The rapid preparation of 2-aminosulfonamide-1,3,4-oxadiazoles using polymer-supported reagents and microwave heating

被引：115
作者：
Baxendale, IR
Ley, SV
Martinelli, M
机构：
[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
[2] NiKem Res Srl, Milan, Italy
来源：
TETRAHEDRON | 2005年 / 61卷 / 22期
基金：
英国工程与自然科学研究理事会;
关键词：
polymer-supported reagents; oxaziazole; thiadiazole; combinatorial chemistry; microwave;
D O I：
10.1016/j.tet.2005.03.062
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Herein, we report on the preparation of a library of 5-substituted-2-amino-1,3,4-oxadiazoles and the corresponding thiadiazole analogues. Presented is a one-pot preparation of the 2-ammosulfonylated analogues through a three component coupling of an acylhydrazine, an isocyanate and sulfonyl chloride promoted by a polymer-supported phosphazine base under microwave dielectric heating. Also described is the optimization process and details pertaining to the elucidation of the reaction products. (c) 2005 Elsevier Ltd. All rights reserved.
引用
收藏
页码：5323 / 5349
页数：27
相关论文
共 92 条
  • [21] Synthesis of an array of potential matrix metalloproteinase inhibitors using a sequence of polymer-supported reagents
    Caldarelli, M
    Habermann, J
    Ley, SV
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1999, 9 (14) : 2049 - 2052
  • [22] Clean and efficient synthesis of azo dyes using polymer-supported reagents
    Caldarelli, M
    Baxendale, IR
    Ley, SV
    [J]. GREEN CHEMISTRY, 2000, 2 (02) : 43 - 45
  • [23] Clean five-step synthesis of an array of 1,2,3,4-tetra-substituted pyrroles using polymer-supported reagents
    Caldarelli, M
    Habermann, J
    Ley, SV
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (02): : 107 - 110
  • [24] Cesur N., 2002, PHARM TURCICA, V44, P23
  • [25] Enzyme catalysed oxidation of nazlinin and nazlinin derivatives. Characterisation of the reaction products.
    Cheng, E
    Botzem, J
    Wanner, MJ
    Burm, BEA
    Koomen, GJ
    [J]. TETRAHEDRON, 1996, 52 (19) : 6725 - 6732
  • [26] Efficient one-pot preparation of 5-substituted-2-amino-1,3,4-oxadiazoles using resin-bound reagents
    Coppo, FT
    Evans, KA
    Graybill, TL
    Burton, G
    [J]. TETRAHEDRON LETTERS, 2004, 45 (16) : 3257 - 3260
  • [27] A new synthesis of 1,2,4-triazolin-5-ones:: application to the convergent synthesis of an NK1 antagonist
    Cowden, CJ
    Wilson, RD
    Bishop, BC
    Cottrell, IF
    Davies, AJ
    Dolling, UH
    [J]. TETRAHEDRON LETTERS, 2000, 41 (44) : 8661 - 8664
  • [28] TOTAL SYNTHESIS OF 2'-DEOXYCADEGUOMYCIN, A NEW PYRROLO[2,3-D]PYRIMIDINE NUCLEOTIDE ANALOG
    EDSTROM, ED
    WEI, Y
    [J]. TETRAHEDRON LETTERS, 1994, 35 (48) : 8989 - 8990
  • [29] Development of methylthiomethyl (MTM) protection for N-1 of pyrrolo[2,3-d]pyrimidin-2,4-diones
    Edstrom, ED
    Feng, XQ
    Tumkevicius, S
    [J]. TETRAHEDRON LETTERS, 1996, 37 (06) : 759 - 762
  • [30] Synthesis and spectral characterization of novel 1,3,4-oxadiazole and 1,2,4-triazole derivatives: Synthesis for potential pharmacological activities
    Faidallah, HM
    Sharshira, EM
    Basaif, SA
    A-Ba-Oum, AEK
    [J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2002, 177 (01) : 67 - 79
12345678910