The Synthesis of Some Aromatics Aminoalcohols and Characterization of Their Structures

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.

Keywords

• Epoxide, aminolysis, β-aminoalcohols, β-blockers

Bazı Aromatik Aminoalkollerin Sentezi ve Yapılarının Aydınlatılması

Abstract

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.

Keywords

• Epoksit, aminoliz, β-aminoalkoller, β-blokerler

References

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)
10. 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)
11. Grayson M., Ed.. Kirk-Othmer Encyclopedia of Chemical Technology 17, 311 (1982)
12. 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 Nisopropylphenoxypropanolamines. Eur. J. Med. Chem. 34, 919-937 (1999)
13. Kordık CH.P., Reıtz A.B. Pharmacological Treatment of Obesity : Therapeutic strategies. J.Med. Chem. 42,182-205 (1999)
14. Brode O.E., Kroemer H.K. Drug-drug Interactions of β –Adrenoceptor Blockers. Arzneim.-Forsch./ Drug Res., 53, 814-822 (2003)
15. Toda F., Tanaka K. Conversion of Rasemic Cyanohydrin into One Optically Active Isomer in the Presence of Brucina. Chem. Lett., 661 (1983)
16. Račanská E., Švec P. Use of Beta-Blockers in Current Therapy and the Prospect of Their Further Development . Farm. Obz., 76, 63-66 (1997)
17. Čıžmárıková R. β -Adrenergic Receptor Blockers- the Group of Chiral Drugs: Different Effect of Individual Enantiomers. Čes. Slov. Farm. .51, 121-128 (2002)
18. Steiner, D.D. Optically Pure Amino Alcohols Derived from Commercially Available Limonene Oxide: Efficient Ligants for Asymmetric Alkylation of Carbonyls. PhD Thesis, Universty of California, Santa Cruz (2003).