Synthesis of 3-halo-2,5-disubstituted furans via CuX mediated cyclization-halogenation reactions

被引：4
|
作者：
Yazici, Arife [1 ]
Pyne, Stephen G. [1 ]
机构：
[1] Univ Wollongong, Sch Chem, Wollongong, NSW 2522, Australia
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 12期
基金：
澳大利亚研究理事会;
关键词：
Cyclization-halogenation; Cyclization-cyanation; Cu(I) salts; 2,3,5-Trisubstituted furans;
D O I：
10.1016/j.tetlet.2011.01.120
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The Cu(I) halide (X = I, Br, Cl) mediated reactions of Cbz-protected cis-2-phenylethenyl-3-hydroxypyrrolidine gave novel 3-halo-2,5-trisubstituted furans in good yields, via a cyclization-halogenation, ring-opening reaction sequence. In contrast, the reactions with CuCN gave mainly the corresponding 3-cyanofuro[3,2-b]pyrrole formed from a cyclization-cyanation reaction. (C) 2011 Published by Elsevier Ltd.
引用
收藏
页码：1398 / 1400
页数：3
相关论文
共 50 条
  • [21] Synthesis of 2,5-Disubstituted Furans from Sc(OTf)3 Catalyzed Reaction of Aryl Oxiranediesters with γ-Hydroxyenones
    Mondal, Keshab
    Pan, Subhas Chandra
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (08): : 4415 - 4421
  • [22] Anodic Cyclization: A Protocol for the Green Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles
    Singh, S.
    Sharma, L. K.
    Saraswat, A.
    Srivastava, M. K.
    Siddiqui, I. R.
    Singh, R. K. P.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2014, 49 (10) : 1508 - 1514
  • [23] Anodic Cyclization: A Protocol for the Green Synthesis of 2,5-Disubstituted 1,3,4-Oxadiazoles
    S. Singh
    L. K. Sharma
    A. Saraswat
    M. K. Srivastava
    I. R. Siddiqui
    R. K. P. Singh
    Chemistry of Heterocyclic Compounds, 2014, 49 : 1508 - 1514
  • [24] Synthesis of 2,5-Disubstituted 3-(Phenylsulfonyl)pyrrolidines via 5-Endo-Trig Cyclisation Reactions
    Synlett, 12 (1423):
  • [25] Synthesis of 2,5-disubstituted 3-(phenylsulfonyl)pyrrolidines via 5-endo-trig cyclisation reactions
    Craig, D
    Jones, PS
    Rowlands, GJ
    SYNLETT, 1997, (12) : 1423 - 1425
  • [26] Efficient synthesis of 2-mono- and 2,5-disubstituted furans via the CuI-catalyzed cycloisomerization of alkynyl ketones
    Kel'in, AV
    Gevorgyan, V
    JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (01): : 95 - 98
  • [27] Synthesis of 2,5-disubstituted pyrroles and pyrrolidines by intramolecular cyclization of 6-amino-3-keto sulfones
    Benetti, Simonetta
    De Risi, Carmela
    Marchetti, Paolo
    Pollini, Gian P.
    Zanirato, Vinicio
    Synthesis, 2002, (03) : 331 - 338
  • [28] Synthesis of 2,5-disubstituted pyrroles and pyrrolidines by intramolecular cyclization of 6-amino-3-keto sulfones
    Benetti, S
    De Risi, C
    Marchetti, P
    Pollini, GP
    Zanirato, V
    SYNTHESIS-STUTTGART, 2002, (03): : 331 - 338
  • [29] A novel synthesis of 2,5-disubstituted 1,3,4-oxadiazolines by the regioselective cyclization of 1,4-disubstituted thiosemicarbazides
    Feng, Dexin
    Huang, You
    Chen, Ruyu
    Yu, Yaqin
    Song, Haibin
    SYNTHESIS-STUTTGART, 2007, 12 (12): : 1779 - 1784
  • [30] Synthesis of 2,5-disubstituted 1,3,4-oxadiazoles by visible-light-mediated decarboxylation-cyclization of hydrazides and diketones
    Diao, Pinhui
    Ge, Yanqin
    Zhang, Wenpei
    Xu, Chen
    Zhang, Nannan
    Guo, Cheng
    TETRAHEDRON LETTERS, 2018, 59 (08) : 767 - 770
12345