The Bohlmann-Rahtz route to functionalised pyridine scaffolds and their use in library synthesis

被引:44
作者
Bashford, KE
Burton, MB
Cameron, S
Cooper, AL
Hogg, RD
Kane, PD
MacManus, DA
Matrunola, CA
Moody, CJ
Robertson, AAB
Warne, MR
机构
[1] Tripos Receptor Res Ltd, Bude EX23 8LY, Cornwall, England
[2] Univ Exeter, Sch Chem, Exeter EX4 4QD, Devon, England
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1016/S0040-4039(03)00034-0
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Bohlmann-Rahtz reaction has been used to prepare 2,3,6-trisubstituted pyridines suitable for use in library synthesis. The synthesis of piperidine substituted nicotinic acid derivative 9 has been optimised and carried out on a large scale to give ca. 500 g of scaffold which was used in the generation of the pyridine library 11. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:1627 / 1629
页数:3
相关论文
共 22 条
  • [1] The synthesis of novel heterocyclic substituted α-amino acids;: further exploitation of α-amino acid alkynyl ketones as reactive substrates
    Adlington, RM
    Baldwin, JE
    Catterick, D
    Pritchard, GJ
    Tang, LT
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (15): : 2311 - 2316
  • [2] The synthesis of novel heterocyclic substituted α-amino acids;: further exploitation of α-amino acid alkynyl ketones
    Adlington, RM
    Baldwin, JE
    Catterick, D
    Pritchard, GJ
    Tang, LT
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (03): : 303 - 305
  • [3] A facile solution phase combinatorial synthesis of tetrasubstituted pyridines using the Bohlmann-Rahtz heteroannulation reaction
    Bagley, MC
    Dale, JW
    Ohnesorge, M
    Xiong, X
    Bower, J
    [J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2003, 5 (01): : 41 - 44
  • [4] A new one-step synthesis of pyridines under microwave-assisted conditions
    Bagley, MC
    Lunn, R
    Xiong, X
    [J]. TETRAHEDRON LETTERS, 2002, 43 (46) : 8331 - 8334
  • [5] A new one-pot three-component condensation reaction for the synthesis of 2,3,4,6-tetrasubstituted pyridines
    Bagley, MC
    Dale, JW
    Bower, J
    [J]. CHEMICAL COMMUNICATIONS, 2002, (16) : 1682 - 1683
  • [6] Synthesis of tetrasubstituted pyridines by the acid-catalysed Bohlmann-Rahtz reaction
    Bagley, MC
    Brace, C
    Dale, JW
    Ohnesorge, M
    Phillips, NG
    Xiong, X
    Bower, J
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (14): : 1663 - 1671
  • [7] Bagley MC, 2001, SYNLETT, P1523
  • [8] Bagley MC, 2001, SYNLETT, P1149
  • [9] Total synthesis of the thiopeptide promothiocin A
    Bagley, MC
    Bashford, KE
    Hesketh, CL
    Moody, CJ
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2000, 122 (14) : 3301 - 3313
  • [10] UBER EINE NEUE PYRIDINSYNTHESE
    BOHLMANN, F
    RAHTZ, D
    [J]. CHEMISCHE BERICHTE-RECUEIL, 1957, 90 (10): : 2265 - 2272