Novel One-Pot Cyclization of the Blaise Reaction Intermediate and Arylglyoxals: The Synthesis of Substituted NH -Pyrroles

被引：12
作者：
Chen, Zhiwei [1 ,2 ]
Chen, Hao [1 ,2 ]
Yang, Xiaofeng [1 ,2 ]
Chang, Xiangqing [1 ,2 ]
机构：
[1] Zhejiang Univ Technol, Collaborat Innovat Ctr Yangtze River Delta Reg Gr, Natl Engn Res Ctr Proc Dev Act Pharmaceut Ingredi, Hangzhou 310014, Zhejiang, Peoples R China
[2] Zhejiang Univ Technol, Coll Pharmaceut Sci, Key Lab Green Pharmaceut Technol & Related Equipm, Minist Educ, Hangzhou 310014, Zhejiang, Peoples R China
来源：
SYNLETT | 2017年 / 28卷 / 12期
基金：
中国国家自然科学基金;
关键词：
pyrroles; Blaise reaction intermediate; arylglyoxals; Reformatsky reagent; chromeno; 4-hydroxy-1; H; -pyrrole; POLYSUBSTITUTED PYRROLES; FUNCTIONALIZED PYRROLES; 3-COMPONENT SYNTHESIS; DERIVATIVES; NITRILES; AMINES; CYCLOADDITION; ROSEOPHILIN; ALKALOIDS; ETHERS;
D O I：
10.1055/s-0036-1588168
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel tandem Blaise reaction for the one-pot synthesis of substituted NH-pyrroles was described. The Blaise reaction intermediate, generated in situ from Reformatsky reagent and nitrile, reacted with arylglyoxals chemoselectively to afford a wide variety of substituted NH-pyrroles in good yields.
引用
收藏
页码：1463 / 1466
页数：4
相关论文
共 50 条
  • [41] An Unexpected Diastereoselective Synthesis of Novel Substituted Pyridines via One-Pot, Four-Component Reaction
    Zangouei, Mahdieh
    Esmaeili, Abbas Ali
    Mague, Joel T.
    SYNLETT, 2016, 27 (11) : 1669 - 1673
  • [42] One-pot facile synthesis of polysubstituted pyridines via tandem reaction of the Blaise reaction intermediates and 3-formylchromones
    Chen, Zhiwei
    Dai, Zhaoran
    Zhu, Zhangxia
    Yang, XiaoFeng
    TETRAHEDRON LETTERS, 2017, 58 (13) : 1258 - 1261
  • [43] One-pot synthesis of coumarin substituted dihydrofurans
    Chunduru, Venkata Sreenivasa Rao
    Vedula, Rajeswar Rao
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 2012, 51 (09): : 1417 - 1420
  • [44] Efficient synthesis of pentasubstituted pyrroles via one-pot reactions of arylamines, acetylenedicarboxylates, and 3-phenacylideneoxindoles
    Han, Ying
    Sun, Yan
    Sun, Jing
    Yan, Chao-Guo
    TETRAHEDRON, 2012, 68 (39) : 8256 - 8260
  • [45] An efficient one-pot synthesis of tri-substituted thiophenes via a multicomponent reaction in water
    Moghaddam, Firouz Matloubi
    Bardajee, Ghasem Rezanejade
    Dolabi, Maliheh
    JOURNAL OF SULFUR CHEMISTRY, 2010, 31 (05) : 387 - 393
  • [46] β-Cyclodextrin as a recyclable catalyst: aqueous phase one-pot four-component synthesis of polyfunctionalized pyrroles
    Konkala, Karnakar
    Chowrasia, Rakhi
    Manjari, Padma S.
    Domingues, Nelson L. C.
    Katla, Ramesh
    RSC ADVANCES, 2016, 6 (49) : 43339 - 43344
  • [47] Modular Three-Component Organocatalytic Synthesis of 3,4-Disubstituted Pyrroles by a One-Pot Domino Reaction
    Martin-Santos, Cecilia
    Jarava-Barrera, Carlos
    Parra, Alejandro
    Esteban, Francisco
    Navarro-Ranninger, Carmen
    Aleman, Jose
    CHEMCATCHEM, 2012, 4 (07) : 976 - 979
  • [48] THREE-COMPONENT REACTION OF TRIPHENYLPHOSPHINE, DIALKYL ACETYLENEDICARBOXYLATE, AND 2-AMINOTHIAZOLE OR 2-AMINOBENZOTHIAZOLE IN THE PRESENCE OF ARYLGLYOXALS: AN EFFICIENT ONE-POT SYNTHESIS OF HIGHLY FUNCTIONALIZED PYRROLES
    Anary-Abbasinejad, Mohammad
    Farashah, Hamidreza Dehghanpour
    Hassanabadi, Alireza
    Anaraki-Ardakani, Hossein
    Shams, Nasim
    SYNTHETIC COMMUNICATIONS, 2012, 42 (13) : 1877 - 1884
  • [49] Production of polysubstituted pyrroles from lignin β-O-4 models via a one-pot multicomponent reaction
    Qiang, Qian
    Ding, Yangming
    Luo, Qi
    Guo, Tenglong
    Qu, Boquan
    Tian, Shenglong
    Yang, Huamei
    Liu, Yanfang
    Li, Changzhi
    Zhang, Tao
    INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES, 2025, 308
  • [50] One-pot synthesis of new highly substituted allylic phosphorodiamidates
    Bahri, Leila
    Barhoumi-Slimi, T.
    Mallek, R.
    Sanhoury, M. A. K.
    Crousse, B.
    Ben Dhia, M. T.
    JOURNAL OF FLUORINE CHEMISTRY, 2016, 189 : 96 - 101
12345