOI
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AI Summary & Key Takeaways

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

The synthesized compounds were characterized by the spectroscopic methods such as elemental analyses, 1H NMR and IR.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:In this study, the aromatic aminoalcohols 2, 3, 4 and 5, which are of special interest in the field of drugs; and also widely used in asymmetric synthesis, were synthesized from the nucleophilic ring opening reactions of 1-phenoxy-2,3-epoxypropane (1) with ammonia, isopropylamine, piperidine and morpholine.
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Key Findings & Data:The compound 1 used as starting material, was synthesized from the reaction of epichlorohydrine with phenol.
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Conclusion & Impact:The synthesized compounds were characterized by the spectroscopic methods such as elemental analyses, 1H NMR and IR.
🔬Design:Research Article
📍Scope:Comprehensive Sample
⚙️Variables:Epoksit · aminoliz · β-aminoalkoller

Abstract

In this study, the aromatic aminoalcohols 2, 3, 4 and 5, which are of special interest in the field of drugs; and also widely used in asymmetric synthesis, were synthesized from the nucleophilic ring opening reactions of 1-phenoxy-2,3-epoxypropane (1) with ammonia, isopropylamine, piperidine and morpholine. The compound 1 used as starting material, was synthesized from the reaction of epichlorohydrine with phenol. The synthesized compounds were characterized by the spectroscopic methods such as elemental analyses, 1H NMR and IR.

Özet

Bu çalışmada, 1-fenoksi-2,3-epoksipropanın (1) amonyak, izopropilamin, piperidin ve morfolin ile nükleofilik halka açılma reaksiyonundan ilaç sanayinde özel bir ilgiye sahip olan ve asimetrik sentezlerde yaygın olarak kullanılan 2, 3, 4, 5 numaralı β-aminoalkoller sentezlenmiştir. Fenol ile epiklorhidrinin reaksiyonundan ise çıkış maddesi olarak kullanılan 1 numaralı bileşik sentezlenmiştir. Sentezlenen bileşiklerin yapıları elementel analiz, 1H NMR ve IR gibi spektroskopik yöntemlerle aydınlatılmıştır.

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Cite This Article

UYANIK, A., ŞEN, N., KURBANLI, S., KAR, Y. (2010). The Synthesis of Some Aromatics Aminoalcohols and Characterization of Their Structures. Selçuk Üniversitesi Fen Fakültesi Fen Dergisi, Cilt: 2 - Sayı: 35, 33–42. https://ajindex.com/articles/800418

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References (11)

  1. Huerta G., Contreras-Ordoñez G., Alvarez-Toledano C., Santes V., Gómez E., and Toscano R.A. Facile Synthesis of Aminoalcohols by Ring Opening of Epoxides Under Solvent Free Conditions. Synthetic Communications, 34 (13), 2393-2406 (2004)
  2. Anger, D.J., Prakash, I., Schaad, D.R. 1,2- Amino Alcohols and Their Heterocyclic Derivatives as Chiral Auxiliaries in Asymmetric Synthesis. Chem. Rev., 96 (2), 835-875 (1996)
  3. Iida, T., Yamamoto, N., Sasai, H., Shibasaki, M. New Asymmetric Reactions Using a Gallium Complex: a Highly Enantioselective Ring Opening of Epoxides with Thiols Catalyzed by a Gallium-lithium-bis(binapthoxide) Complex. J. Am. Chem. Soc., 119 (20), 4783-4784 (1997)
  4. Wu, M.H., Jacobsen, E.N.J. Asymmetric Ring Opening of Meso Epoxides with Thiols: Enantiomeric Enrichment Using a Bifonctional Nucleophile. Org. Chem. 63 (15), 5252-5254 (1998)
  5. Buono, G. On the Beneficial Effect of Ortho-methoxy Groups in the Asymmetric Ring Opening of Meso Epoxides with Silicon Tetrachloride Catalyzed by Chiral Orthomethoxyphenyldiazaphosphonamide Lewis Bases. Angew. Chem. Int. Ed. 40 (24), 4536 (2001)
  6. Adams, H., Bell, R., Cheung, Y.-Y., Jones, D.N., Tomkinson, N.C.O. The Cleavege of Meso-epoxides with Homochiral Thiols: Synthesis of (+)- and (-)- trans-1-mercaptocyclohexan-ol. Tetrahedron: Asymmetry. 10 (21), 4129-4149 (1999)
  7. Wu, J., Hou, X.-L., Dai. L.-X., Xia, L.-J., Tang, M.-H. Enantioselective Ring Opening of Mesoepoxides with Thiols Catalyzed by a Chiral (salen) Ti(IV) Complex. Tetrahedraon: Asymmetry. 9 (19), 3431-3436 (1998)
  8. Rogers, G.A., Parsons, Andersons, D.C., Nilsson, L.M., Bahr, B.A., Kornreich, W.D., Kaufman, R., Jacobs, R.S., Kirtman, B. Synthesis, in Vitro Acetylcholine-Storage-Blocking Activities, and Biological Properties of Derivatives and Analogues of Trans-2-(4phenylpeperidino)cyclohexanol (vesamicol). J.Med. Chem. 32 (6), 1217-1230 (1989)
  9. Kurbanlı, S., Şen, N., Güler, E and Koçak, A. The Investigation of the Alkylation Reactions of Hydroxy and En-Oximes with Some Halohydrins and Epoxides 34 (9), 1663-1675 (2004) Harris C.E. A Novel Synthesis of Aminoalcohols and the Chromium (VI) and Supported Permanganate Oxidation Aminoalcohols, Enamines, and Oximes. PhD Thesis, Universty of California, Santa Cruz (1997)
  10. Grayson M., Ed. Kirk-Othmer Encyclopedia of Chemical Technology 17, 311 (1982)
  11. Louıs S.N., Nero T.L., Iakovıdıs D., Colagrande F.M., Jackman G.P., Louıs W.J. β1- and β2Adrenoreceptor Antagonist Activity of a Series of Parasubstitued Nisopropylphen