SIOC English
有机化学
高级检索

有机化学 >

2022 , Vol. 42 >Issue 6: 1778 - 1785

DOI: https://doi.org/10.6023/cjoc202111031

研究论文

无金属条件下酰胺和酯参与的2-取代苯并噁唑衍生物的合成

  • 李芳绍 ,
  • 肖晶 ,
  • 吴小芳 ,
  • 王晓熠 ,
  • 邓金凤 ,
  • 唐子龙
展开
  • 湖南科技大学化学化工学院 理论有机化学与功能分子教育部重点实验室 湖南湘潭 411201

收稿日期: 2021-11-22

  修回日期: 2022-02-08

  网络出版日期: 2022-02-25

基金资助

国家自然科学基金(21703061); 湖南省科技创新计划(2021RC5028)

收起

Metal-Free Formation of 2-Substitued Benzoxazoles with Amides and Esters

  • Fangshao Li ,
  • Jing Xiao ,
  • Xiaofang Wu ,
  • Xiaoyi Wang ,
  • Jinfeng Deng ,
  • Zilong Tang
Expand
  • Key Laboratory of Theoretical Organic Chemistry and Functional Molecule of Ministry of Education, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, Hunan 411201
*E-mail: ;

Received date: 2021-11-22

  Revised date: 2022-02-08

  Online published: 2022-02-25

Supported by

National Natural Science Foundation of China(21703061); Science and Technology Innovation Program of Hunan Province(2021RC5028)

Fold

摘要

2-取代苯并噁唑是一类重要的杂环骨架, 因其特有的生理活性在医药中有广泛应用. 以三氯化磷和碘为促进剂, 一锅法实现多种惰性酰胺和酯对苯并噁唑衍生物的C(2)位官能团化, 为无金属条件下一系列2-取代苯并噁唑衍生物的合成提供了简单高效的新方法. 同时考察了不同酰胺和酯类化合物的反应活性, 结果表明在该体系下酰胺的反应活性高于酯的反应活性. 该方法具有条件简单、成本低廉以及良好的底物范围等优点, 并提出了可能的反应机理.

关键词： 2-取代苯并噁唑; 酰胺; 酯; 无金属; 三氯化磷

本文引用格式

李芳绍 , 肖晶 , 吴小芳 , 王晓熠 , 邓金凤 , 唐子龙 . 无金属条件下酰胺和酯参与的2-取代苯并噁唑衍生物的合成[J]. 有机化学, 2022 , 42(6) : 1778 -1785 . DOI: 10.6023/cjoc202111031

Abstract

2-Substituted benzoxazoles are important heterocyclic motifs due to their wide application in pharmacology. A PCl3-mediated C(2)-functionalization of benzoxazole derivatives with inert amides and esters under metal-free conditions was reported. By using PCl3/I2 combination, various 2-substituted benzoxazoles could be synthesized via the arylation or alkylation of benzoxazoles with amides and esters in the presence of water. What’s more, the reactivity between amides and esters was also investigated. The primary results indicated that amides have higher reactivity than esters under this system. This method features a broad substrate scope, simple condition and low-cost. A plausible mechanism was also proposed.

Key words： 2-substituted benzoxazoles; amide; ester; metal-free; phosphorus trichloride

