Citation: Soliman Hanan A., Khatab Tamer K., Abdel-Megeid Farouk M. E. . Utilization of bromine azide to access vicinal-azidobromides from arylidene malononitrile[J]. Chinese Chemical Letters, ;2016, 27(9): 1515-1518. doi: 10.1016/j.cclet.2016.03.026 shu

Utilization of bromine azide to access vicinal-azidobromides from arylidene malononitrile

  • Corresponding author: Soliman Hanan A., tarek12_2@yahoo.com
  • Received Date: 24 January 2016
    Revised Date: 15 March 2016
    Accepted Date: 16 March 2016
    Available Online: 24 September 2016

Figures(5)

  • An efficient and facile approach for tetrachlorosilane as an in situ mediated transformation via a one-pot, synthesis of vicinal bromoazides through the generation of BrN3 from azidochlorosilane and N-bromosuccinimide in acetonitrile as solvent at ambient temperature is achieved. This catalytic process represents a highly regioselective and high yielding method for the synthesis of 1, 2-bromoazides. Thiamine pyrophosphate (TPP) riboswitches regulate essential genes in bacteria by changing conformation upon binding intracellular TPP. Molecular docking studies are conducted to understand the orientation and the interaction of each synthesized molecules with TPP riboswitches. 2016 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.
  • 加载中
    1. [1]

      Bauer S.H.. An electron diffraction investigation of the structure of difluorodiazine[J]. J. Am. Chem. Soc., 1947,69:3104-3108. doi: 10.1021/ja01204a053

    2. [2]

      Dehnicke K.. Reactions of halogen azides[J]. Angew. Chem. Int. Ed. Engl., 1967,6:240-246. doi: 10.1002/(ISSN)1521-3773

    3. [3]

      (a) A. Hassner, F. Boerwinkle, Ionic and free-radical addition of bromine azide to olefins, J. Am. Chem. Soc. 90(1968) 216-218;
      (b) F. Boerwinkle, A. Hassner, Solvent participation in additions to olefin, Tetrahedron Lett. 9(1968) 39213924;
      (c) A. Hassner, F. Boerwinkle, Free radical vs ionic additions of halogen azides to olefins, Tetrahedron Lett. 10(1969) 3309-3319.

    4. [4]

      Hassner A., Teeter J.S.. Stereochemistry. LIV. Phenyl migration in pseudo halogen additions to 3, 3, 3-triphenylpropene[J]. J. Org. Chem., 1970,35:3397-3401. doi: 10.1021/jo00835a046

    5. [5]

      Hassner A.. Regiospecific and stereospecific introduction of azide functions into organic molecules[J]. Acc. Chem. Res., 1971,4:9-16. doi: 10.1021/ar50037a002

    6. [6]

      L'Abbe G., Hassner A.. Synthesis of a-azidovinyl ketones from the iodine azide adducts of a, b-unsaturated ketones[J]. J. Org. Chem., 1971,36:258-260. doi: 10.1021/jo00801a004

    7. [7]

      L'Abbé G., Hassner A.. Neue methoden zur darstellung von vinylaziden[J]. Angew. Chem. Int. Ed. Engl., 1971,10:98-104. doi: 10.1002/anie.197100981

    8. [8]

      Hassner A., Keogh J.. Addition of halogen azides to non-cyclic conjugated dienes[J]. Tetrahedron Lett., 1975,16:1575-1578. doi: 10.1016/S0040-4039(00)72201-5

    9. [9]

      Ponsold K., Wunderwald M.. Gekoppelte additionsreaktionen an 14, 15-ungesättigten androstanen einfluß des positiven halogens auf die regioselektivität[J]. J. Prakt. Chem. (Leipzig), 1983,325:123-132. doi: 10.1002/prac.19833250115

    10. [10]

      Nagorski R.W., Brown R.S.. Electrophilic addition of bromine to olefins in the presence of nucleophilic trapping anions. Implications for the lifetimes of bromonium ion intermediates produced from electrophilic bromination of olefins in methanol[J]. J. Am. Chem. Soc., 1992,114:7773-7779. doi: 10.1021/ja00046a024

    11. [11]

      Van Ende D., Krief A.. A new reagent for stereospecific synthesis of aziridines from olefins[J]. Angew. Chem. Int. Ed. Engl., 1974,13:279-280.  

