Solvent-Free Synthesis of Novel Chiral Aromatic Amide Molecular Tweezers under Microwave Irradiation

Chin. J. Org. Chem. ›› 2009, Vol. 29 ›› Issue (10): 1621-1625. Previous Articles Next Articles

Full Papers

新的手性芳酰胺分子钳的微波干法合成

曾碧涛^a 赵志刚^*,b 赵潇湘^b 叶英^b 陈宇^b 石治川^b吴秀明^b

(^a宜宾职业技术学院宜宾 644003) (^b西南民族大学化学与环境保护工程学院成都 610041)

收稿日期:2009-05-24 修回日期:2009-07-10 发布日期:2009-09-20

Solvent-Free Synthesis of Novel Chiral Aromatic Amide Molecular Tweezers under Microwave Irradiation

Zeng, Bitao^a Zhao, Zhigang^*,b Zhao, Xiaoxiang^b Ye, Ying^b Chen, Yu^b Shi, Zhichuan^b Wu, Xiuming^b

(^a Yibin Vocational and Technical College, Yibin 644003) (^b College of Chemistry and Environmental Protection Engineering, Southwest University for Nationalities, Chengdu 610041)

Received:2009-05-24 Revised:2009-07-10 Published:2009-09-20

Abstract

Nine novel molecular tweezer artificial receptors have been designed and synthesized by using 1,3-phenylenedioxy acetic acid as spacer and L-amino acid methyl esters as arm in the solvent-free condi-tions under microwave irradiation. Their structures were confirmed by 1H NMR, IR, MS technique and ele-mental analysis. Compared with the conventional heating method, this method is simple, safe, rapid, effi-cient and eco-friendly. The preliminary results indicate that these chiral molecular tweezers have good enan-tioselective recognition for D/L- amino acid methyl esters.

Key words: 1,3-phenylenedioxy acetic acid, molecular tweezer, microwave irradiation, molecular recognition

Cite this article

CENG Bi-Chao, DIAO Zhi-Gang, DIAO Xiao-Xiang, XIE Yang. Solvent-Free Synthesis of Novel Chiral Aromatic Amide Molecular Tweezers under Microwave Irradiation[J]. Chin. J. Org. Chem., 2009, 29(10): 1621-1625.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Huang Guobao, Chen Zhilin, Wei Xiansheng, Chen Yu, Li Xiuying, Zhong Hui, Tan Mingxiong. Recent Progress on the Construction and Function of Macrocyclic Compounds Containing Hydrogen Bond Donors [J]. Chinese Journal of Organic Chemistry, 2020, 40(3): 614-624.
[2]	Wang Jiao, Yao Hong, Zhou Qi, Kan Xiaotong, Fan Yanqing, Guan Xiaowen, Zhang Youming, Lin Qi, Wei Taibao. Molecule-Responsive Supramolecular Hydrogel Constructed from Pillar[5]arene Based on Host-Guest System [J]. Chinese Journal of Organic Chemistry, 2020, 40(1): 175-180.
[3]	Xie Tinghui, Jiang Xiaoying, Mi Zhisheng, Li Xue, Xu Xiaohe, Bai Renren, Shuai Qi, Xie Yuanyuan. Iron/O₂-Promoted C-H Bond Functionalization for the Exclusive Synthesis of 2-Quinoline Carboxaldehydes under Microwave Irradiation [J]. Chinese Journal of Organic Chemistry, 2019, 39(11): 3294-3298.
[4]	Li, Sicong, Ji, Shaocong, Zhao, Liang, Liao, Xiaoyu, Liu, Chuanfeng, Tang, Haodong, Shu, Zhengning, Yang, Peng, Pei, Yuehu. Syntheses and Property Evaluation of N-Salicylaldehyde Hydrazone Modified 11-Azaartemisinins and Their Derivatives [J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2860-2866.
[5]	Liu Chuan-Zhi, Wang Hui, Zhang Dan-Wei, Zhao Xin, Li Zhan-Ting. Study on Halogen Bonding of Organofluorine Compounds in China [J]. Chin. J. Org. Chem., 2019, 39(1): 28-37.
[6]	Zong Chaoyang, Gu Huiwen, Zhang Lijie, Jin Yudong, Sun Yaquan. Microwave-Accelerated Dimroth Rearrangement for the Synthesis of Pyrido [2, 3-d]pyrimidin-4-amine Derivatives [J]. Chin. J. Org. Chem., 2018, 38(5): 1165-1171.
[7]	Sun Guangjun, Nie Chengbin, Zhao Xin, Li Zhanting. Intramolecular C-H…O Hydrogen Bonding-Driven 1,2,3-Trazole Foldamers:Assessment of Intermolecular C-H…X^- (X=Cl, Br, I) and C-H…N Hydrogen Bonding [J]. Chin. J. Org. Chem., 2017, 37(7): 1757-1763.
[8]	Qu Renyu, Chen Nian, Liu Yuchao, Chen Qiong, Yang Guangfu. An Efficient Synthesis of Functionalized 6-Arylsubstituted Salicylates via Microwave Irradiation [J]. Chin. J. Org. Chem., 2017, 37(5): 1266-1272.
[9]	Xiao Liwei, Ren Ping, Jing Xuemin, Ren Lilei, Li Zheng, Dai Fucai. Application in Molecular Recognition of 1,2,3-Trizole Derivatives [J]. Chin. J. Org. Chem., 2017, 37(12): 3085-3095.
[10]	Li Wenting, Qu Wenjuan, Zhang Haili, Li Xiang, Lin Qi, Yao Hong, Zhang Youming, Wei Taibao. Development on Application of Phenazine Derivatives in Molecular Recognition and Self-assembly [J]. Chin. J. Org. Chem., 2017, 37(10): 2619-2639.
[11]	Huang Yaobing, Yang Tao, Liu Anfeng, Zhou Xincheng, Pan Hui. Microwave-Assisted Alcoholysis of Cellulose to Methyl Levulinate Catalyzed by SnCl₄/H₂SO₄ [J]. Chin. J. Org. Chem., 2016, 36(6): 1438-1443.
[12]	Zhang Bianxiang, Yang Lihua, Shi Ruixue, Kang Yongqiang. Synthesis of Heterocyclic Aromatic Sulfides under Microwave Irradiation [J]. Chin. J. Org. Chem., 2016, 36(2): 352-357.
[13]	Zhang Rui, Pan Jinhuan, Wu Qiongyou. Copper Mediated One-Pot Multi-Component Synthesis of 3-Substitued Isoquinolines [J]. Chin. J. Org. Chem., 2016, 36(12): 2906-2911.
[14]	Liu Guijun, Shi Hao. Progress in Chiral Recognition Based on Molecular Tweezers [J]. Chin. J. Org. Chem., 2016, 36(11): 2583-2601.
[15]	Zhu Jihua, Zheng Xudong, Guo Guozhe, Zhang Yuquan, Wu Bowan. Microwave-Assisted Synthesis of Asymmetrical 1,5-Disubstituted Carbonohydrazide and Crystal Structure [J]. Chin. J. Org. Chem., 2015, 35(9): 1975-1980.

新的手性芳酰胺分子钳的微波干法合成

Solvent-Free Synthesis of Novel Chiral Aromatic Amide Molecular Tweezers under Microwave Irradiation

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments