A versatile approach to 3-alkyl and 2,3-dialkylpyrroles

被引：3
|
作者：
Burley, I
Bilic, B
Hewson, AT
Newton, JRA
机构：
[1] Sheffield Hallam Univ, Div Chem, Sheffield S1 1WB, S Yorkshire, England
[2] Sheffield Hallam Univ, Biomed Res Ctr, Sheffield S1 1WB, S Yorkshire, England
来源：
TETRAHEDRON LETTERS | 2000年 / 41卷 / 46期
基金：
英国工程与自然科学研究理事会;
关键词：
pyrrolines; aromatisation; pyrroles; intramolecular Wittig;
D O I：
10.1016/S0040-4039(00)01591-4
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A route is described towards N-benzoyl-3-alkyl and N-benzoyl-2,3-dialkyl pyrroles from alpha -amido-ketones via an intramolecular Wittig reaction to afford 4-phenylthio-3-pyrrolines which are then oxidised to the corresponding sulphones and aromatised by treatment with potassium t-butoxide. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：8969 / 8972
页数：4
相关论文
共 49 条
  • [31] Preparation of 3-Diazoindolin-2-imines via Cascade Reaction between Indoles and Sulfonylazides and Their Extensions to 2,3-Diaminoindoles and Imidazo[4,5-b]indoles
    Sheng, Guorong
    Huang, Kai
    Chi, Zhihao
    Ding, Hualong
    Xing, Yanpeng
    Lu, Ping
    Wang, Yanguang
    ORGANIC LETTERS, 2014, 16 (19) : 5096 - 5099
  • [32] One-Pot Synthesis and Intramolecular Cyclization of 5-(Prop-2-ynylsulfanyl)-1H-pyrrol-2-amines: A Simple Approach to 2,7-Dihydrothiopyrano[2,3-b]pyrrol-6-amines
    Nedolya, Nina A.
    Tarasova, Ol'ga A.
    Albanov, Alexander I.
    Trofimov, Boris A.
    SYNTHESIS-STUTTGART, 2016, 48 (23): : 4278 - 4294
  • [33] Copper-catalyzed [3+2] annulation of propargylic acetates with anilines in the presence of trimethylsilyl chloride leading to 2,3-disubstituted indoles via an aza-Claisen rearrangement
    Sakai, Norio
    Enomoto, Kota
    Takayanagi, Mitsumasa
    Konakahara, Takeo
    Ogiwara, Yohei
    TETRAHEDRON LETTERS, 2016, 57 (20) : 2175 - 2178
  • [34] Mass spectra of new heterocycles: XIV. Investigation of 2-(alkyl- and propargylsulfanyl)-3-(ferrocenylmethoxy)pyrroles by electron ionization and laser desorption/ionization
    Klyba, L. V.
    Tarasova, O. A.
    Nedolya, N. A.
    Sanzheeva, E. R.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 52 (11) : 1587 - 1592
  • [35] The Organocatalytic Approach to Enantiopure 2H- and 3H-Pyrroles: Inhibitors of the Hedgehog Signaling Pathway
    Koetzner, Lisa
    Leutzsch, Markus
    Sievers, Sonja
    Patil, Sumersing
    Waldmann, Herbert
    Zheng, Yiying
    Thiel, Walter
    List, Benjamin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (27) : 7693 - 7697
  • [36] [3+3]-Annulation of Cyclic Nitronates with Vinyl Diazoacetates: Diastereoselective Synthesis of Partially Saturated [1,2]Oxazino[2,3-b][1,2]oxazines and Their Base-Promoted Ring Contraction to Pyrrolo[1,2-b][1,2]oxazine Derivatives
    Antonova, Yulia A.
    Nelyubina, Yulia V.
    Ioffe, Sema L.
    Tabolin, Andrey A.
    MOLECULES, 2023, 28 (07):
  • [37] Versatile synthesis of pyrrole-2-acetic esters and (pyridine-2-one)-3-acetic amides by palladium-catalyzed, carbon dioxide-promoted oxidative carbonylation of (Z)-(2-en-4-ynyl)amines
    Gabriele, Bartolo
    Salerno, Giuseppe
    Fazio, Alessia
    Veltri, Lucia
    ADVANCED SYNTHESIS & CATALYSIS, 2006, 348 (15) : 2212 - 2222
  • [38] Contributing to Biochemistry and Optoelectronics: Pyrrolo[1',2':2,3]imidazo[1,5-a]indoles and Cyclohepta[4,5]pyrrolo[1,2-c]pyrrolo[1,2-a]imidazoles via [3+2] Annulation of Acylethynylcycloalka[b]pyrroles with ?1-Pyrrolines
    Oparina, Ludmila A.
    Kolyvanov, Nikita A.
    Ushakov, Igor A.
    Nikitina, Lina P.
    Petrova, Olga V.
    Sobenina, Lyubov N.
    Petrushenko, Konstantin B.
    Trofimov, Boris A.
    INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2023, 24 (04)
  • [39] Mass spectra of new heterocycles: X. Fragmentation of the molecular ions of 1-alkyl(cycloalkyl, aryl)-3-alkoxy(aryl)-2-methylsulfanyl-1H-pyrroles
    Klyba, L. V.
    Nedolya, N. A.
    Tarasova, O. A.
    Zhanchipova, E. R.
    Volostnykh, O. G.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 46 (07) : 1038 - 1048
  • [40] Regioselective C2-lithiation of N-Boc-3-bromopyrroles: a novel approach towards the synthesis and scale-up of 3-(2-formyl-4-methyl-1-H-pyrrol-3-yl)propanoic acid
    Dai, Donghua
    Venepalli, Bhaskar Rao
    TETRAHEDRON LETTERS, 2015, 56 (19) : 2402 - 2405
12345