    12. [12]

      Denis J.N., Krief A.. New synthetic route to 9, 10-imino-phenanthrene[J]. Tetrahedron, 1979,35:2901-2903. doi: 10.1016/S0040-4020(01)99506-7

    13. [13]

      Chiu I.C., Kohn H.. Syntheses and reactivity of trans-6-azabicyclo[3.1.0] hexan-2-ol derivatives and indanol[1, 2-b]aziridine. Structural analogs of mitomycin C[J]. J. Org. Chem., 1983,48:2857-2866. doi: 10.1021/jo00165a015

    14. [14]

      Nguy N.M., Chiu I.C., Kohn H.. Synthesis and reactivity of 6-and 7-methoxyindano[1, 2-b]aziridines[J]. J. Org. Chem., 1987,52:1649-1655. doi: 10.1021/jo00385a001

    15. [15]

      Lange W., Tueckmantel W.. Synthesis and reactions of oligomethylene-clamped 1 H-azepines and benzene imines. Their valence tautomeric equilibrium and nitrogen stereochemistry[J]. Chem. Ber., 1989,122:1765-1976. doi: 10.1002/(ISSN)1099-0682

    16. [16]

      Devalankar D.A., Sudalai A.. A concise synthesis of (+)-deoxoprosophylline via Co(Ⅲ)(salen)-catalyzed two stereocentered HKR of racemic azido epoxides[J]. Tetrahedron Lett., 2012,53:3213-3215. doi: 10.1016/j.tetlet.2012.04.067

    17. [17]

      Saikia I., Phukan P.C.. Catalyst-free vicinal bromoazidation of olefins using TMSN3 and NBS[J]. C.R. Chim., 2012,15:688-692. doi: 10.1016/j.crci.2012.05.001

    18. [18]

      Hajra S., Sinha D., Bhowmick M.. Metal triflate catalyzed highly regio-and stereoselective 1, 2-bromoazidation of alkenes using NBS and TMSN3 as the bromine and azide sources[J]. Tetrahedron Lett., 2006,47:7017-7019. doi: 10.1016/j.tetlet.2006.07.110

    19. [19]

      Hajra S., Sinha D., Bhowmick M.. Metal triflate catalyzed reactions of alkenes, NBS, nitriles, and TMSN3:synthesis of 1, 5-disubstituted tetrazoles[J]. J. Org. Chem., 2007,72:1852-1855. doi: 10.1021/jo062432j

    20. [20]

      Hajra S., Bhowmick M., Sinha D.. Highly regio-and stereoselective asymmetric bromoazidation of chiral a, b-unsaturated carboxylic acid derivatives:scope and limitations[J]. J. Org. Chem., 2006,71:9237-9240. doi: 10.1021/jo061593k

    21. [21]

      Saikia I., Phukan P.. Facile generation of vicinal bromoazides from olefins using TMSN3 and TsNBr2 without any catalyst[J]. Tetrahedron Lett., 2009,50:5083-5087. doi: 10.1016/j.tetlet.2009.06.059

    22. [22]

      Kumar A., Rao M.S., Mehta V.. A simple and efficient bromoazidation of alkenes using PTT and TMSN3 in ionic liquid[J]. Indian, J. Chem., Sect. B:Org. Chem. Incl. Med. Chem., 2011,50B:1123-1127.  

    23. [23]

      Hassner A., Fowler F.W.. General synthesis of vinyl azides from olefins. Stereochemistry of elimination from b-iodo azides[J]. J. Org. Chem., 1968,33:2686-2691. doi: 10.1021/jo01271a016

    24. [24]

      Wasserman H.H., Brunner R.K., Buynak J.D.. Total synthesis of (±)-Omethylorantine[J]. J. Am. Chem. Soc., 1985,107:519-521. doi: 10.1021/ja00288a050

    25. [25]

      (a) S. Ranganathan, D. Ranganathan, A.K. Mehrotra, The "Hassner-Ritter" reaction in iodine azide additions to pinenes with solvent participation, Tetrahedron Lett. 14(1973) 2265-2266;
      (b) S.N. Moorthy, D. Devaprabakara, Addition of iodine azide to C-9 and C-10 medium-ring dienes, Tetrahedron Lett. 16(1975) 257-260.

