一种新型1,3,4-噁二嗪酮化合物的合成及其晶体结构

引用本文: 孙宏顺, 王建强, 谭文文, 杨海东, 李玉龙, 沈临江, 郭成. 一种新型1,3,4-噁二嗪酮化合物的合成及其晶体结构[J]. 有机化学, 2016, 36(3): 622-625. doi: 10.6023/cjoc201509033 shu

Citation: Sun Hongshun, Wang Jianqiang, Tan Wenwen, Yang Haidong, Li Yulong, Shen Linjiang, Guo Cheng. Synthesis and Crystal Structure of a Novel 1,3,4-Oxadiazin-one Compound[J]. Chinese Journal of Organic Chemistry, 2016, 36(3): 622-625. doi: 10.6023/cjoc201509033 shu

一种新型1,3,4-噁二嗪酮化合物的合成及其晶体结构

孙宏顺 ^a,b, ,
王建强 ^a, ,
谭文文 ^b, ,
杨海东 ^b, ,
李玉龙 ^b, ,
沈临江 ^{a,
,} ,
郭成 ^a,

1.
a 南京工业大学化学与分子工程学院南京 211816;
2.
b 南京科技职业学院化学工程系南京 210048

通讯作者: 沈临江

基金项目:
国家自然科学青年基金(No. 21106069) (No. 21106069)

南京科技职业学院院级重点(No. NHKY-2015-1)资助项目. (No. NHKY-2015-1)

摘要: 以苯并噻吩-2-甲酸为原料, 经酯化、肼解、肼的酰基化和环化四步反应合成了一种新型化合物2-(2-苯并噻吩基)-4H-1,3,4-噁二嗪-5(6H)-酮(4). 产物结构经¹H NMR, ¹³C NMR, ESI-MS, FT-IR, 元素分析及X单晶衍射表征.

关键词:

苯并噻吩
/ 噁二嗪
/ 合成
/ 晶体结构

English

Synthesis and Crystal Structure of a Novel 1,3,4-Oxadiazin-one Compound

1.
a College of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816;
2.
b Department of Chemical Engineering, Nanjing Polytechnic Institute, Nanjing 210048

Corresponding author: 沈临江

Received Date: 25 September 2015
Available Online: 06 November 2015
Fund Project:
国家自然科学青年基金(No. 21106069)

南京科技职业学院院级重点(No. NHKY-2015-1)资助项目.

Abstract: Using benzothiophene-2-carboxylic acid as a raw material, 2-(1-benzothiophen-2-yl)-4H-1,3,4-oxadiazin-5(6H)-one (4) was synthesized by esterification and hydrazinolysis, followed by the acylation and cyclization reactions. The novel compound 4 was characterized by ¹H NMR, ¹³C NMR, ESI-MS, FT-IR, elemental analysis and X-ray single crystal diffraction.

Key words:

1. [1] Sieardi, S. M.; Landam, S.; Gaozza, C. H. J. Heterocycl. Chem. 1973, 10, 1039.[1] Sieardi, S. M.; Landam, S.; Gaozza, C. H. J. Heterocycl. Chem. 1973, 10, 1039.
2. [2] Li, Y.-X. Hunan Chem. Ind. 1995, 25, 12 (in Chinese). (李玉新, 湖南化工, 1995, 25, 12.)[2] Li, Y.-X. Hunan Chem. Ind. 1995, 25, 12 (in Chinese). (李玉新, 湖南化工, 1995, 25, 12.)
3. [3] Stephen, F. M.; Gary, D.; Annis, R. S.; David, W. P. Pest Manage. Sci. 2001, 57, 153.[3] Stephen, F. M.; Gary, D.; Annis, R. S.; David, W. P. Pest Manage. Sci. 2001, 57, 153.
4. [4] Cao, S.; Qian, X.-H.; Song, G.-H. J. Fluorine Chem. 2002, 117, 63.[4] Cao, S.; Qian, X.-H.; Song, G.-H. J. Fluorine Chem. 2002, 117, 63.
5. [5] Liu, C.-L. Pesticides 2004, 24, 42 (in Chinese). (刘长令, 农药, 2004, 24, 42.)[5] Liu, C.-L. Pesticides 2004, 24, 42 (in Chinese). (刘长令, 农药, 2004, 24, 42.)
6. [6] Gaonkar, S. L.; Rai, K. M. L.; Prabhuswamy, B. Eur. J. Med. Chem. 2006, 41, 841.[6] Gaonkar, S. L.; Rai, K. M. L.; Prabhuswamy, B. Eur. J. Med. Chem. 2006, 41, 841.
7. [7] Jeffrey, L. R.; Scott, W. M.; Nicholas, A. M. J. Med. Chem. 2007, 50, 528.[7] Jeffrey, L. R.; Scott, W. M.; Nicholas, A. M. J. Med. Chem. 2007, 50, 528.
8. [8] Ke, S.-Y.; Qian, X.-H.; Li, Z. Eur. J. Med. Chem. 2009, 44, 2113.[8] Ke, S.-Y.; Qian, X.-H.; Li, Z. Eur. J. Med. Chem. 2009, 44, 2113.
9. [9] Dong, M.; Cao, J.; Chen, L.; Lü, D.-H.; Hu, J.; Shen, Z.; Ni, C.-C.; Zhang, Y.-B.; Yuan, L.-P. Agrochemicals 2009, 48, 726 (in Chinese). (董敏, 曹瑾, 陈亮, 吕冬华, 胡军, 沈宙, 倪长春, 张一宾, 袁莉萍, 农药, 2009, 48, 726.)[9] Dong, M.; Cao, J.; Chen, L.; Lü, D.-H.; Hu, J.; Shen, Z.; Ni, C.-C.; Zhang, Y.-B.; Yuan, L.-P. Agrochemicals 2009, 48, 726 (in Chinese). (董敏, 曹瑾, 陈亮, 吕冬华, 胡军, 沈宙, 倪长春, 张一宾, 袁莉萍, 农药, 2009, 48, 726.)
10. [10] Sun, L.; Cao, J.; Chen, L.; Lü, D.-H.; Ni, C.-C.; Shen, Z.; Yuan, L.-P.; Zhang, Y.-B. Chin. J. Pestic. Sci. 2010, 12, 221 (in Chinese). (孙亮, 曹瑾, 陈亮, 吕冬华, 倪长春, 沈宙, 袁莉萍, 张一宾, 农药学学报, 2010, 12, 221.)[10] Sun, L.; Cao, J.; Chen, L.; Lü, D.-H.; Ni, C.-C.; Shen, Z.; Yuan, L.-P.; Zhang, Y.-B. Chin. J. Pestic. Sci. 2010, 12, 221 (in Chinese). (孙亮, 曹瑾, 陈亮, 吕冬华, 倪长春, 沈宙, 袁莉萍, 张一宾, 农药学学报, 2010, 12, 221.)
11. [11] Pan, L.-L.; Shen, X.-X.; Cao, J.; Chen, L.; Shen, Z.; Yuan, L.-P.; Zhang, Y.-B. Chin. J. Pestic. Sci. 2011, 13, 239 (in Chinese). (潘玲玲, 沈晓霞, 曹瑾, 陈亮, 沈宙, 袁莉萍, 张一宾, 农药学学报, 2011, 13, 239.)[11] Pan, L.-L.; Shen, X.-X.; Cao, J.; Chen, L.; Shen, Z.; Yuan, L.-P.; Zhang, Y.-B. Chin. J. Pestic. Sci. 2011, 13, 239 (in Chinese). (潘玲玲, 沈晓霞, 曹瑾, 陈亮, 沈宙, 袁莉萍, 张一宾, 农药学学报, 2011, 13, 239.)
12. [12] Walter, H. WO 0034286, 2000 [Chem. Abstr. 2000, 133, 30738d].[12] Walter, H. WO 0034286, 2000 [Chem. Abstr. 2000, 133, 30738d].
13. [13] Demirayak, S.; Mohsen, U. A. Heterocycl. Chem. 2001, 38, 507.[13] Demirayak, S.; Mohsen, U. A. Heterocycl. Chem. 2001, 38, 507.
