Synthesis and Structures of 3-Aryl-6-methyl-1,6-dihydro- 1,2,4,5-tetrazines and Their Derivatives

Chin. J. Org. Chem. ›› 2010, Vol. 30 ›› Issue (02): 260-265. Previous Articles Next Articles

Full Papers

3-芳基-6-甲基-1,6-二氢-1,2,4,5-四嗪及其衍生物的合成和晶体结构

徐峰*^{,1，杨珍珍¹，胡惟孝²，奚立民¹}

(¹台州职业技术学院生物与化学工程系台州 318000)
(²浙江工业大学药学院杭州 310032)

收稿日期:2009-04-29 修回日期:2009-07-07 发布日期:2010-02-20
通讯作者: 徐峰 E-mail:xufeng901@126.com
基金资助:
国家级.国家自然科学基金

Synthesis and Structures of 3-Aryl-6-methyl-1,6-dihydro- 1,2,4,5-tetrazines and Their Derivatives

Xu Feng*^{,1 Yang Zhenzhen¹ Hu Weixiao² Xi Limin¹}

(¹Department of Biological & Chemical Engineering, Taizhou Vocational & Technical College, Taizhou 318000)
(²College of Pharmaceutical Science, Zhejiang University of Technol-ogy, Hangzhou 310032)

Received:2009-04-29 Revised:2009-07-07 Published:2010-02-20
Contact: Feng Xu E-mail:xufeng901@126.com

Abstract

A convenient and effective method was developed from the starting materials acetonitrile and aryl nitrile via three steps to synthesize 3-aryl-6-methyl-1,6-dihydro-1,2,4,5-tetrazines. On the basis of which, some 3-aryl-6-methyl-1,6-dihydro-1,2,4,5-tetrazine derivatives were synthesized and characterized by elemental analysis, ¹H NMR, IR and HRMS techniques. The X-ray single crystal diffraction study of 6-methyl-3-phenyl-N-(2-tolyl)-1,6-dihydro-1,2,4,5-tetrazine-1-carboxamide (5a) indicates that 5a belongs to a monoclinic system, with a＝1.3941(6) nm, b＝0.5675(2) nm, c＝2.0614(8) nm; α＝γ＝90°, β＝102.055(6)°; V＝1.5949(11) nm³. The central tetrazine ring adopts an unsymmetrical boat structure. It could be considered that the molecule had a homoaromaticity.

Key words: 1,6-dihydro-1,2,4,5-tetrazine, unsymmetry, crystal structure, homoaromaticity

