Citation: Tian-Cai Li, Cou-Xi Chen, Xue-Qiang Li, Xiao-Hui Gao. Selective amination of the mucohalic acid derivatives[J]. Chinese Chemical Letters, ;2013, 24(3): 202-204. shu

Selective amination of the mucohalic acid derivatives

  • Corresponding author: Xue-Qiang Li, 
  • Received Date: 9 November 2012
    Available Online: 5 January 2013

  • An efficient synthesis of 4,5-diamino-3-halofuran-2(5H)-ones has been developed based on a sequential acylation and bisamination of mucohalic acids. The β-and γ-amination products have also been prepared with high regioselectivity. This reaction shows some advantages in terms of its simple operation and readily available but highly functionalized starting material. All products gave satisfactory IR, 1H NMR, 13C NMR and HRMS.
  • 加载中
    1. [1]

      [1] (a) S.L. Midland, N.T. Keen, J.J. Sims, Secosyrins 1 and 2 and syributins 1 and 2: novel structures produced by bacteria expressing the avrD gene, J. Org. Chem. 60 (1995) 1118-1119;

    2. [2]

      (b) S. Miao, R.J. Andersen, A.H. Rubrolides, metabolites of the colonial tunicate Ritterella rubra, J. Org. Chem. 56 (1991) 6275-6280;

    3. [3]

      (c) M.J. Ortega, E. Zubia, J.M. Ocaña, S. Naranjo, J. Salvá, New Rubrolides from the Ascidian Synoicum blochmanni, Tetrahedron 56 (2000) 3963-3967;

    4. [4]

      (d) M. Renard, L.A. Ghosez, A convergent asymmetric synthesis of γ-butenolides, Tetrahedron 57 (2001) 2597-2608;

    5. [5]

      (e) C. Dehoux, L. Gorrichon, M. Baltas, Stereoselective preparation of protected thymine polyoxin C and approaches towards synthesis of its C2'-modified analogues, Eur. J. Org. Chem. 6 (2001) 1105-1113;

    6. [6]

      (f) J. Jauch, A short total synthesis of Kuehneromycin A, Angew. Chem. Int. Ed. 39 (2000) 2764-2765;

    7. [7]

      (g) T.E. Kedar, M.W. Miller, L.S. Hegedus, Synthesis of 4-alkyl-4-alkoxybutenolides having unsaturated side chains via chromium carbene complex photochemistry: (+)-cerulenin, J. Org. Chem. 61 (1996) 6121-6126;

    8. [8]

      (h) S.P. Brown, N.C. Goodwin, D.W.C. MacMillan, The first enantio-selective organocatalytic Mukaiyama-Michael reaction: a direct method for the synthesis of enantioenriched g-butenolide architecture, J. Am. Chem. Soc. 125 (2003) 1192-1194;

    9. [9]

      (i) G.R. Flematti, E.L. Ghisalberti, K.W. Dixon, R.D. Trengove, A compound from smoke that promotes seed germination, Science 305 (2004) 977;

    10. [10]

      (j) G.R. Flematti, E.L. Ghisalberti, K.W. Dixon, R.D. Trengove, Identification of alkyl substituted 2H-furo[2,3-c]pyran-2-ones as germination stimulants present in smoke, J. Agric. Food Chem. 57 (2009) 9475-9480;

    11. [11]

      (k) Y. Yaguchi, A. Nakahashi, N. Miura, et al., Stereochemical study of chiral tautomeric flavorous furanones by vibrational circular dichroism, Org. Lett. 10 (2008) 4883-4885.

    12. [12]

      [2] S.M. Ma, B. Wu, Z.J. Shi, An efficient synthesis of 4-halo-5-hydroxy-furan-2(5H)-ones via the sequential halolactonization and γ-hydroxylation of 4-aryl-2,3-alkadienoic acids, J. Org. Chem. 69 (2004) 1429-1431.

    13. [13]

      [3] (a) H.W. Moore, L.J. Hernandez, D.M. Kunert, F. Mercer, A. Sing, A new synthetic route to 2-azetidinones. Ring contraction of 4-azido-2-pyrrolin-ones to 3-cyano-2-azetidinones, J. Am. Chem. Soc. 103 (1981) 1769-1777;

    14. [14]

      (b) Q.H. Chen, Z. Geng, B. Huang, Synthesis of enantiomerically pure 5-(l-menthyloxy)-3,4-dibromo-2(5H)-furanone and its tandem asymmetric Michael additionelimination reaction, Tetrahedron: Asymmetry 6 (1995) 401-404;

    15. [15]

      (c) G.A. Sulikowski, F. Agnelli, R.M. Corbett, Investigations into a biomimetic approach toward CP-225 917 and CP-263,114, J. Org. Chem. 65 (2000) 337-342;

    16. [16]

      (d) J. Zhang, P.G. Blazecka, D. Belmont, J.G. Davidson, Reinvestigation of mucohalic acids, versatile and useful building blocks for highly functionalized α, β-unsaturated γ-butyrolactones, Org. Lett. 4 (2002) 4559-4561;

    17. [17]

      (e) J. Zhang, P.G. Blazecka, J.G. Davidson, First direct reductive amination of mucochloric acid: a simple and efficient method for preparing highly functionalized α, β-unsaturated γ-butyrolactams, Org. Lett. 5 (2003) 553-556;

    18. [18]

      (f) J. Zhang, P.G. Blazecka, H. Berven, D. Belmont, Metal-mediated allylation of mucohalic acids: facile formation of γ-allylic α, β-unsaturated g-butyrolactones, Tetrahedron Lett. 44 (2003) 5579-5582;

    19. [19]

      (g) J. Zhang, K.D. Sarma, T.T. Curran, D.T. Belmont, J.G. Davidson, Efficient synthesis of novel g-substituted g-butenolides by Lewis acid catalyzed addition of metal enolates of active methylene compounds to mucohalic acids, J. Org. Chem. 70 (2005) 5890-5895.

    20. [20]

      [4] P.G. Blazecka, D. Belmont, T. Curran, D. Pflum, J. Zhang, Further utilization of mucohalic acids: palladium-free, regioselective etherification and amination of α, β-dihalo γ-methoxycarbonyloxy and γ-acetoxy butenolides, Org. Lett. 5 (2003) 5015-5017.

    21. [21]

      [5] (a) G.A. Taylor, Mucobromic acid, Org. Synth. 4 (1963) 688;

    22. [22]

      (b) M.X. Wei, L. Feng, X.Q. Li, X.Z. Zhou, Z.H. Shao, Synthesis of new chiral 2,5-disubstituted 1,3,4-thiadiazoles possessing γ-butenolide moiety and preliminary evaluation of in vitro anticancer activity, Eur. J. Med. Chem. 44 (2009) 3340-3344;

    23. [23]

      (c) F. Ma, L.Q. Li, H.E. Hao, Y. Su, W.Y. Liu, Activated carbon supported sulfuric acid as an efficient catalyst for Cross-Aldol condensation of ketones with aromatic aldehydes under solvent-free conditions, Chin. J. Org. Chem. 30 (2010) 419-423;

    24. [24]

      (d) H.Y. Chu, H.F. Zhang, J.H. Yang, et al., Catalytic synthesis of 14-alkyl(aryl)-14Hdibenzo[a,j]xanthene compounds by the H2SO4 loaded coal based activated carbon as solid acid catalyst under solvent-free condition, Chin, J. Org. Chem. 29 (2009) 1637-1639.

    25. [25]

      [6] K. Jahnisch, W. Duczek, Zur Chemie der Mucohalogensauren. Ⅳ [Ⅰ] Reaktionen von Mucochlorsaurederivaten mit Anilin, J. Prakt. Chem. (Leipzig) 332 (1990) 117-121.

  • 加载中
    1. [1]

      Hui LiYanxing QiJia ChenJuanjuan WangMin YangHongdeng Qiu . Synthesis of amine-pillar[5]arene porous adsorbent for adsorption of CO2 and selectivity over N2 and CH4. Chinese Chemical Letters, 2024, 35(11): 109659-. doi: 10.1016/j.cclet.2024.109659

    2. [2]

      Wen-Tao OuyangJun JiangYan-Fang JiangTing LiYuan-Yuan LiuHong-Tao JiLi-Juan OuWei-Min He . Sono-photocatalytic amination of quinoxalin-2(1H)-ones with aliphatic amines. Chinese Chemical Letters, 2024, 35(10): 110038-. doi: 10.1016/j.cclet.2024.110038

    3. [3]

      Dong-Xue Jiao Hui-Li Zhang Chao He Si-Yu Chen Ke Wang Xiao-Han Zhang Li Wei Qi Wei . Layered (C5H6ON)2[Sb2O(C2O4)3] with a large birefringence derived from the uniform arrangement of π-conjugated units. Chinese Journal of Structural Chemistry, 2024, 43(6): 100304-100304. doi: 10.1016/j.cjsc.2024.100304

    4. [4]

      Bairu MengZongji ZhuoHan YuSining TaoZixuan ChenErik De ClercqChristophe PannecouqueDongwei KangPeng ZhanXinyong Liu . Design, synthesis, and biological evaluation of benzo[4,5]thieno[2,3-d]pyrimidine derivatives as novel HIV-1 NNRTIs. Chinese Chemical Letters, 2024, 35(6): 108827-. doi: 10.1016/j.cclet.2023.108827

    5. [5]

      You ZhouLi-Sheng WangShuang-Gui LeiBo-Cheng TangZhi-Cheng YuXing LiYan-Dong WuKai-Lu ZhengAn-Xin Wu . I2-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations. Chinese Chemical Letters, 2025, 36(1): 109799-. doi: 10.1016/j.cclet.2024.109799

    6. [6]

      Peiyan ZhuYanyan YangHui LiJinhua WangShiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533

    7. [7]

      Gang HuChun WangQinqin WangMingyuan ZhuLihua Kang . The controlled oxidation states of the H4PMo11VO40 catalyst induced by plasma for the selective oxidation of methacrolein. Chinese Chemical Letters, 2025, 36(2): 110298-. doi: 10.1016/j.cclet.2024.110298

    8. [8]

      Haoran ShiJiaxin WangYuqin ZhuHongyang LiGuodong JuLanlan ZhangChao Wang . Highly selective α-C(sp3)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333

    9. [9]

      Xiuzheng DengChanghai LiuXiaotong YanJingshan FanQian LiangZhongyu Li . Carbon dots anchored NiAl-LDH@In2O3 hierarchical nanotubes for promoting selective CO2 photoreduction into CH4. Chinese Chemical Letters, 2024, 35(6): 108942-. doi: 10.1016/j.cclet.2023.108942

    10. [10]

      Xiao-Ming ChenLianhui SongJun PanFei ZengYi XieWei WeiDong Yi . Visible-light-induced four-component difunctionalization of alkenes to construct phosphorodithioate-containing quinoxalin-2(1H)-ones. Chinese Chemical Letters, 2024, 35(11): 110112-. doi: 10.1016/j.cclet.2024.110112

    11. [11]

      Hualin JiangWenxi YeHuitao ZhenXubiao LuoVyacheslav FominskiLong YePinghua Chen . Novel 3D-on-2D g-C3N4/AgI.x.y heterojunction photocatalyst for simultaneous and stoichiometric production of H2 and H2O2 from water splitting under visible light. Chinese Chemical Letters, 2025, 36(2): 109984-. doi: 10.1016/j.cclet.2024.109984

    12. [12]

      Ke-Ai Zhou Lian Huang Xing-Ping Fu Li-Ling Zhang Yu-Ling Wang Qing-Yan Liu . Fluorinated metal-organic framework for methane purification from a ternary CH4/C2H6/C3H8 mixture. Chinese Journal of Structural Chemistry, 2023, 42(11): 100172-100172. doi: 10.1016/j.cjsc.2023.100172

    13. [13]

      Tong LiLeping PanYan ZhangJihu SuKai LiKuiliang LiHu ChenQi SunZhiyong Wang . Electrochemical construction of 2,5-diaryloxazoles via N–H and C(sp3)-H functionalization. Chinese Chemical Letters, 2024, 35(4): 108897-. doi: 10.1016/j.cclet.2023.108897

    14. [14]

      Jian Yang Guang Yang Zhijie Chen . Capturing carbon dioxide from air by using amine-functionalized metal-organic frameworks. Chinese Journal of Structural Chemistry, 2024, 43(5): 100267-100267. doi: 10.1016/j.cjsc.2024.100267

    15. [15]

      Tong Zhou Xue Liu Liang Zhao Mingtao Qiao Wanying Lei . Efficient Photocatalytic H2O2 Production and Cr(VI) Reduction over a Hierarchical Ti3C2/In4SnS8 Schottky Junction. Acta Physico-Chimica Sinica, 2024, 40(10): 2309020-. doi: 10.3866/PKU.WHXB202309020

    16. [16]

      Chong-Yang ShiJian-Xing GongZhen LiChao ShuLong-Wu YeQing SunBo ZhouXin-Qi Zhu . Gold-catalyzed intermolecular amination of allyl azides with ynamides: Efficient construction of 3-azabicyclo[3.1.0] scaffold. Chinese Chemical Letters, 2025, 36(2): 109895-. doi: 10.1016/j.cclet.2024.109895

    17. [17]

      Wei Zhong Dan Zheng Yuanxin Ou Aiyun Meng Yaorong Su . K原子掺杂高度面间结晶的g-C3N4光催化剂及其高效H2O2光合成. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-. doi: 10.3866/PKU.WHXB202406005

    18. [18]

      Guoqiang Chen Zixuan Zheng Wei Zhong Guohong Wang Xinhe Wu . 熔融中间体运输导向合成富氨基g-C3N4纳米片用于高效光催化产H2O2. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-. doi: 10.3866/PKU.WHXB202406021

    19. [19]

      Chao LIUJiang WUZhaolei JIN . Synthesis, crystal structures, and antibacterial activities of two zinc(Ⅱ) complexes bearing 5-phenyl-1H-pyrazole group. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1986-1994. doi: 10.11862/CJIC.20240153

    20. [20]

      Yang LiuYan LiuKaiyin YangZhiruo ZhangWenbo ZhangBingyou YangHua LiLixia Chen . A selective HK2 degrader suppresses SW480 cancer cell growth by degrading HK2. Chinese Chemical Letters, 2024, 35(8): 109264-. doi: 10.1016/j.cclet.2023.109264

Metrics
  • PDF Downloads(0)
  • Abstract views(608)
  • HTML views(6)

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