1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)-Promoted Stere-oselective Synthesis of Oxazolidin-2-(thi)one Derivatives

doi:10.6023/cjoc201704036

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (12): 3177-3185.DOI: 10.6023/cjoc201704036 Previous Articles Next Articles

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1,8-二氮杂二环十一碳-7-烯(DBU)立体选择性催化合成噁唑啉-2-(硫)酮衍生物

杨权力^a, 宋玉叶^a, 余平^a, 王龙^b, 刘明国^a, 黄年玉^a

a 三峡大学生物与制药学院天然产物研究与利用湖北省重点实验室宜昌 443002;
b 三峡大学材料与化工学院宜昌 443002

收稿日期:2017-04-21 修回日期:2017-08-10 发布日期:2017-09-08
通讯作者: 黄年玉 E-mail:hny115@126.com
基金资助:
国家自然科学基金（No.21602123）及三峡大学青年拔尖人才项目和研究生创新基金（No.SDYC2016121）资助项目.

1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)-Promoted Stere-oselective Synthesis of Oxazolidin-2-(thi)one Derivatives

Yang Quanli^a, Song Yuye^a, Yu Ping^a, Wang Long^b, Liu Mingguo^a, Huang Nianyu^a

a Hubei Key Laboratory of Natural Products Research and Development, College of Biological and Pharmaceutical Sciences, China Three Gorges University, Yichang 443002;
b College of Materials and Chemical Engineering, China Three Gorges University, Yichang 443002

Received:2017-04-21 Revised:2017-08-10 Published:2017-09-08
Contact: 10.6023/cjoc201704036 E-mail:hny115@126.com
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21602123), the Youth Talent Development Foundation and Scientific Foundation from Graduate School of China Three Gorges University (No. SDYC2016121).

1. 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)-Promoted Stere-oselective Synthesis of Oxazolidin-2-(thi)one Derivatives.PDF(11894KB)

Abstract

A series of multi-substituted oxazolidin-2-(thi)one derivatives were prepared via 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) promoted nucleophilic addition/cyclization from alkynyl alcohol and isocynate or thiocynate in high yields of 75%~95%. This concise and efficient approach provides a facial access to a library of biological (Z)-arylmethylene substituted oxazolidin-2-(thi)one derivatives with high stereo-selectivities.

Key words: oxazolidin-2-(thi)one, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), stereo-selectivity

Cite this article

Yang Quanli, Song Yuye, Yu Ping, Wang Long, Liu Mingguo, Huang Nianyu. 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)-Promoted Stere-oselective Synthesis of Oxazolidin-2-(thi)one Derivatives[J]. Chin. J. Org. Chem., 2017, 37(12): 3177-3185.