    26. [26]

      (a) D. Van Ende, A. Krief, A highly potent reagent for regioselective and stereospecific synthesis of polyenes bearing terminal aziridine groups, Angew. Chem. Int. Ed. Engl. 13(1974) 279-280;
      (b) J.N. Denis, A. Krief, New synthetic route to 9, 10-imino-phenanthrene 1, Tetrahedron 35(1979) 2901-2903.

    27. [27]

      Rossi S., Benaglia M., Genoni A.. Organic reactions mediated by tetrachlorosilane[J]. Tetrahedron, 2014,70:2065-2080. doi: 10.1016/j.tet.2014.01.055

    28. [28]

      (a) H.A. Soliman, T.K. Khtab, Efficient heterogeneous catalytic one-pot, three component synthesis of γ-hydroxy-β-ketoamide, Egypt J. Chem. 57(2014) 129-142;
      (b) T.K. Khatab, K.A.M. El-Bayouki, W.M. Basyouni, A new and facile tetrachlorosilane-promoted one-pot condensation for the synthesis of a novel series of tetracyclic 1, 5-thiazepines, Tetrahedron Lett. 55(2014) 6039-6041;
      (c) H.A. Soliman, T.A. Salama, Silicon-mediated highly efficient synthesis of 1, 8-dioxo-octahydroxanthenes and their transformation to novel functionalized pyrano-tetrazolo[1, 5-a] azepine derivatives, Chin. Chem. Lett. 24(2013) 404-406;
      (d) T.K. Khatab, K.A.M. El-Bayouki, W.M. Basyouni, An efficient synthesis of b-acylureas via a three-component, one-potsynthesis using TCS/ZnCl2, Tetrahedron Lett. 52(2011) 1448-1451;
      (e) D.S. Badawy, E. Abdel-Galil, E.M. Kandeel, W.M. Basyouni, T.K. Khatab, Tetrachlorosilane-zinc chloride as a new potent binary reagent for one-pot, threecomponent synthesis of Mannich-type products, Phosphorus Sulfur Silicon Relat. Elem. 184(2009) 2799-2812;
      (f) S.S. Elmorsy, D.S. Badawy, T.K. Khatab, Chemoselective bromination in a twostep substitution under the influence of tetrachlorosilane and N-bromosuccinimide, Phosphorus Sulfur Silicon Relat. Elem. 181(2006) 2005-2012.

    29. [29]

      (a) H.A. Soliman, A.Y. Mubarak, S.S. Elmorsy, An efficient synthesis of bis(indolyl) methanes and N, N'-alkylidene 4 bisamides by Silzic under solvent free conditions, Chin. Chem. Lett. 27(2016) 353-356;
      (b) H.A. Soliman, A.Y. Mubarak, A. El-Mekabati, H.M. Awad, S.S. Elmorsy, Ecofriendly synthesis of amidochloroalkyl naphthols, cyclization of the product to oxazepinones for biological evaluation, Monatsh Chem. 147(2016) 809-816;
      (c) H.A. Soliman, A.Y. Mubarak, A. El-Mekabati, S.S. Elmorsy, SiO2/ZnCl2-catalyzed heterocyclic synthesis:green, rapid and efficient one-pot synthesis of 14-H-dibenzo[a, j]xanthenes, 1, 8-dioxo-octahydroxanthenes and 1, 8-dioxo-decahydroacridines under solvent-free conditions, Chem. Sci. Trans. 3(2014) 819-825.

    30. [30]

      Olah G.A., Wang Q., Li X.Y., Prakash G.K.S.. Azidobromination of alkenes with azidotrimethylsilane/n-bromosuccinimide 1[J]. Synlett, 1990:487-489.  