参考文献

[1]
Dondoni, A. In Comprehensive Heterocyclic Chemistry II, Vol. 3, Ed.: Shinkai, I. E., Pergamon, Glasgow, 1996, p. 373.
[2]
Noe?l, S.; Cadet, S.; Gras, E.; Hureau, C. Chem. Soc. Rev. 2013, 42, 7747.
[3]
Zhang, Y.; Li, W.; Wang, Q.; Zhang, R.; Xiong, Q.; Shen, X.; Guo, J.; Chen, X. Acta Chim. Sinica 2013, 71, 1496. (in Chinese)
[3]
( 张勇, 李伟, 王强, 张若璇, 熊启杰, 沈祥, 郭靖, 陈雪梅, 化学学报, 2013, 71, 1496.)
[4]
Ram, V. J.; Sethi, S.; Nath, M.; Pratap, R. In The Chemistry of Heterocycles Nomenclature and Chemistry of Three-to-Five Membered Heterocycles, Elsevier, Amsterdam, 2019, pp. 149-478.
[5]
Zhang, W.; Zeng, Q. I.; Zhang, X. M.; Tian, Y. J.; Yue, Y.; Guo, Y. J.; Wang, Z. H. J. Org. Chem. 2011, 76, 4741.
[6]
Gao, F.; Kim, B.-S.; Walsh, P. J. Chem. Commun. 2014, 50, 10661.
[7]
(a) Wang, B.; Zhang, Y.; Li, P.; Wang, L. Chin. J. Chem. 2010, 28, 1697.
[7]
(b) Fan, X.; He, Y.; Wang, Y.; Zhang, X.; Wang, J. Chin. J. Chem. 2011, 29, 773.
[7]
(c) Xiao, L.; Gao, H.; Kong, J.; Liu, G. Chin. J. Org. Chem. 2014, 34, 1048. (in Chinese)
[7]
( 肖立伟, 高红杰, 孔洁, 刘光仙, 彭晓霞, 王树军, 有机化学, 2014, 34, 1048.)
[8]
Wei, Y.; Hu, P.; Zhang, M.; Su, W. Chem. Rev. 2017, 117, 8864.
[9]
Perry, G. J. P.; Larrosa, I. Eur. J. Org. Chem. 2017, 2017, 3517.
[10]
Rouchet, B. E. Y.; Hachem, M.; Schneider, C.; Hoarau, C. ACS Catal. 2017, 7, 5363.
[11]
Li, Y.; Qian, F.; Wang, M.; Lu, H.; Li, G. Org. Lett. 2017, 19, 5589.
[12]
Choy, P. Y.; Wong, S. M.; Kapdi, A.; Kwong, F. Y. Org. Chem. Front. 2018, 5, 288.
[13]
Teo, Y. C.; Riduan, S. N.; Zhang, Y. Green Chem. 2013, 15, 2365.
[14]
Wang, L.; Ren, X.; Yu, J.; Jiang, Y.; Cheng, J. J. Org. Chem. 2013, 78, 12076.
[15]
Wu, A.; Chen, Q.; Liu, W.; You, L.; Fu, Y.; Zhang, H. Org. Chem. Front. 2018, 5, 1811.
[16]
Yang, Z.; Zhou, L.; Liu, Y.; Lu, H.; Wu, F.; Xie, Y.; Liu, J. ChemistrySelect 2019, 4, 13788.
[17]
Niu, Z.-J.; Li, L.-H.; Liu, X.-Y.; Liang, Y.-M. Adv. Synth. Catal. 2019, 361, 5217.
[18]
Rao, M. S.; Hussain, S. Synth. Commun. 2021, 51, 2684.
[19]
(a) Li, F.; Wu, X.; Guo, F.; Tang, Z.-L.; Xiao, J. Eur. J. Org. Chem. 2021, 4314.
[19]
(b) Wu, X.; Zhou, L.; Yang, R.; Guo, F. Tang, Z.-L.; Xiao, J. J. Chem. Res. 2020, 44, 301.
[19]
(c) Xiao, J.; Han, L.-B. J. Chem. Res. 2019, 43, 205.
[20]
Xiao, J.; Guo, F.; Li, Y.; Li, F.; Li, Q.; Tang, Z.-L. J. Org. Chem. 2021, 86, 2028.
[21]
Lv, F.; Xiao, J.; Xiang, J.; Guo, F.; Tang, Z.-L.; Han, L.-B. J. Org. Chem. 2021, 86, 3081.
[22]
Wang, Y.; Yu, X.; Fu, H.; Zheng, X.; Chen, H.; Li, R. Chin. J. Org. Chem. 2019, 39, 1482. (in Chinese)
[22]
( 汪洋点点, 余晓军, 付海燕, 郑学丽, 陈华, 李瑞祥, 有机化学, 2019, 39, 1482.)
[23]
Jadhav, J.; Gaikwad, V.; Kurane, R.; Salunkhe, R.; Rashinkar, G. Tetrahedron 2013, 69, 2920.
[24]
Teimouri, A.; Chermahini, A. N.; Salavati, H.; Ghorbanian, L. J. Mol. Catal. A-Chem. 2013, 373, 38.
[25]
Jiang, Y. CN 101667623A, 2006.
[26]
Putta, R.; Chun, S.; Choi, S. H.; Lee, S. B.; Oh, D.; Hong, S. J. Org. Chem. 2020, 85, 15396.
[27]
Datta, A. Orient. J. Chem. 2021, 37, 341.
[28]
Saha, P.; Ramana, T.; Purkait, N.; Ali, M. A.; Paul, R.; Punniyamurthy, T. J. Org. Chem. 2009, 74, 8719.
[29]
Wang, Y.; Sarris, K.; Sauer, D. R.; Djuric, S. W. Tetrahedron Lett. 2006, 47, 4823.
[30]
Kebede, E.; Tadikonda, R.; Nakka, M.; Inkollu, B.; Vidavalur, S. Eur. J. Org. Chem. 2015, 27, 5929.
[31]
Evindar, G.; Batey, R. A. J. Org. Chem. 2006, 71, 1802.
[32]
Dr, Y. N.; Kashihara, N.; Kanyiva, K. S.; Prof, T. H. Angew. Chem., nt. Ed. 2010, 49, 4451.
[33]
Jacky, C. Y.; Masakazu, N.; Cathleen, M. C. Org. Lett. 2017, 19, 3715.
[34]
Nguyen, L. A.; Dang, T. D.; Ngo, Q. A.; Nguyen, T. B. Eur. J. Org. Chem. 2020, 25, 3818.
[35]
Babu, K. R.; Zhu, N.; Bao, H. Org. Lett. 2017, 19, 46.
Options
文章导航

/

〈 〉