Synthesis of 2,3,4-trisubstituted pyrrole derivatives via [3+2] cyclization of activated methylene isocyanides with 4-(arylidene)-2-substituted oxazol-5(4H)-ones

被引：9
作者：
Zhang, Jing [1 ,2 ]
Liu, Man [2 ]
Li, Chao [2 ]
Xu, Yan-Jun [1 ]
Dong, Lin [2 ]
机构：
[1] Sichuan Normal Univ, Coll Chem & Mat Sci, Chengdu 610066, Sichuan, Peoples R China
[2] Sichuan Univ, West China Sch Pharm, Educ Minist, Key Lab Drug Targeting & Drug Delivery Syst, Chengdu 610041, Peoples R China
来源：
ORGANIC CHEMISTRY FRONTIERS | 2020年 / 7卷 / 02期
关键词：
ALPHA-ACIDIC ISOCYANIDES; REGIOSELECTIVE SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; POLYSUBSTITUTED PYRROLES; SUBSTITUTED PYRROLES; CONGOCIDINE; ISOCYANOACETATES; ANNULATION; ALKYNES; YLIDES;
D O I：
10.1039/c9qo01044k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An efficient base-catalyzed [3 + 2] cyclization between isocyanides and 4-(arylidene)-2-substituted oxazol-5(4H)-ones has been successfully developed to form 2,3,4-trisubstituted and 2,2,3,4-tetrasubstituted pyrrole derivatives. This transition metal free reaction occurs at room temperature under environmentally friendly conditions, tolerating water and air.
引用
收藏
页码：420 / 424
页数：5
相关论文
共 50 条
  • [41] Regio- and diastereoselective synthesis of N-substituted 2-acyl-3-aryl-3,5-dihydrofuro[3,2-c]pyridin-4(2H)-ones
    Kvetkin, Evgeny A.
    Osipov, Dmitry, V
    Krasnikov, Pavel E.
    Osyanin, Vitaly A.
    Klimochkin, Yuri N.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2020, 56 (11) : 1423 - 1428
  • [42] Cyclization Reaction of 2-Azido-1-(2-hydroxyphenyl)ethanones with Terminal Alkynoates Catalyzed by 4-Dimethylaminopyridine (DMAP): Synthesis of 2-Aminobenzofuran-3(2H)-one Derivatives
    Meng, Ling-Guo
    Ge, Ni-Lin
    Yang, Ming-Ming
    Wang, Lei
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 2011 (19) : 3403 - 3406
  • [43] Simple synthesis of 2-[5-substituted-4-(trichloroacetyl)-1H-pyrazole-3-carbonyloxy]benzoic acids
    Lisovenko, N. Yu.
    Nasibullina, E. R.
    Dmitriev, M. V.
    RUSSIAN CHEMICAL BULLETIN, 2019, 68 (03) : 578 - 582
  • [44] Copper-catalyzed one-pot synthesis of 2H-1,4-benzoxazin-3-(4H)-ones from 2-(o-haloaryloxy) acyl chlorides and primary amines
    Hu, Qunxian
    Xia, Ziming
    Fan, Ling
    Zheng, Jiening
    Wang, Xiaoxia
    Lv, Xin
    ARKIVOC, 2012, : 129 - 142
  • [45] Chemoselective Synthesis of 1-Substituted 4-Amino-2-(trifluoromethyl)-1H-pyrroles through the Heterocyclization Reaction of 4-Methoxy-5-bromo-1,1,1-trifluoropent-3-en-2-ones with Amines
    Aquino, Estefania da C.
    Leonel, Guilherme
    Gariboti, Vanessa C.
    Frizzo, Clarissa P.
    Martins, Marcos A. P.
    Bonacorso, Helio G.
    Zanatta, Nilo
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (24) : 12453 - 12459
  • [46] Click chemistry based regioselective one-pot synthesis of coumarin-3-yl-methyl-1,2,3-triazolyl-1,2,4-triazol-3(4H)-ones as newer potent antitubercular agents
    Somagond, Shilpa M.
    Kamble, Ravindra R.
    Bayannavar, Praveen K.
    Shaikh, Saba Kauser J.
    Joshi, Shrinivas D.
    Kumbar, Vijay M.
    Nesaragi, Aravind R.
    Kariduraganavar, Mahadevappa Y.
    ARCHIV DER PHARMAZIE, 2019, 352 (10)
  • [47] Regioselective Synthesis of 3-Substituted Isocoumarin-1-imines via Palladium-Catalyzed Denitrogenative Transannulation of 1,2,3-Benzotriazin-4(3H)-ones and Terminal Alkynes
    Balakrishnan, Madasamy Hari
    Sureshbabu, Popuri
    Korivi, Ramaraju
    Mannathan, Subramaniyan
    CHEMISTRY-AN ASIAN JOURNAL, 2023, 18 (21)
  • [48] SYNTHESIS AND CHARACTERIZATION OF NEW 3 ",5"-DIARYL-3"H-DISPIROPYRAN/THIOPYRAN[4,2′CHROMAN-3′,2"-[1,3,4-THIADIAZOL]-4′-ONE DERIVATIVES AND RELATED COMPOUNDS AS ANTICANCER AND ANTIVIRAL AGENTS
    Hegab, Mohamed I.
    Morsy, Eman. M. H.
    Abd El-Megeid, Ahmed E.
    Ali, Mamdouh M.
    El-Senousy, W. M.
    Tolan, Hala E. M.
    Gad, Farouk A.
    Abdel-Megeid, Farouk M. E.
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2015, 190 (11) : 1901 - 1911
  • [49] Synthesis, photophysical, solvatochromic and DFT studies of (Z)-2-(2-Phenyl-4H-benzo[4,5]thiazolo[3,2-a]pyrimidin-4-ylidene)acetonitrile derivatives
    Patil, Raosaheb S.
    Patil, Atul S.
    Patil, Vikas S.
    Jirimali, Harishchandra D.
    Mahulikar, Pramod P.
    JOURNAL OF LUMINESCENCE, 2019, 210 : 303 - 310
  • [50] Synthesis of Pyrrolo[3,2-d] pyrimidin-4-ones via Cascade Alkyne-isocyanide [3+2] Cycloaddition/Boulton-Katritzky Rearrangement/Ring Expansion Process
    Luo Jianghao
    Ma Haowen
    Zhang Jiehao
    Zhou Wei
    Cai Qian
    ACTA CHIMICA SINICA, 2023, 81 (08) : 898 - 904
12345