Cite this article

XU Feng, YANG Zhen-Zhen, HU Wei-Xiao, XI Li-Min. Synthesis and Structures of 3-Aryl-6-methyl-1,6-dihydro- 1,2,4,5-tetrazines and Their Derivatives[J]. Chin. J. Org. Chem., 2010, 30(02): 260-265.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Qifan Wang, Yuanquan Zhang, Li Xing, Yuanxiang Zhou, Chenyu Gong, Bangcan He, Nian Zhang, Yongjun Wu, Wei Xue. Design, Synthesis and Biological Activity of Myricetin Derivatives Containing 1,2,4-Triazolo[3,4-b]-1,3,4-thiadiazole [J]. Chinese Journal of Organic Chemistry, 2023, 43(4): 1525-1536.
[2]	Jing Wang, Linlin Wu, Qian Wang. Synthesis and Characterization of New Indeno[1,2-b]fluorene-6,12-dione Derivatives [J]. Chinese Journal of Organic Chemistry, 2023, 43(1): 223-228.
[3]	Chensheng Yu, Han Wang, Lijing Min, Liang Han, Jianjun Shi, Xinghai Liu. Synthesis, Cyrstal Structure and Fungicidal Activity of New Triazole Compounds Containing Trifluoromethylphenyl Moiety [J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4498-4503.
[4]	He Mei, He Chaofan, Liu Ling, Ye Jiao, Hu Aixi, Chen Yun, Xu Lujie, Liu Ailin. Synthesis, Crystal Structure and Neuraminidase Inhibitory Activity of 1,2,4-Triazole-3-sulfide Derivatives [J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2402-2410.
[5]	Jia Huijie, Han Limin, Zhu Ning, Gao Yuanyuan, Wang Yaqi, Suo Quanling. A Study on Recognition Property of Acetylferrocenyl Benzothiazole to Al³⁺, Cr³⁺ and Fe³⁺ [J]. Chin. J. Org. Chem., 2019, 39(6): 1753-1760.
[6]	Zhao Bangtun, Fu Huimin, Chen Xiaoji, Zhu Weimin. A New Method for Synthesizing Tetrathiafulvalene Vinylogues [J]. Chin. J. Org. Chem., 2018, 38(8): 2116-2121.
[7]	Shi Juan, Zhang Zunting. Synthesis and Fluorescent Property of Benzo [c]coumarin Carboxylic Derivatives [J]. Chin. J. Org. Chem., 2018, 38(6): 1462-1468.
[8]	Zhang Weijie, Xu Li, Song Jinsheng, Ma Zhiying, Wang Hua. Synthesis of Saddle-Shaped Cyclooctatetrathiophene-Triazine Derivatives and Their Aggregation Induced Emissions (AIE) Properties [J]. Chin. J. Org. Chem., 2018, 38(5): 1119-1125.
[9]	Mroz Robert, Vezzu Dileep A. K., Wallace Brian, Ravindranathan Deepak, Carroll Jeffrey, Pike Robert D., Huo Shouquan. A Comparative Study on Phosphorescent Cycloplatinated Complexes Based on Tridentate C^N^N-Coordinating Ligands and Phenylethynyl or Phenyl Ligand [J]. Chin. J. Org. Chem., 2018, 38(1): 171-182.
[10]	Zhang Meimei, Wang Jie, Liu Jianquan, Wang Xiangshan. One-Pot and Three-Component Synthesis of Furopyridoquinoxaline Derivatives under Catalyst-Free Conditions [J]. Chin. J. Org. Chem., 2017, 37(6): 1565-1570.
[11]	Chen Sufang, Hong Yubiao, Liu Yuanzhong, Xue Mingqiang, Zheng Yu, Shen Qi. Synthesis and Properties of Sodium and Europium(Ⅲ) Cryptates Incorporating the 4,4'-Substituted-2,2'-bipyridine Units [J]. Chin. J. Org. Chem., 2017, 37(5): 1198-1204.
[12]	Zhang Wenlong, Chen Dongmei, Liu Xingli, Huang Chao, Zhu Bixue. Synthesis, Structure and Anion Recognition of Urea-Functionalized Schiff Base Macrocyclic Compound [J]. Chin. J. Org. Chem., 2017, 37(2): 474-479.
[13]	Ou Yaping, Zhang Jing, Yu Jiangxi, Zhu Xiaoming. Synthesis, Spectral Properties and Theoretical Studies of 1,4-Bis[2-(4-pyridyl)ethenyl]benzene Derivatives [J]. Chin. J. Org. Chem., 2017, 37(2): 394-402.
[14]	Ren Yaping, Liu Xu, Wang Rui, Zhou Yuanqing, Li Biao, Xu Yan, Song Maoping. Synthesis and Properties of 4-Ferrocenyl-benzoyl-thiadiazole Derivatives [J]. Chin. J. Org. Chem., 2017, 37(1): 110-115.
[15]	Kang Haixia, Bai Jing, Xi Zhentao, Zhang Manman, Fu Yuqin, Zou Dapeng. Reaction of 5(R)-(l-Menthoxy)-2(5H)-furanone with Diethyl Bromomalonate [J]. Chin. J. Org. Chem., 2016, 36(8): 1915-1920.

3-芳基-6-甲基-1,6-二氢-1,2,4,5-四嗪及其衍生物的合成和晶体结构

Synthesis and Structures of 3-Aryl-6-methyl-1,6-dihydro- 1,2,4,5-tetrazines and Their Derivatives

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments