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

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

  • Corresponding author: Shen Linjiang, 
  • Received Date: 25 September 2015
    Available Online: 27 October 2015

    Fund Project: 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)

  • 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.
  • 加载中
    1. [1]

      [1] Sieardi, S. M.; Landam, S.; Gaozza, C. H. J. Heterocycl. Chem. 1973, 10, 1039.

    2. [2]

      [2] Li, Y.-X. Hunan Chem. Ind. 1995, 25, 12 (in Chinese). (李玉新, 湖南化工, 1995, 25, 12.)

    3. [3]

      [3] Stephen, F. M.; Gary, D.; Annis, R. S.; David, W. P. Pest Manage. Sci. 2001, 57, 153.

    4. [4]

      [4] Cao, S.; Qian, X.-H.; Song, G.-H. J. Fluorine Chem. 2002, 117, 63.

    5. [5]

      [5] Liu, C.-L. Pesticides 2004, 24, 42 (in Chinese). (刘长令, 农药, 2004, 24, 42.)

    6. [6]

      [6] Gaonkar, S. L.; Rai, K. M. L.; Prabhuswamy, B. Eur. J. Med. Chem. 2006, 41, 841.

    7. [7]

      [7] Jeffrey, L. R.; Scott, W. M.; Nicholas, A. M. J. Med. Chem. 2007, 50, 528.

    8. [8]

      [8] Ke, S.-Y.; Qian, X.-H.; Li, Z. Eur. J. Med. Chem. 2009, 44, 2113.

    9. [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.)

    10. [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.)

    11. [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.)

    12. [12]

      [12] Walter, H. WO 0034286, 2000 [Chem. Abstr. 2000, 133, 30738d].

    13. [13]

      [13] Demirayak, S.; Mohsen, U. A. Heterocycl. Chem. 2001, 38, 507.

    14. [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.

    15. [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.)

    16. [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.)

    17. [17]

      [17] Tietze, L. F.; Lohmann, J. K.; Stadler, C. Synlett 2004, 1113.

    18. [18]

      [18] Leonczak, P.; Gao, L.-J.; Ramadori, A. T.; Lescrinier, E.; Rozenski, J.; Jonghe, S. D.; Herdewijn, P. ChemMedChem 2014, 9, 2587.

    19. [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].

    20. [20]

      [20] Alphen, J. V. Recl. Trav. Chim. Pays-Bas 1929, 48, 417.

    21. [21]

      [21] Ahn, S. H.; Jang, S. S.; Kim, Y. K.; Lee, K. J. Bull. Korean Chem. Soc. 2012, 33, 233.

    22. [22]

      [22] Weissgerber; Kruber Chem. Ber. 1920, 53, 1564.

  • 加载中
    1. [1]

      Jing WUPuzhen HUIHuilin ZHENGPingchuan YUANChunfei WANGHui WANGXiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278

    2. [2]

      Xinting XIONGZhiqiang XIONGPanlei XIAOXuliang NIEXiuying SONGXiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145

    3. [3]

      Xiaoling LUOPintian ZOUXiaoyan WANGZheng LIUXiangfei KONGQun TANGSheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271

    4. [4]

      Hongjie SHENHaozhe MIAOYuhe YANGYinghua LIDeguang HUANGXiaofeng ZHANG . Synthesis, crystal structure, and fluorescence properties of two Cu(Ⅰ) complexes based on pyridyl ligand. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 855-863. doi: 10.11862/CJIC.20250009

    5. [5]

      Jingjing QINGFan HEZhihui LIUShuaipeng HOUYa LIUYifan JIANGMengting TANLifang HEFuxing ZHANGXiaoming ZHU . Synthesis, structure, and anticancer activity of two complexes of dimethylglyoxime organotin. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1301-1308. doi: 10.11862/CJIC.20240003

    6. [6]

      Hexing SONGZan SUN . Synthesis, crystal structure, Hirshfeld surface analysis, and fluorescent sensing for Fe3+ of an Mn(Ⅱ) complex based on 1-naphthalic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 885-892. doi: 10.11862/CJIC.20240402

    7. [7]

      Yahui HANJinjin ZHAONing RENJianjun ZHANG . Synthesis, crystal structure, thermal decomposition mechanism, and fluorescence properties of benzoic acid and 4-hydroxy-2, 2′: 6′, 2″-terpyridine lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 969-982. doi: 10.11862/CJIC.20240395

    8. [8]

      Yuxin CHENYanni LINGYuqing YAOKeyi WANGLinna LIXin ZHANGQin WANGHongdao LIWenmin WANG . Construction, structures, and interaction with DNA of two Sm4 complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(6): 1141-1150. doi: 10.11862/CJIC.20240258

    9. [9]

      Linjie ZHUXufeng LIU . Synthesis, characterization and electrocatalytic hydrogen evolution of two di-iron complexes containing a phosphine ligand with a pendant amine. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 939-947. doi: 10.11862/CJIC.20240416

    10. [10]

      Yingchun ZHANGYiwei SHIRuijie YANGXin WANGZhiguo SONGMin WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078

    11. [11]

      Yan Liu Yuexiang Zhu Luhua Lai . Introduction to Blended and Small-Class Teaching in Structural Chemistry: Exploring the Structure and Properties of Crystals. University Chemistry, 2024, 39(3): 1-4. doi: 10.3866/PKU.DXHX202306084

    12. [12]

      Jiaming Xu Yu Xiang Weisheng Lin Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093

    13. [13]

      Haitang WANGYanni LINGXiaqing MAYuxin CHENRui ZHANGKeyi WANGYing ZHANGWenmin WANG . Construction, crystal structures, and biological activities of two Ln3 complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1474-1482. doi: 10.11862/CJIC.20240188

    14. [14]

      Weina Wang Fengyi Liu Wenliang Wang . “Extracting Commonality, Delving into Typicals, Deriving Individuality”: Constructing a Knowledge Graph of Crystal Structures. University Chemistry, 2024, 39(3): 36-42. doi: 10.3866/PKU.DXHX202308029

    15. [15]

      Junqiao Zhuo Xinchen Huang Qi Wang . Symbol Representation of the Packing-Filling Model of the Crystal Structure and Its Application. University Chemistry, 2024, 39(3): 70-77. doi: 10.3866/PKU.DXHX202311100

    16. [16]

      Changqing MIAOFengjiao CHENWenyu LIShujie WEIYuqing YAOKeyi WANGNi WANGXiaoyan XINMing FANG . Crystal structures, DNA action, and antibacterial activities of three tetranuclear lanthanide-based complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2455-2465. doi: 10.11862/CJIC.20240192

    17. [17]

      Wenyan Dan Weijie Li Xiaogang Wang . The Technical Analysis of Visual Software ShelXle for Refinement of Small Molecular Crystal Structure. University Chemistry, 2024, 39(3): 63-69. doi: 10.3866/PKU.DXHX202302060

    18. [18]

      Yongzhi LIHan ZHANGGangding WANGYanwei SUILei HOUYaoyu WANG . A two-dimensional metal-organic framework for the determination of nitrofurantoin and nitrofurazone in aqueous solution. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 245-253. doi: 10.11862/CJIC.20240307

    19. [19]

      Caixia Lin Zhaojiang Shi Yi Yu Jianfeng Yan Keyin Ye Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005

    20. [20]

      Xin MAYa SUNNa SUNQian KANGJiajia ZHANGRuitao ZHUXiaoli GAO . A Tb2 complex based on polydentate Schiff base: Crystal structure, fluorescence properties, and biological activity. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1347-1356. doi: 10.11862/CJIC.20230357

Metrics
  • PDF Downloads(0)
  • Abstract views(1147)
  • HTML views(102)

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

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return