    31. [31]

      (a) R.A. Valiulin, S. Mamidyala, M.G. Finn, Taming chlorine azide:access to 1, 2-azidochlorides from alkenes, J. Org. Chem. 80(2015) 2740-2755;
      (b) D. Cantillo, B. Gutmann, C.O. Kappe, Safe generation and use of bromine azide under continuous flow conditions-selective 1, 2-bromoazidation of olefins, Org. Biomol. Chem. 14(2016) 853-857.

    32. [32]

      The Molecular Operating E, Chemical Computing Group I, Montreal, QC, 2015.

    33. [33]

      Warner K.D., Homan P., Weeks K.M.. Validating fragment-based drug discovery for biological RNAs:lead fragments bind and remodel the TPP riboswitch specifically[J]. Chem. Biol., 2014,21:591-595. doi: 10.1016/j.chembiol.2014.03.007

  • 加载中
    1. [1]

      Fanjun KongYixin GeShi TaoZhengqiu YuanChen LuZhida HanLianghao YuBin Qian . Engineering and understanding SnS0.5Se0.5@N/S/Se triple-doped carbon nanofibers for enhanced sodium-ion batteries. Chinese Chemical Letters, 2024, 35(4): 108552-. doi: 10.1016/j.cclet.2023.108552

    2. [2]

      Hui WangHaodong JiDandan ZhangXudong YangHanchun ChenChunqian JiangWeiliang SunJun DuanWen Liu . Solar-light-driven photocatalytic degradation and detoxification of ciprofloxacin using sodium niobate nanocubes decorated g-C3N4 with built-in electric field. Chinese Chemical Letters, 2025, 36(5): 110200-. doi: 10.1016/j.cclet.2024.110200

    3. [3]

      Haiying Lu Weijie Li . The electrolyte solvation and interfacial chemistry for anode-free sodium metal batteries. Chinese Journal of Structural Chemistry, 2024, 43(11): 100334-100334. doi: 10.1016/j.cjsc.2024.100334

    4. [4]

      Shengyu ZhaoQinhao ShiWuliang FengYang LiuXinxin YangXingli ZouXionggang LuYufeng Zhao . Suppression of multistep phase transitions of O3-type cathode for sodium-ion batteries. Chinese Chemical Letters, 2024, 35(5): 108606-. doi: 10.1016/j.cclet.2023.108606

    5. [5]

      Xiping DongXuan WangZhixiu LuQinhao ShiZhengyi YangXuan YuWuliang FengXingli ZouYang LiuYufeng Zhao . Construction of Cu-Zn Co-doped layered materials for sodium-ion batteries with high cycle stability. Chinese Chemical Letters, 2024, 35(5): 108605-. doi: 10.1016/j.cclet.2023.108605

    6. [6]

      Fabrice Nelly HabarugiraDucheng YaoWei MiaoChengcheng ChuZhong ChenShun Mao . Synergy of sodium doping and nitrogen defects in carbon nitride for promoted photocatalytic synthesis of hydrogen peroxide. Chinese Chemical Letters, 2024, 35(8): 109886-. doi: 10.1016/j.cclet.2024.109886

    7. [7]

      Mingxin SongLijing XieFangyuan SuZonglin YiQuangui GuoCheng-Meng Chen . New insights into the effect of hard carbons microstructure on the diffusion of sodium ions into closed pores. Chinese Chemical Letters, 2024, 35(6): 109266-. doi: 10.1016/j.cclet.2023.109266

    8. [8]

      Zhijia ZhangShihao SunYuefang ChenYanhao WeiMengmeng ZhangChunsheng LiYan SunShaofei ZhangYong Jiang . Epitaxial growth of Cu2-xSe on Cu (220) crystal plane as high property anode for sodium storage. Chinese Chemical Letters, 2024, 35(7): 108922-. doi: 10.1016/j.cclet.2023.108922

    9. [9]

      Jun-Ming CaoKai-Yang ZhangJia-Lin YangZhen-Yi GuXing-Long Wu . Differential bonding behaviors of sodium/potassium-ion storage in sawdust waste carbon derivatives. Chinese Chemical Letters, 2024, 35(4): 109304-. doi: 10.1016/j.cclet.2023.109304

