跳至主要内容

Simple Reduction of Hydantoins with Sodium Borohydride

Read full paper at:
http://www.scirp.org/journal/PaperInformation.aspx?PaperID=52659#.VKCoXcCAM4

The reduction of various hydantoins with sodium borohydride gave the corresponding 4-hydroxy- 2-imidazolidinones in high yields. In contrast, reduction employing a boron trifluoride etherate-sodium borohydride system generated 2-imidazolidinones. In both reductions, the reactivity of the hydantoin was dependent on its substituents. The Lewis acid-promoted reactions of a 4-hydroxy-2-imidazolidinone with nucleophiles were also investigated.
Cite this paper
Yamaguchi, J. , Shibuta, E. and Oishi, Y. (2014) Simple Reduction of Hydantoins with Sodium Borohydride. International Journal of Organic Chemistry, 4, 286-291. doi: 10.4236/ijoc.2014.45031.
 

[1] Yamaguchi, J., Harada, M., Narushima, T., Saitoh, A., Nozaki, K., and Suyama, T. (2005) Diastereoselective Conjugate Addition of 1-(a,b-Unsaturated acyl)hydantoin with Nucleophiles. Tetrahedron Letters, 46, 6411-6415.
http://dx.doi.org/10.1016/j.tetlet.2005.07.116
[2] Chavan, S.P., Tejwani, R.B. and Ravindranathan, T. (2001) A Switch of Reactivity Profile in Ionic Intramolecular Annulation Reactions: A Short and Efficient Synthesis of D-(+)-Biotin. Journal of the Organic Chemistry, 66, 6197-6201.
http://dx.doi.org/10.1021/jo015730j
[3] Chavan, S.P., Chittiboyina, A.G., Ravindranathan, T., Kamat, S.K. and Kalkote, U.R. (2005) Diastereoselective Amidoalky- lation of (3S,7aR)-6-Benzyl-7-hydroxy-3-phenyltetrahydro-5H-imiazo[1,5-c][1,3]thiazol-5-one: A Short and Highly Efficient Synthesis of (+)-Biotin. Journal of the Organic Chemistry, 70, 1901-1903.
http://dx.doi.org/10.1021/jo0488107
[4] Wilk, I.J. and Close, W.J. (1950) The Action of Lithium Aluminum Hydride on 3-Methyl-5-phenylhydantoin and 5- Phenylhydantoin. Journal of the Organic Chemistry, 15, 1020-1022.
http://dx.doi.org/10.1021/jo01151a017
[5] Li, C.-D., Lee, M.H. and Sartorelli, A.C. (1979) Synthesis and Biological Evaluation of Tetramisole Analogues as Inhibitors of Alkaline Phosphatase of the 6-Thiopurine-Resistant Tumor Sarcoma 180/TG1. Journal of Medicinal Chemistry, 22, 1030-1033.
http://dx.doi.org/10.1021/jm00195a003
[6] Marshall, F.J. (1956) Lithium Aluminum Hydride Reduction of Some Hydantoins, Barbiturates and Thiouracils. The Journal of American Chemical Society, 78, 3696-3697.
http://dx.doi.org/10.1021/ja01596a038
[7] Cortes, S. and Kohn, H. (1983) Selective Reductions of 3-Substituted Hydantoins to 4-Hydroxy-2-imidazolidinones and Vicinal Diamines. Journal of the Organic Chemistry, 48, 2246-2254.
http://dx.doi.org/10.1021/jo00161a021
[8] Cortes, S. and Kohn, H. (1983) Selective Reductions of 3-Substituted Hydantoins to 4-Hydroxy-2-imidazolidinones and Vicinal Diamines. Journal of the Organic Chemistry, 48, 2246-2254.
http://dx.doi.org/10.1021/jo00161a021
[9] Liao, Z.-K. and Kohn, H. (1984) Synthesis of Substituted 2-Imidazolidinones and Annelated Hydantoin via Amidoalkylation Transformations. Journal of the Organic Chemistry, 49, 4745-4752.
http://dx.doi.org/10.1021/jo00199a001
[10] Moolenaar, M.J., Speckamp, W.N., Hiemstra, H., Poetsch, E. and Casutt, M. (1995) Synthesis of D-(+)-Biotin through Selective Ring Closure of N-Acyliminium Silyl Enol Ether. Angewandte Chemie International Edition, 34, 2391-2393.
http://dx.doi.org/10.1002/anie.199523911
[11] Drewes, S.E., Malissar, D.G.S. and Roos, G.H.P. (1993) Ephedrine-Derived Imidazolidin-2-Ones. Broad Utility Chiral Auxiliaries in Asymmetric Synthesis. Chemische Berichte, 126, 2663-2673.
http://dx.doi.org/10.1002/cber.19931261216
[12] Taguchi, T., Shibuya, A., Sasaki, H., Endo, J., Morikawa, T. and Shiro, M. (1994) Asymmetric Synthesis of Difluorocyclopropanes. Tetrahedron: Asymmetry, 5, 1423-1426.
http://dx.doi.org/10.1016/0957-4166(94)80101-0
[13] Bongini, A., Cardillo, G., Gentilucci, L. and Tomasini, C. (1997) Synthesis of Enantiomerically Pure Aziridine-2-Imides by Cyclization of Chiral 3’-Benzyloxyamino Imide Enolates. Journal of Organic Chemistry, 62, 9148-9153.
http://dx.doi.org/10.1021/jo971254e
[14] Guillena, G. and Najera, C. (1998) PTC and Organic Bases-LiCl Assisted Alkylation of Imidazolidinone-Glycine Iminic Derivatives for the Asymmetric Synthesis of α-Amino Acids. Tetrahedron: Asymmetry, 9, 3935-3938.
http://dx.doi.org/10.1016/S0957-4166(98)00402-9
[15] Guillena, G. and Najera, C. (2000) 1,5-Dimethyl-4-Phenylimidazolidin-2-One-Derived Iminic Glycinimides: Useful New Reagents for Practical Asymmetric Synthesis of α-Amino Acids. Journal of Organic Chemistry, 65, 7310-7322.
http://dx.doi.org/10.1021/jo000321t
[16] Kim, T.H. and Lee, G.-J. (1999) Regiocontrolled Cyclization Reaction of N-(2-Hydroxy)Ureas by Transfer of Activation: One-Pot Synthesis of 2-Imidazolidinones. Journal of Organic Chemistry, 64, 2941-2943.
http://dx.doi.org/10.1021/jo9820061
[17] Kim, T.H. and Lee, G.-J. (2000) L-Valinol and L-Phenylalaninol-Derived 2-Imidazolidinones as Chiral Auxiliaries in Asymmetric Aldol Reactions. Tetrahedron Letters, 41, 1505-1508.
http://dx.doi.org/10.1016/S0040-4039(99)02325-4
[18] Nadir, U.K., Krishna, R.V. and Singh, A. (2005) A New and Facile Route for the Synthesis of Chiral 1,2-Diamines and 2,3-Diamino Acids. Tetrahedron Letters, 46, 479-482.
http://dx.doi.org/10.1016/j.tetlet.2004.11.088
[19] Tschantz, M.A., Burgess, L.E. and Meyers, A.I. (1996) (S)-(-)-5-Heptyl-2-pyrrolidineone. Chiral Bicyclic Lactams as Templates for Pyrrolidines and Pyrrolidinones. Organic Synthesis, 73, 221-230.        eww141229lx

