A Convenient Synthesis of 5-Fluoroalkyloxazoline

doi:10.6023/cjoc201301071

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (08): 1782-1790.DOI: 10.6023/cjoc201301071 Previous Articles Next Articles

Articles

一种有效合成5-氟烷基噁唑啉的方法

杨波^a, 方向^a, 杨雪艳^a, 吴范宏^b

a 华东理工大学化学与分子工程学院上海 200237;
b 上海应用技术学院化学与环境工程学院上海 201418

收稿日期:2013-01-27 修回日期:2013-03-20 发布日期:2013-04-08
通讯作者: 杨雪艳, 吴范宏 E-mail:yxy@ecust.edu.cn;wfh@ecust.edu.cn
基金资助:
国家自然科学基金(Nos. 20972050, 21172148)资助项目.

A Convenient Synthesis of 5-Fluoroalkyloxazoline

Yang Bo^a, Fang Xiang^a, Yang Xueyan^a, Wu Fanhong^b

a School of Chemistry and Molecular Enineering, School of Chemistry and Molecular Enineering, East China University of Science and Technology, Shanghai 200237;
b School of Chemical and Environmental Engineering, Shanghai Institute of Technology, Shanghai 201418

Received:2013-01-27 Revised:2013-03-20 Published:2013-04-08
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 20972050, 21172148).

An efficient and convenient protocol for the synthesis of 5-fluoroalkyl-2-oxazoline is described. The 1-allyl-3-arylurea was synthesized by the reaction of isocyanate with allyl amine in methylene chloride at room temperature. The reaction of 1-allyl-3-arylurea with fluoroalky iodide initiated by sodium dithionite in aqueous acetonitrile resulted in adducts that undergoes a cyclization in water or DMF to form 5-fluoroalkyloxazoline with moderate yields. It was also found that the products can be more efficiently formed via an AIBN-initiated, one-pot addition-cyclization sequence from 1-allyl-3-arylurea with fluoroalkyl iodide.

