Hydroxymethylation and Aminomethylation of 2-Aminothiazol Derivatives at 5 Position

doi:10.6023/cjoc1106152

Chin. J. Org. Chem. ›› 2012, Vol. ›› Issue (03): 601-607.DOI: 10.6023/cjoc1106152 Previous Articles Next Articles

Notes

2-氨基噻唑5 位的羟甲基化和胺甲基化

王锋^a, 李稳宏^a, 李冬^a, 范峥^a, 李珍^b

a 西北大学化工学院西安 710069;
b 陕西省石油化工研究设计院西安 710054

收稿日期:2011-06-15 修回日期:2011-10-20 发布日期:2012-03-24
通讯作者: 李稳宏 E-mail:liwenhong@nwu.edu.cn

Hydroxymethylation and Aminomethylation of 2-Aminothiazol Derivatives at 5 Position

Wang Feng^a, Li Wenhong^a, Li Dong^a, Fan Zheng^a, Li Zhen^b

a School of Chemical Engineering, Northwest University, Xi'an 710069;
b Shaanxi Research Design Institute of Petroleum and Chemical Industry, Xi'an 710054

Received:2011-06-15 Revised:2011-10-20 Published:2012-03-24

Hydroxymethylation of 2-aminothiazol derivatives at 5 position irritated by microwave was reported. The reaction results were compared by the method of microwave, sealed tube and reduction from ester. A series of novel hydroxymethyl derivatives were obtained. Through the experiments, sealed tube condition demanded high thermal stability of the substrate, and the reaction yield was low with messy reaction solution and long reaction time. The yield of reduction from ester is poor with longer synthetic route. The hydroxymethylation under microwave irradiation gave high yields with short reaction times. 2-Cyanoacetate sodium salt was prepared from NaH, and the yield was improved. Novel derivatives of aminomethylation on 5 position are obtained after cyclization and reduction.

Key words: 2-aminothiazole, microwave reaction, thiazole

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Wang Feng, Li Wenhong, Li Dong, Fan Zheng, Li Zhen. Hydroxymethylation and Aminomethylation of 2-Aminothiazol Derivatives at 5 Position[J]. Chin. J. Org. Chem., 2012, (03): 601-607.

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[1] Kearney, P. C.; Fernandez, N.; Flygare, J. A. J. Org. Chem. 1998,63(1), 196.

[2] Haviv, F.; Ratajczyk, J. D.; DeNet, R. W.; Kerdesky, F. A.; Walters,R. L.; Schmidt, S. P.; Holms, J. H.; Young, P. R.; Carter, G.W. J. Med. Chem. 1988, 31(9), 1719.

[3] Clemence, F.; Marter, O. L.; Delevalle, F.; Benzoni, J.; Jouanen,A.; Jouquey, S.; Mouren, M.; Deraedt, R. J. Med. Chem. 1988,31(7), 1453.

[4] Palmer, P. J.; Trigg, R. B.; Warrington, J. V. J. Med. Chem. 1971,14(3), 248.

[5] Wagner, B.; Schumann, D.; Linne, U.; Koert, U.; Marahiel, M. A.J. Am. Chem. Soc. 2006, 128(32), 10513.

[6] Liu, H.; Li, Z.; Anthonsen, T. Molecules 2000, 5(9), 1055.

[7] Xia, Z. P.; Smith, C. D. J. Org. Chem. 2001, 66(10), 3459.

[8] Zav'yalov, S. I.; Dorofeeva, O. V.; Rumyantseva, E. E.; Kulikova,L. B.; Ezhova, G. I.; Kravchenko, N. E.; Zavozin, A. G. Pharm.Chem. J. 2001, 35(2), 96.

[9] Jimonet, P.; Audiau, F.; Barreau, M.; Blanchard, J. C.; Boireau, A.;Bour, Y.; Coleno, M. A.; Doble, A.; Doerflinger, G.; Huu, C. D.;Donat, M. H.; Duchesne, J. M.; Ganil, P.; Gueremy, C.; Honore, E.;Just, B.; Kerphirique, R.; Gontier, S.; Hubert, P.; Laduron, P. M.;Blevec, J. L.; Meunier, M.; Miquet, J. M.; Nemecek, C.; Pasquet,M.; Piot, O.; Pratt, J.; Rataud, J.; Reibaud, M.; Stutzmann, J. M.;Mignani, S. J. Med. Chem. 1999, 42(15), 2828.

[10] Rae, D. R.; Gibson, S. G. EP 368384, 1990 [Chem. Abstr. 1990,113, 191335].

[11] Sandra, T.; Denise, A. C.; Patrick, D. S.; Michael, P. H.; William,A. D.; Amato, J. G. Cancer Cell 2008, 14, 90.

[12] Turcotte, S.; Chan, D. A.; Sutphin, P. D.; Giaccia, A. J.; Hay, M.P.; Denny, W. A.; Bonney, M. M. WO 2009114552, 2009 [Chem.Abstr. 2009, 151, 381337].

[13] Dales, N.; Fonarev, J.; Fu, J. M.; Kamboj, R.; Kodumuru, V.; Liu,S. F.; Pokrovskaia, N. ; Raina, V.; Sun, S. Y.; Zhang, Z. H.; WO2008127349, 2008 [Chem. Abstr. 2008, 149, 493672].

[14] Siddiqui, H. L.; Zia-Ur-Rehman, M.; Ahmad, N.; Weaver, G. W.;Lucas, P. D. Chem. Pharm. Bull. 2007, 55(7), 1014.

[15] Chaudhari, S. S.; Thomas, A. P. N. P.; Deshmukh, V. G.;Khairatkar, J. N.; Mukhopadhyay I. WO 2009144548, 2009 [Chem.Abstr. 2009, 152, 12030].

[16] Ghiron, C.; Nencini, A.; Micco, I.; Zanaletti, R.; Maccari, L.;Bothmann, H.; Haydar, S.; Varrone, M.; Pratelli, C.; Harrison, B.WO 2008087529, 2008 [Chem. Abstr. 2008, 149, 20092].

[17] Liu, W.; Xiao, H.; Yang, Y. Q.; Zhao, G.; Zhou, J.; Zheng, C. W.;Chen, X. K.; Guo, Y. L. Tetrahedron 2011, 67, 1768.

[18] Goodyer, C. L. M.; Chinje, E. C.; Jaffar, M.; Stratford, I. J.;Threadgill, M. D. Bioorg. Med. Chem. 2003, 11(19), 4189.

[19] Siddiqui, H. L.; Zia-Ur-Rehman, M.; Ahmad, N.; Weaver, G. W.;Lucas, P. D. Chem. Pharm. Bull. 2007, 55, 1014.

[20] Bayer, C. A.; Goergens, U.; Mihara, J.; Murata, T.; Yamazaki, D.;Yoneta, Y.; Araki, K.; Sasaki, N.; Domon, K.; Hatazawa, M.; Shimojo,E.; Icihara, T.; Ataka, M.; Shibuya, K. WO 2010043315,2010 [Chem. Abstr. 2010, 152, 453944].

[21] Chuaqui, C.; Cossrow, J.; Dowling, J.; Guan, B.; Hoemann, M.;Ishchenko, A.; Jones, J. H.; Kabigting, L.; Kumaravel, G.; Peng,H.; Powell, N.; Raimundo, B.; Tanaka, H.; Van, V. K.; Vessels, J.;Xin, Z. L. WO 2010078408, 2010 [Chem. Abstr. 2010, 153,174965].

[22] Michael, P. H.; Sandra, T.; Jack, U. F.; Muriel. B.; Denise, A. C.;Patrick, D. S.; Phuong N.; Amato, J. G.; William, A. D. J. Med.Chem. 2010, 53(2), 787.

[23] Al-Qalaf, F.; Abdelkhalik, M. M.; Bassam, A. A.; Mandani, F.Molecules 2009, 14(1), 78.

[24] Kihara, M.; Kashimoto, M.; Kobayashi, Y.; Nagao, Y. Heterocycles1992, 34(4), 747.

[25] Tillu, V. H.; Shinde, P. D.; Bedekar, A. V.; Wakharkar, R. D. Synth. Commun. 2003, 33(8), 1399.

[26] Sakata, M.; Shirakawa, Y.; Kamata, N.; Sakaguchi, Y.; Nishino, H.;Ouyang, J.; Kurosawa, K. J. Heterocycl. Chem. 2000, 37(2), 269.

[27] Ahluwalia, V. K.; Arora, K. K.; Kaur, G.; Mehta, B. Synth. Commun.1987, 17(3), 333.

[28] Prakash, R.; Kumar, A.; Aggarwal, R.; Prakash, O.; Singh, S. P.Synth. Commun. 2007, 37(15), 2501.

[29] Saeed, B.; Sahar, N.; Shokat, H. Synth. Commun. 2008, 38, 2521.

2-氨基噻唑5 位的羟甲基化和胺甲基化

Hydroxymethylation and Aminomethylation of 2-Aminothiazol Derivatives at 5 Position

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