评论

此博客中的热门博文

Does Immigration Promote the Investment of the Monopolistic Firm?

In the present paper, we examine the effect of increasing uncertainty of immigrants’ growth on the optimal timing of investment of a firm that has a monopolistic power over the labor market. It is revealed that when the uncertainty of immigrants’ growth is more than a threshold level, increasing uncertainty of immigrants’ growth accelerates the optimal timing of firms’ investment and enhances the economic growth, even if the uncertainty of immigrants’ growth is formulated by the geometric Brownian motion, which is in sharp contrast to the standard result that an increase in the uncertainty postpones the optimal timing. With an increase in the immigrants over the past ten years, workforces in the host countries have been growing significantly to the extent that the immigrants represent 70% of the increase in the workforce in Europe, and 47% in the United States as OECD indicates. In the present paper, we attempted to investigate the effect of increased uncertainty caused by the growi...

Education Policy Implementation: A Mechanism for Enhancing Primary Education Development in Zanzibar

Education is one of the fundamental rights of individuals; therefore, the government of a country needs to develop and strengthen educational policy and quality as well as to ensure that everyone has equal access to basic education. The improvement of access and quality of education in the world is becoming as an essential factor in development, whereas the basic education (primary school), is acknowledged as a foundation of the higher educational development for every country. To fulfill this goal, governments introduce several policies and procedures; however, it requires some reforms and participation from the politician, policymakers, and other stakeholders to re-examine educational policy so that it can lead to multiplication and betterment of the reforms. Educational reforms actually focus on accountability. A positive educational development and reform is very challenging and needs more effort and strategy on how to use and utilize the resources effectively as such it can achie...