Citation: Zinatossadat Hossaini, Faramarz Rostami-Charati, Mahboube Eslami Moghadam, Fatemeh Moghaddasi-Kochaksaraee. Expeditious solvent-free synthesis of 1, 3-thiazolanes via multicomponent reactions[J]. Chinese Chemical Letters, ;2014, 25(05): 794-796. doi: 10.1016/j.cclet.2014.02.002 shu

Expeditious solvent-free synthesis of 1, 3-thiazolanes via multicomponent reactions

  • Corresponding author: Zinatossadat Hossaini, 
  • Received Date: 18 November 2013
    Available Online: 9 February 2014

  • A series of 1,3-thiazolane derivatives have been synthesized via multicomponent reactions of activated acetylenes, primary amines and isothiocyanates in the presence of a catalytic amount of N-methylimidazole under solvent-free conditions.
  • 加载中
    1. [1]

      [1] A. Dömling, Isocyanide based multi component reactions in combinatorial chemistry, Comb. Chem. High Throughput Screening 1 (1998) 1-22.

    2. [2]

      [2] A. Dömling, I. Ugi, Multicomponent reactions with isocyanides, Angew. Chem. Int. Ed. 39 (2000) 3169-3210.

    3. [3]

      [3] L. Weber, Multi-component reactions and evolutionary chemistry, Drug Discov. Today 7 (2002) 143-147.

    4. [4]

      [4] A. Shaabani, A. Maleki, A.H. Rezayan, A. Sarvary, Recent progress of isocyanidebased multicomponent reactions in Iran, Mol. Divers. 15 (2011) 41-68.

    5. [5]

      [5] J. Zhu, H. Bienayme, Multicomponent Reactions, Wiley-VCH, Weinheim, Germany, 2005.

    6. [6]

      [6] P. Wipf, C. Kendall, Novel applications of alkenyl zirconocenes, Chem. Eur. J. 8 (2002) 1779-1784.

    7. [7]

      [7] G. Balme, E. Bossharth, N. Monteiro, Pd-assisted multicomponent synthesis of heterocycles, Eur. J. Org. Chem. (2003) 4101-4111.

    8. [8]

      [8] A. Jacobi von Wangelin, H. Neumann, D. Gordes, et al., Multicomponent coupling reactions of aldehydes and amides: an efficient tool for organic synthesis, Chem. Eur. J. 9 (2003) 4286-4294.

    9. [9]

      [9] (a) A. Domling, I. Ugi, Multicomponent reactions with isocyanides, Angew. Chem. Int. Ed. 39 (2000) 3168-3210; (b) I. Ugi, A. Domling, Multicomponent reactions in organic chemistry, Endeavour 18 (1994) 115-122; (c) S. Heck, A. Domling, A versatile multi-component one-pot thiazole synthesis, Synlett (2000) 424-426.

    10. [10]

      [10] L. Weber, The application of multi-component reactions in drug discovery, Curr. Med. Chem. 9 (2002) 2085-2093.

    11. [11]

      [11] I. Yavari, A.S. Shahvelayati, A. Malekafzali, Efficient synthesis of functionalized 2 4-diaminothiazoles from tetramethylguanidine, isothiocyanates, and a-bromoketones, J. Sulfur Chem. 31 (2010) 499-508.

    12. [12]

      [12] G.W.V. Cave, C.L. Raston, J.L. Scott, Recent advances in solventless synthesis with remarkable versatility, Chem. Commun. (2001) 2159-2169.

    13. [13]

      [13] R.A. Sheldon, Catalysis: the key to waste minimization, Chem. Ind. (1997) 12-15.

    14. [14]

      [14] G. Nagendrappa, Organic synthesis under solvent-free condition: an environmentally benign procedure, Resonance 7 (2002) 59-68.

    15. [15]

      [15] P.M. Dewick, Medicinal Natural Products: A Biosynthetic Approach, 2nd ed., Wiley, Chichester, UK, 2002.

    16. [16]

      [16] R. Breslow, On the mechanism of thiamine action. IV. Evidence from studies on model systems, J. Am. Chem. Soc. 80 (1958) 3719-3726.

    17. [17]

      [17] S. Miwatashi, Y. Arikawa, E. Kotani, et al., Novel Inhibitor of p38 MAP kinase as an anti-TNF-drug: discovery of N-[4-[2-ethyl-4-(3-methylphenyl)-1,3-thiazol-5- yl]-2-pyridyl]benzamide (TAK-715) as a potent and orally active anti-rheumatoid arthritis agent, J. Med. Chem. 48 (2005) 5966-5979.

    18. [18]

      [18] C. Papadopoulou, A. Geronikaki, D. Hadjipavlou-Litina, Synthesis and biological evaluation of new thiazolyl/benzothiazolyl-amides derivatives, Il Farmaco 60 (2005) 969-973.

    19. [19]

      [19] Y. Kumar, R. Green, K.Z. Borysko, et al., Synthesis of 2,4-disubstituted thiazoles and selenazoles as potential antitumor and antifilarial agents. 1. Methyl 4- (isothiocyanatomethyl)thiazole-2-carbamates-selenazole-2-carbamates, and related derivatives, J. Med. Chem. 36 (1993) 3843-3848.

    20. [20]

      [20] R. Pereira, C. Gaudon, B. Iglesias, et al., Synthesis of the PPAR-selective agonist GW501516 and C4-thiazole-substituted analogs, Bioorg. Med. Chem. Lett. 16 (2006) 49-54.

    21. [21]

      [21] Y. Tsurumi, H. Ueda, K. Hayashi, et al., WS75624 A and B, new endothelin converting enzyme inhibitors isolated from Saccharothrix sp. No. 75624, J. Antibiot. 48 (1995) 1066-1072.

    22. [22]

      [22] F.W. Bell, A.S. Cantrell, M. Hoberg, et al., Phenethylthiazolethiourea (PETT) compounds, a new class of HIV-1 reverse transcriptase inhibitors 1. Synthesis and basic structure-activity relationship studies of PETT analogs, J. Med. Chem. 38 (1995) 4929-4936.

    23. [23]

      [23] D.S. Millan, R.H. Prager, C. Brand, P.H. Hart, The synthesis and activity of oxazole and thiazole analogues of urocanic acid, Tetrahedron 56 (2000) 811-816.

    24. [24]

      [24] W.L. Wang, D.Y. Yao, M. Gu, et al., Synthesis and biological evaluation of novel bisheterocycle-containing compounds as potential anti-influenza virus agents, Bioorg. Med. Chem. Lett. 15 (2005) 5284.

  • 加载中
    1. [1]

      Meiling XuXinyang LiPengyuan LiuJunjun LiuXiao HanGuodong ChaiShuangling ZhongBai YangLiying Cui . A novel and visible ratiometric fluorescence determination of carbaryl based on red emissive carbon dots by a solvent-free method. Chinese Chemical Letters, 2025, 36(2): 109860-. doi: 10.1016/j.cclet.2024.109860

    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]

      Jun ZhangZhiyao ZhengCan Zhu . Stereochemical editing: Catalytic racemization of secondary alcohols and amines. Chinese Chemical Letters, 2024, 35(5): 109160-. doi: 10.1016/j.cclet.2023.109160

    4. [4]

      Wujun JianMong-Feng ChiouYajun LiHongli BaoSong Yang . Cu-catalyzed regioselective diborylation of 1,3-enynes for the efficient synthesis of 1,4-diborylated allenes. Chinese Chemical Letters, 2024, 35(5): 108980-. doi: 10.1016/j.cclet.2023.108980

    5. [5]

      Chunhua MaMengjiao LiuSiyu OuyangZhenwei CuiJingjing BiYuqin JiangZhiguo Zhang . Metal-free construction of diverse 1,2,4-triazolo[1,5-a]pyridines on water. Chinese Chemical Letters, 2025, 36(1): 109755-. doi: 10.1016/j.cclet.2024.109755

    6. [6]

      Xiaohui FuYanping ZhangJuan LiaoZhen-Hua WangYong YouJian-Qiang ZhaoMingqiang ZhouWei-Cheng Yuan . Palladium-catalyzed enantioselective decarboxylation of vinyl cyclic carbamates: Generation of amide-based aza-1,3-dipoles and application to asymmetric 1,3-dipolar cycloaddition. Chinese Chemical Letters, 2024, 35(12): 109688-. doi: 10.1016/j.cclet.2024.109688

    7. [7]

      Liangfeng YangLiang ZengYanping ZhuQiuan WangJinheng Li . Copper-catalyzed photoredox 1,4-amidocyanation of 1,3-enynes with N-amidopyridin-1-ium salts and TMSCN: Facile access to α-amido allenyl nitriles. Chinese Chemical Letters, 2024, 35(11): 109685-. doi: 10.1016/j.cclet.2024.109685

    8. [8]

      Huijie AnChen YangZhihui JiangJunjie YuanZhongming QiuLonghao ChenXin ChenMutu HuangLinlang HuangHongju LinBiao ChengHongjiang LiuZhiqiang Yu . Luminescence-activated Pt(Ⅳ) prodrug for in situ triggerable cancer therapy. Chinese Chemical Letters, 2024, 35(7): 109134-. doi: 10.1016/j.cclet.2023.109134

    9. [9]

      Hai-Yang SongJun JiangYu-Hang SongMin-Hang ZhouChao WuXiang ChenWei-Min He . Supporting-electrolyte-free electrochemical [2 + 2 + 1] annulation of benzo[d]isothiazole 1,1-dioxides, N-arylglycines and paraformaldehyde. Chinese Chemical Letters, 2024, 35(6): 109246-. doi: 10.1016/j.cclet.2023.109246

    10. [10]

      Ze-Yuan MaMei XiaoCheng-Kun LiAdedamola ShoberuJian-Ping ZouS-(1,3-Dioxoisoindolin-2-yl)O,O-diethyl phosphorothioate (SDDP): A practical electrophilic reagent for the phosphorothiolation of electron-rich compounds. Chinese Chemical Letters, 2024, 35(5): 109076-. doi: 10.1016/j.cclet.2023.109076

    11. [11]

      Zhirong YangShan WangMing JiangGengchen LiLong LiFangzhi PengZhihui Shao . One stone three birds: Ni-catalyzed asymmetric allenylic substitution of allenic ethers, hydroalkylation of 1,3-enynes and double alkylation of enynyl ethers. Chinese Chemical Letters, 2024, 35(8): 109518-. doi: 10.1016/j.cclet.2024.109518

    12. [12]

      Yinwu Su Xuanwen Zheng Jianghui Du Boda Li Tao Wang Zhiyan Huang . Green Synthesis of 1,3-Dibromoacetone Using Halogen Exchange Method: Recommending a Basic Organic Synthesis Teaching Experiment. University Chemistry, 2024, 39(5): 307-314. doi: 10.3866/PKU.DXHX202311092

    13. [13]

      Zhuoming Liang Ming Chen Zhiwen Zheng Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By 1H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029

    14. [14]

      Peng WangJianjun WangNi SongXin ZhouMing Li . Radical dehydroxymethylative fluorination of aliphatic primary alcohols and diverse functionalization of α-fluoroimides via BF3·OEt2-catalyzed C‒F bond activation. Chinese Chemical Letters, 2025, 36(1): 109748-. doi: 10.1016/j.cclet.2024.109748

    15. [15]

      Yan ZhuJia LiuMeiheng LvTingting WangDongxiang ZhangRong ShangXin-Dong JiangJianjun DuGuiling Wang . Heavy-atom-free orthogonal configurative dye 1,7-di-anthra-aza-BODIPY for singlet oxygen generation. Chinese Chemical Letters, 2024, 35(10): 109446-. doi: 10.1016/j.cclet.2023.109446

    16. [16]

      Hui-Juan WangWen-Wen XingZhen-Hai YuYong-Xue LiHeng-Yi ZhangQilin YuHongjie ZhuYao-Yao WangYu Liu . Cucurbit[7]uril confined phenothiazine bridged bis(bromophenyl pyridine) activated NIR luminescence for lysosome imaging. Chinese Chemical Letters, 2024, 35(6): 109183-. doi: 10.1016/j.cclet.2023.109183

    17. [17]

      Zhixue LiuHaiqi ChenLijuan GuoXinyao SunZhi-Yuan ZhangJunyi ChenMing DongChunju Li . Luminescent terphen[3]arene sulfate-activated FRET assemblies for cell imaging. Chinese Chemical Letters, 2024, 35(9): 109666-. doi: 10.1016/j.cclet.2024.109666

    18. [18]

      Zheng Zhao Ben Zhong Tang . An efficient strategy enabling solution processable thermally activated delayed fluorescence emitter with high horizontal dipole orientation. Chinese Journal of Structural Chemistry, 2024, 43(6): 100270-100270. doi: 10.1016/j.cjsc.2024.100270

    19. [19]

      Qiongqiong WanYanan XiaoGuifang FengXin DongWenjing NieMing GaoQingtao MengSuming Chen . Visible-light-activated aziridination reaction enables simultaneous resolving of C=C bond location and the sn-position isomers in lipids. Chinese Chemical Letters, 2024, 35(4): 108775-. doi: 10.1016/j.cclet.2023.108775

    20. [20]

      Yuan ZhangShenghao GongA.R. Mahammed ShaheerRong CaoTianfu Liu . Plasmon-enhanced photocatalytic oxidative coupling of amines in the air using a delicate Ag nanowire@NH2-UiO-66 core-shell nanostructures. Chinese Chemical Letters, 2024, 35(4): 108587-. doi: 10.1016/j.cclet.2023.108587

Metrics
  • PDF Downloads(0)
  • Abstract views(649)
  • HTML views(14)

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