Key words: oxazoline, fluorinated alkyl, O-cyclization, free radical reaction

Cite this article

Yang Bo, Fang Xiang, Yang Xueyan, Wu Fanhong. A Convenient Synthesis of 5-Fluoroalkyloxazoline[J]. Chin. J. Org. Chem., 2013, 33(08): 1782-1790.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Fortin, J. S.; Lacroix, J.; Desjardins, M.; Patenaude, A.; Petitclerc, E. R.; C-Gaudreault, R. Bioorg. Med. Chem. 2007, 15, 4456.
[2] Liu, B.-N.; Liu, M.; Liu, D.-K.; Liu, W.; Qi, H.-F. Chin. J. Synth. Chem. 2011, 19, 734 (in Chinese).
(刘冰妮, 刘默, 刘登科, 刘巍, 祁浩飞, 合成化学, 2011, 19, 734.)
[3] Béchard, P.; Lacroix, J.; Poyet, P.; C-Gaudreault, R. Eur. J. Med. Chem. 2009, 29, 963.
[4] Zhang, C.-S.; Ye, Y. Chin. J. Org. Chem. 2012, 32, 1336 (in Chinese).
(张长水, 叶勇, 有机化学, 2012, 32, 1336.)
[5] Zhang, C.-Y.; Liu, D.-K.; Sun, C.-H.; Liu, M.; Liu, W. Chin. J. Synth. Chem. 2012, 20, 425 (in Chinese).
(张存彦, 刘登科, 孙长海, 刘默, 刘巍, 合成化学, 2012, 20, 425.)
[6] Takasu, A.; Kojima, H. J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 5953.
[7] Tessier, A.; Pytkowicz, J.; Brigaud, T. J. Fluorine Chem. 2012, 134, 122.
[8] Tsuda, Y.; Kuriyama, M.; Onomura, O. Chem. Eur. J. 2012, 18, 2481.
[9] Wang, C.-Y.; Shang, Z.-C.; Leng, T.-H.; Yu, Q.-S. Chin. J. Org. Chem. 2003, 23, 384 (in Chinese).
(王成云, 商志才, 冷桃花, 俞庆森, 有机化学, 2003, 23, 384.)
[10] Li, W.-Z.; Wang, B.; Yao, J.-H.; Xu, Z.-L. Chin. J. Org. Chem. 2004, 24, 1239 (in Chinese).
(李伟杰, 汪波, 姚骏骅, 许遵乐, 有机化学, 2004, 24, 1239.)
[11] Khanum, S. A.; Khanum, N. F.; Shashikanth, M. Bioorg. Med. Chem. Lett. 2008, 18, 4597.
[12] Coeffard, V.; Muller-Bunz, H.; Guiry, P. J. Org. Biomol. Chem. 2009, 7, 1723.
[13] Mawo, R. Y.; Johnson, D. M.; Wood, J. L.; Smoliakova, I. P. J. Organomet. Chem. 2008, 693, 34.
[14] Hu, J.-F. Chin. J. Spectrosc. Lab. 2011, 28, 52 (in Chinese).
(胡军福, 光谱实验室, 2011, 28, 52.)
[15] Zhou, Y.-L.; Shen, S.-W.; Liu, F.-M. Chin. J. Org. Chem. 2010, 30, 1342 (in Chinese).
(周英雷, 沈松伟, 刘方明, 有机化学, 2010, 30, 1342.)
[16] Morais, G. R.; Oliveira, R. S.; Falconer, R. A. Tetrahedron Lett. 2009, 50, 1642.
[17] Liu, L.; Zheng, Z.-B.; Qin, Z.-H.; Fu, B.; Yuan, H.-Z. Chin. J. Org. Chem. 2008, 28, 1841 (in Chinese).
(刘磊, 郑中博, 覃兆海, 傅滨, 袁会珠, 有机化学, 2008, 28, 1841.)
[18] Zhang, H.-Z.; Zhou, C.-H.; Geng, R.-X.; Ji, Q.-G. Chin. J. Org. Chem. 2011, 31, 1963 (in Chinese).
(张慧珍, 周成合, 耿蓉霞, 吉庆刚, 有机化学, 2011, 31, 1963.)
[19] Guru, M. M.; Ali, M. A.; Punniyamurthy, T. J. Org. Chem. 2011, 76, 5444.
[20] Ganboa, I.; Palomo, C. Bull. Soc. Chim. Fr. 1982, 2, 167.
[21] Masuda, N.; Swern; Hideyuki, F. Antimicrob. Agents Chemother. 1996, 40, 1201.
[22] Yang, X. Y.; Fang, X.; Ju, Z. H.; Hu, Y. N.; Wu, F. H. Synthesis 2011, 3627.
[23] Yang, X. Y.; Wang, Z.; Zhu, Y. P.; Fang, X.; Yang, X. J.; Wu, F. H.; Shen, Y. J. J. Fluorine Chem. 2007, 128, 1046.
[24] Sanna, M.; White, P. D.; Chan, W. C. Tetrahedron Lett. 2008, 49, 6160.

一种有效合成5-氟烷基噁唑啉的方法

A Convenient Synthesis of 5-Fluoroalkyloxazoline

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Lijun Xu, Zongjun Li, Fushe Han, Xiang Gao. N,N-Dimethylformamide-Promoted Synthesis of Fullerene-Fused Oxazoline Derivatives [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 242-250.
[2]	Haoran Liu, Junhao Yu, Tongyang Cao, Lin Qi, Lijing Wang. N-Iodosuccinimide-Promoted Cascade Oxoazidation of Alkenyl Oximes: Synthesis of Azido Isoxazolines [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4220-4226.
[3]	Changming Dong, Yi Xie, Guangxin Liang. A Feasible Route to Access the ABD Skeleton in Azadirachtin-Type Limonoids [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2857-2866.
[4]	Li Dai, Di Xu, Yifei Mao, Jiaqi Zhu, Mengjiao Yang. Structures and Synthetic Strategies of Chiral Oxazolinyl Ferrocene Derivatives [J]. Chinese Journal of Organic Chemistry, 2022, 42(8): 2364-2375.
[5]	Lizhi Zhang, Yongjian Liao, Ning Chen, Lei Huang, Min Zhou. Cyclization and Coupling Reactions Promoted by Potassium tert-Butoxide [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 1950-1959.
[6]	Xuerong Chen, Liang Qi, Jinpei Huang, Weiwei Zhu, Yifeng Zhou. Lewis Acid Promoted Intramolecular Nucleophilic Heterocyclization of Unsaturated Amides for the Synthesis of 2-Oxazolines and Their Applications in Imaging of Living Cells [J]. Chinese Journal of Organic Chemistry, 2022, 42(7): 2155-2163.
[7]	Hao Xu, Jie Zhang, Junze Zuo, Fengxiao Wang, Jian Lü, Xu Hun, Daoshan Yang. Recent Advances in Visible-Light-Catalyzed C—C Bonds and C—Heteroatom Bonds Formation Using Sulfonium Salts [J]. Chinese Journal of Organic Chemistry, 2022, 42(12): 4037-4059.
[8]	Xintuo Yang, Pinhong Chen, Guosheng Liu. Asymmetric Palladium-Catalyzed Aza-Wacker Reaction of Alkenes: Efficient Synthesis of Chiral 1,3-Oxazinan-2-ones [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3382-3389.
[9]	Yunshu Liu, Guodong Zhao, Wenju Wu, Yunze Wang, Yanchao Yu, Jun You, Bo Liu. Study on Asymmetric Conjugate Cyanation of 3,5-Dimethyl-N-α,β-unsaturated Acylpyrazole Catalyzed by Magnesium-Bisoxazoline Complex [J]. Chinese Journal of Organic Chemistry, 2022, 42(1): 208-217.
[10]	Tao Wang, Xiaosha Wang, Yawen Song, Jingjing Huo, Jingshuan Zhou, Qingwei Kang, Lantao Liu. Cu(OAc)₂-Mediated C—H Bond Dithiolation of Amide-Oxazolines with Aryl Thiols [J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1098-1107.
[11]	Liu Yingjie, Meng Jianping, Li Chen, Lin Liqing, Xu Ying. Progress in the Synthesis of Isoxazoline Derivatives by Cycloylation of Allyl Oxime [J]. Chinese Journal of Organic Chemistry, 2020, 40(9): 2742-2754.
[12]	Liu Xinming, Li Lu, Jin Licheng, Zhao Jincan, Hua Yuanzhao, Wang Mincan, Liu Lantao. Oxidative Halocyclization of N-Allylarylamides with KX/Oxone System: Green Synthesis of 5-Halomethyl-2-Oxazolines [J]. Chinese Journal of Organic Chemistry, 2020, 40(12): 4298-4304.
[13]	Zhong Liangkun, Jiang Tao, Zhang Fan, Fu Qing, Liu Xinghai, Xu Tianming, Ding Chengrong, Chen Jie, Yuan Jing, Tan Chengxia. Synthesis and Insecticidal Activity of 3-Arylisoxazoline-pyrazole-5-carboxamide Derivatives [J]. Chin. J. Org. Chem., 2019, 39(9): 2655-2662.
[14]	Li Minglong, Cao Xixian, You Jun, Yu Yanchao, Wu Wenju, Liu Bo. Asymmetric 1,3-Dipolar Cycloaddition Reaction of C,N-Diarylnitrone with N-α,β-Unsaturated Acyl Compounds Catalyzed by Chiral Bisoxazoline Metal Complex [J]. Chin. J. Org. Chem., 2019, 39(6): 1642-1649.
[15]	Li Yongkun, Liu Bei, Zhang Lijun, Zhu Jiahong, Wan Chunping, Mao Zewei. Synthesis and Cytotoxic Activity of New 3-Aryl-5-furanyl-4, 5-dihydroisoxazoline Derivatives [J]. Chin. J. Org. Chem., 2018, 38(4): 949-954.