An approach to the Paal-Knorr pyrroles synthesis catalyzed by Sc(OTf)3 under solvent-free conditions

被引:208
作者
Chen, Jiuxi
Wu, Huayue
Zheng, Zhiguo
Jin, Can
Zhang, Xingxian
Su, Weike [1 ]
机构
[1] Wenzhou Univ, Coll Chem & Mat Sci, Wenzhou 325027, Peoples R China
[2] Zhejiang Univ Technol, Coll Pharmaceut Sci, Zhejiang Key Lab Pharmaceut Engn, Hangzhou 310014, Peoples R China
[3] Zhejiang Hisoar Pharmaceut Co Ltd, Taizhou 318000, Peoples R China
基金
中国国家自然科学基金;
关键词
scandium triflate; pyrrole; Paal-Knorr; solvent-free conditions;
D O I
10.1016/j.tetlet.2006.05.085
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile synthesis of N-substituted pyrroles by the Paal-Knorr condensation has been accomplished using a simple procedure. Among different metal triflates screened, 1 mol % Sc(OT)(3) efficiently promoted the reaction to give excellent yield (89-98%) under mild reaction conditions. Additionally, Sc(OTf)(3) could be recovered easily after the reactions and reused without evident loss in activity. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5383 / 5387
页数:5
相关论文
共 60 条
  • [1] Versatility of Weinreb amides in the Knorr pyrrole synthesis
    Alberola, A
    Ortega, AG
    Sádaba, ML
    Sañudo, C
    [J]. TETRAHEDRON, 1999, 55 (21) : 6555 - 6566
  • [2] Antitumor imidazotetrazines. 41. Conjugation of the antitumor agents mitozolomide and temozolomide to peptides and lexitropsins bearing DNA major and minor groove-binding structural motifs
    Arrowsmith, J
    Jennings, SA
    Clark, AS
    Stevens, MFG
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (25) : 5458 - 5470
  • [3] Ballini R, 2000, SYNLETT, P391
  • [4] Pyrrole syntheses by multicomponent coupling reactions
    Balme, G
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (46) : 6238 - 6241
  • [5] Straightforward highly efficient Paal-Knorr synthesis of pyrroles
    Banik, BK
    Banik, I
    Renteria, M
    Dasgupta, SK
    [J]. TETRAHEDRON LETTERS, 2005, 46 (15) : 2643 - 2645
  • [6] Simple synthesis of substituted pyrroles
    Banik, BK
    Samajdar, S
    Banik, I
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (01) : 213 - 216
  • [7] A new method for the synthesis of plurisubstituted pyrroles
    Bashiardes, G
    Safir, I
    Barbot, F
    Laduranty, J
    [J]. TETRAHEDRON LETTERS, 2003, 44 (46) : 8417 - 8420
  • [8] Catalytic multicomponent synthesis of highly substituted pyrroles utilizing a one-pot Sila-Stetter/Paal-Knorr strategy
    Bharadwaj, AR
    Scheidt, KA
    [J]. ORGANIC LETTERS, 2004, 6 (14) : 2465 - 2468
  • [9] A novel one-pot pyrrole synthesis via a coupling-isomerization-Stetter-Paal-knorr sequence
    Braun, RU
    Zeitler, K
    Muller, TJJ
    [J]. ORGANIC LETTERS, 2001, 3 (21) : 3297 - 3300
  • [10] NOVEL SYNTHESIS OF 3H-PYRROLES, AND NOVEL INTERMEDIATES IN THE PAAL-KNORR 1H-PYRROLE SYNTHESIS - 2-HYDROXY-3,4-DIHYDRO-2H-PYRROLES FROM 1,4-DIKETONES AND LIQUID-AMMONIA
    CHIU, PK
    LUI, KH
    MAINI, PN
    SAMMES, MP
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (02) : 109 - 110