14. [14] Jennings, L. D.; Kincaid, S. L.; Wang, Y. D.; Krishnamurthy, G.; Beyer, C. F.; McGinnis, J. P.; Miranda, M.; Discafani, C. M.; Rabindran, S. K. Bioorg. Med. Chem. Lett. 2005, 15, 4731.[14] Jennings, L. D.; Kincaid, S. L.; Wang, Y. D.; Krishnamurthy, G.; Beyer, C. F.; McGinnis, J. P.; Miranda, M.; Discafani, C. M.; Rabindran, S. K. Bioorg. Med. Chem. Lett. 2005, 15, 4731.
15. [15] Wang, H.-M.; Guo, S.-B.; Hu, Z.-G.; Zeng, X.-H.; Yang, G.-Y. Chin. J. Org. Chem. 2015, 35, 1075 (in Chinese). (王红梅, 郭树兵, 胡扬根, 曾小华, 杨光义, 有机化学, 2015, 35, 1075.)[15] Wang, H.-M.; Guo, S.-B.; Hu, Z.-G.; Zeng, X.-H.; Yang, G.-Y. Chin. J. Org. Chem. 2015, 35, 1075 (in Chinese). (王红梅, 郭树兵, 胡扬根, 曾小华, 杨光义, 有机化学, 2015, 35, 1075.)
16. [16] Wu, Q.; Wu, Q.; Zhang, X.; Yang, J.-C.; Liu, C.-L. Agrochemicals 2010, 49, 5 (in Chinese). (吴峤, 伍强, 张茜, 杨吉春, 刘长令, 农药, 2010, 49, 5.)[16] Wu, Q.; Wu, Q.; Zhang, X.; Yang, J.-C.; Liu, C.-L. Agrochemicals 2010, 49, 5 (in Chinese). (吴峤, 伍强, 张茜, 杨吉春, 刘长令, 农药, 2010, 49, 5.)
17. [17] Tietze, L. F.; Lohmann, J. K.; Stadler, C. Synlett 2004, 1113.[17] Tietze, L. F.; Lohmann, J. K.; Stadler, C. Synlett 2004, 1113.
18. [18] Leonczak, P.; Gao, L.-J.; Ramadori, A. T.; Lescrinier, E.; Rozenski, J.; Jonghe, S. D.; Herdewijn, P. ChemMedChem 2014, 9, 2587.[18] Leonczak, P.; Gao, L.-J.; Ramadori, A. T.; Lescrinier, E.; Rozenski, J.; Jonghe, S. D.; Herdewijn, P. ChemMedChem 2014, 9, 2587.
19. [19] Shiota, T.; Yamagami, S.; Kataoka, K.; Endo, N.; Barnum, D.; Greene, J.; Moree, W.; Weinhouse, M. R.; Tarby, C. M. US 6686353, 2004 [Chem. Abstr. 2004, 140, 163894].[19] Shiota, T.; Yamagami, S.; Kataoka, K.; Endo, N.; Barnum, D.; Greene, J.; Moree, W.; Weinhouse, M. R.; Tarby, C. M. US 6686353, 2004 [Chem. Abstr. 2004, 140, 163894].
20. [20] Alphen, J. V. Recl. Trav. Chim. Pays-Bas 1929, 48, 417.[20] Alphen, J. V. Recl. Trav. Chim. Pays-Bas 1929, 48, 417.
21. [21] Ahn, S. H.; Jang, S. S.; Kim, Y. K.; Lee, K. J. Bull. Korean Chem. Soc. 2012, 33, 233.[21] Ahn, S. H.; Jang, S. S.; Kim, Y. K.; Lee, K. J. Bull. Korean Chem. Soc. 2012, 33, 233.
22. [22] Weissgerber; Kruber Chem. Ber. 1920, 53, 1564.[22] Weissgerber; Kruber Chem. Ber. 1920, 53, 1564.

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通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

一种新型1,3,4-噁二嗪酮化合物的合成及其晶体结构

通讯作者: 沈临江

English

Synthesis and Crystal Structure of a Novel 1,3,4-Oxadiazin-one Compound

Corresponding author: 沈临江

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通讯作者: 陈斌, bchen63@163.com

中国化学会秘书处

一种新型1,3,4-噁二嗪酮化合物的合成及其晶体结构

通讯作者: 沈临江

English

Synthesis and Crystal Structure of a Novel 1,3,4-Oxadiazin-one Compound

Corresponding author: 沈临江

CCS Chemistry：嵌段共聚物自组装成 “三明治”二维有机材料，实现纳米级压力传感功能

CCS Chemistry：颜徐州、鲍哲南： 你的皮肤可能是一片SPMs

CCS Chemistry：工作高效不疲劳，只须让催化剂动起来

CCS Chemistry：静电组装导向聚合- 聚电解质纳米凝胶量化制备新策略

CCS Chemistry：金黄色葡萄球菌醛基脱氢酶是如何识别特异性底物的？

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