    10. [10]

      Shengyu ZhaoXuan YuYufeng Zhao . A water-stable high-voltage P3-type cathode for sodium-ion batteries. Chinese Chemical Letters, 2024, 35(9): 109933-. doi: 10.1016/j.cclet.2024.109933

    11. [11]

      Changyuan BaoYunpeng JiangHaoyin ZhongHuaizheng RenJunhui WangBinbin LiuQi ZhaoFan JinYan Meng ChongJianguo SunFei WangBo WangXimeng LiuDianlong WangJohn Wang . Synergizing 3D-printed structure and sodiophilic interface enables highly efficient sodium metal anodes. Chinese Chemical Letters, 2024, 35(11): 109353-. doi: 10.1016/j.cclet.2023.109353

    12. [12]

      Fan WuShaoyang WuXin YeYurong RenPeng Wei . Research progress of high-entropy cathode materials for sodium-ion batteries. Chinese Chemical Letters, 2025, 36(4): 109851-. doi: 10.1016/j.cclet.2024.109851

    13. [13]

      Xuan WangPeng SunSiteng YuanLu YueYufeng Zhao . P2-type low-cost and moisture-stable cathode for sodium-ion batteries. Chinese Chemical Letters, 2025, 36(5): 110015-. doi: 10.1016/j.cclet.2024.110015

    14. [14]

      Binyang QinMengqi WangShimei WuYining LiChilin LiuYufei ZhangHaosen Fan . Carbon dots confined nanosheets assembled NiCo2S4@CDs cross-stacked architecture for enhanced sodium ion storage. Chinese Chemical Letters, 2024, 35(7): 108921-. doi: 10.1016/j.cclet.2023.108921

    15. [15]

      Luyan ShiKe ZhuYuting YangQinrui LiangQimin PengShuqing ZhouTayirjan Taylor IsimjanXiulin Yang . Phytic acid-derivative Co2B-CoPOx coralloidal structure with delicate boron vacancy for enhanced hydrogen generation from sodium borohydride. Chinese Chemical Letters, 2024, 35(4): 109222-. doi: 10.1016/j.cclet.2023.109222

    16. [16]

      Dongmei DaiXiaobing LaiXiaojuan WangYunting YaoMengmin JiaLiang WangPengyao YanYaru QiaoZhuangzhuang ZhangBao LiDai-Huo Liu . Increasing (010) active plane of P2-type layered cathodes with hexagonal prism towards improved sodium-storage. Chinese Chemical Letters, 2024, 35(10): 109405-. doi: 10.1016/j.cclet.2023.109405

    17. [17]

      Jiaojiao LiangYouming PengZhichao XuYufei WangMenglong LiuXin LiuDi HuangYuehua WeiZengxi Wei . Boron/phosphorus co-doped nitrogen-rich carbon nanofiber with flexible anode for robust sodium-ion battery. Chinese Chemical Letters, 2025, 36(1): 110452-. doi: 10.1016/j.cclet.2024.110452

    18. [18]

      Huixin ChenChen ZhaoHongjun YueGuiming ZhongXiang HanLiang YinDing Chen . Unraveling the reaction mechanism of high reversible capacity CuP2/C anode with native oxidation POx component for sodium-ion batteries. Chinese Chemical Letters, 2025, 36(1): 109650-. doi: 10.1016/j.cclet.2024.109650

    19. [19]

      Ruofan YinZhaoxin GuoRui LiuXian-Sen Tao . Ultrafast synthesis of Na3V2(PO4)3 cathode for high performance sodium-ion batteries. Chinese Chemical Letters, 2025, 36(2): 109643-. doi: 10.1016/j.cclet.2024.109643

    20. [20]

      Yan-Jiang LiShu-Lei ChouYao Xiao . Detecting dynamic structural evolution based on in-situ high-energy X-ray diffraction technology for sodium layered oxide cathodes. Chinese Chemical Letters, 2025, 36(2): 110389-. doi: 10.1016/j.cclet.2024.110389

Metrics
  • PDF Downloads(1)
  • Abstract views(745)
  • HTML views(3)

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