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[1] Zappia, G.; Menendez, P.; Monache, G. D.; Misiti, D.; Nevola, L.; Botta, B. Mini-Rev. Med. Chem. 2007, 7, 389.
[2] (a) Phillips, O. A.; Sharaf, L. H. Expert Opin. Ther. Pat. 2016, 26, 591.
(b) Jadhavar, P. S.; Vaja, M. D.; Dhameliya, T. M.; Chakraborti, A. K. Curr. Med. Chem. 2015, 22, 4379.
[3] (a) Fujita, T.; Yamago, S. Chem.-Eur. J. 2015, 21, 18547.
(b) Green, R.; Peed, J.; Taylor, J. E.; Blackburn, R. A.; Bull, S. D. Nat. Protoc. 2013, 8, 1890.
[4] Ferreira, J.; Rees-Jones, S. C.; Ramaotsoa, V.; Msutu, A.; Hunter, R. Org. Biomol. Chem. 2016, 14, 1545.
[5] (a) Guo, B.; Fan, H.; Xin, Q.; Chu, W.; Wang, H.; Huang, Y.; Chen, X.; Yang, Y. J. Med. Chem. 2013, 56, 2642.
(b) Friggeri, L.; Ballante, F.; Ragno, R.; Musmuca, I.; De Vita, D.; Manetti, F.; Biava, M.; Scipione, L.; Di Santo, R.; Costi, R.; Feroci, M.; Tortorella, S. J. Chem. Inf. Model. 2013, 53, 1463.
[6] (a) Njiojob, C. N.; Bozell, J. J.; Long, B. K.; Elder, T.; Key, R. E.; Hartwig, W. T. Chem.-Eur. J. 2016, 22, 12506.
(b) Mydock-McGrane, L.; Rath, N. P.; Covey, D. F. J. Org. Chem. 2014, 79, 5636.
[7] Mendes, R. E.; Deshpande, L. M.; Jones, R. N. Drug Resist. Updates 2014, 17, 1.
[8] Chahine, E. B.; Sucher, A. J.; Knutsen, S. D. Consult. Pharm. 2015, 30, 386.
[9] (a) Xu, J. X.; Zhao, J. W.; Jia, Z. B. Chin. Chem. Lett. 2011, 22, 1063.
(b) Li, Y. W.; Liu, Y.; Jia, Y. C.; Yuan, J. Y. Chin. Chem. Lett. 2013, 24, 230.
[10] (a) Sadeghzadeh, S. M. Appl. Organomet. Chem. 2016, 30, 835.
(b) Bacchi, A.; Chiusoli, G. P.; Costa, M.; Gabriele, B.; Righi, C.; Salerno, G. Chem. Commun. 1997, 1209.
(c) Song, Q. W.; Zhou, Z. H.; Wang, M. Y.; Zhang, K.; Liu, P.; Xun, J. Y.; He, L. N. ChemSusChem 2016, 9, 2054.
(d) Hu, J.; Ma, J.; Zhu, Q.; Zhang, Z.; Wu, C.; Han, B. Angew. Chem., Int. Ed. 2015, 54, 5399.
(e) Hase, S.; Kayaki, Y.; Ikariya, T. ACS Catal. 2015, 5, 5135.
[11] (a) Fujisaki, F.; Abe, N.; Sumoto, K. Heterocycles 2008, 75, 1681.
(b) Steiner, B.; Langer, V.; Koóš, M. Carbohydr. Res. 2009, 344, 2079.
[12] (a) Li, S. Q.; Xiong, P.; Zhu, L.; Qian, X. Y.; Xu, H. C. Eur. J. Org. Chem. 2016, 2016, 3449.
(b) Sekine, K.; Mawatari, T.; Yamada, T. Synlett 2015, 26, 2447.
(c) Kim, W. S.; Yoon, E.; Jo, K. A.; Kang, E. J. Bull. Korean Chem. Soc. 2011, 32, 3158.
[13] (a) Lu, X. F.; Yang, Z.; Huang, N. Y.; He, H. B.; Deng, W. Q.; Zou, K. Bioorg. Med. Chem. Lett. 2015, 25, 3726.
(b) Wang, L.; Xie, Y. B.; Huang, N. Y.; Yan, J. Y.; Hu, W. M.; Liu, M. G.; Ding, M. W. ACS Catal. 2016, 6, 4010.
(c) Li, R. K.; Yang, Q. L.; Liu, Y.; Li, D. W.; Huang, N. Y.; Liu, M. G. Chin. Chem. Lett. 2016, 27, 345.
[14] Li, S.; Ye, J.; Yuan, W.; Ma, S. Tetrahedron 2013, 69, 10450.
[15] Zhao, J.; Huang, H.; Qi, C.; Jiang, H. Eur. J. Org. Chem. 2012, 29, 5665.
[16] (a) Ritter, S.; Horino, Y.; Lex, J.; Schmalz, H. G. Synlett 2006, 3309.
(b) Ramesh, R.; Chandrasekaran, Y.; Megha, R.; Chandrasekaran, S. Tetrahedron 2007, 63, 9153.
(c) Hu, M.; Song, R. J.; Li, J. H. Angew. Chem., Int. Ed. 2015, 54, 608.
[17] (a) Doherty, S.; Knight, J. G.; Perry, D. O.; Ward, N. A.; Bittner, D. M.; McFarlane, W.; Probert, M. R. Organometallics 2016, 35, 1265.
(b) Wang, F.; Wang, Y.; Cai, L.; Miao, Z.; Chen, R. Adv. Synth. Catal. 2008, 350, 2733.
(c) Hu, Y.; Xin, X.; Wan, B. Tetrahedron Lett. 2014, 55, 32.
[18] (a) Hashmi, A.; Stephen K.; Wang, T.; Shi, S.; Rudolph, M. J. Org. Chem. 2012, 77, 7761.
(b) Engel, D. A.; Dudley, G. B. Org. Lett. 2006, 8, 4027.
(c) Jagtap, S. R.; Bhanage, B. M. J. Chem. Res. 2007, 6, 370.
(d) Smissman, E. E.; Johnsen, R. H.; Carlson, A. W.; Aycock, B. F. J. Org. Chem. 1956, 78, 3395.
(e) Cooper, M. A.; Lucas, M. A.; Taylor, J. M.; Ward, A. D.; Williamson, N. M. Synthesis 2001, 621.
(f) Moran, W. J.; Rodríguez, A. Org. Biomol. Chem. 2012, 10, 8590.
(g) Zhang, H.; Tanimoto, H.; Morimoto, T.; Nishiyama, Y.; Kakiuchi, K. Org. Lett. 2013, 20, 5222.

1,8-二氮杂二环十一碳-7-烯(DBU)立体选择性催化合成噁唑啉-2-(硫)酮衍生物

1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)-Promoted Stere-oselective Synthesis of Oxazolidin-2-(thi)one Derivatives

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