An Approach to 2,4-Substituted Pyrazolo[1,5-a]pyridines and Pyrazolo[1,5-a]azepines by Ring-Closing Metathesis

被引:13
作者
Fustero, Santos [1 ,2 ]
Roman, Raquel [1 ]
Asensio, Amparo [1 ]
Maestro, Miguel A. [3 ]
Acena, Jose L. [4 ]
Simon-Fuentes, Antonio [1 ]
机构
[1] Univ Valencia, Dept Quim Organ, E-46100 Valencia, Spain
[2] Ctr Invest Principe Felipe, Lab Mol Organ, Valencia 46012, Spain
[3] Univ A Coruna, Dept Quim Fundamental, La Coruna 15071, Spain
[4] Univ Basque Country, Dept Organ Chem 1, San Sebastian 20018, Spain
关键词
Synthetic methods; Asymmetric synthesis; Metathesis; Peptidomimetics; Nitrogen heterocycles; TERT-BUTANESULFINYL IMINES; FUSED BICYCLIC IMIDAZOLES; ASYMMETRIC-SYNTHESIS; ORGANOMETALLIC REAGENTS; MEDIATED ALLYLATION; RECEPTOR; DERIVATIVES; DISCOVERY; AMINES; ANTIHERPETICS;
D O I
10.1002/ejoc.201300901
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The ring-closing metathesis (RCM) reactions of dienylpyrazoles have been employed in the synthesis of pyrazolo[1,5-a]pyridine and pyrazolo[1,5-a]azepine derivatives. Based on this approach, the diastereoselective synthesis of potential peptidomimetics containing four amino acid residues with the second (i+1) and third (i+2) fragments having been substituted by bicyclic frameworks is described.
引用
收藏
页码:7164 / 7174
页数:11
相关论文
共 55 条
  • [1] Aboul-Fadl T, 2000, SYNTHESIS-STUTTGART, P1727
  • [2] Discovery of FK453, a novel non-xanthine adenosine A(1) receptor antagonist
    Akahane, A
    Katayama, H
    Mitsunaga, T
    Kita, Y
    Kusunoki, T
    Terai, T
    Yoshida, K
    Shiokawa, Y
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (17) : 2059 - 2062
  • [3] Discovery of 6-oxo-3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)-1(6H)pyridazinebutanoic acid (FK838):: A novel non-xanthine adenosine A1 receptor antagonist with potent diuretic activity
    Akahane, A
    Katayama, H
    Mitsunaga, T
    Kato, T
    Kinoshita, T
    Kita, Y
    Kusunoki, T
    Terai, T
    Yoshida, K
    Shiokawa, Y
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1999, 42 (05) : 779 - 783
  • [4] Synthesis of C-6 substituted pyrazolol[1,5-α]pyridines with potent activity against herpesviruses
    Allen, SH
    Johns, BA
    Gudmundsson, KS
    Freeman, GA
    Boyd, FL
    Sexton, CH
    Selleseth, DW
    Creech, KL
    Moniri, KR
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (04) : 944 - 954
  • [5] Triorganozincates as efficient nucleophiles for the diastereoselective addition to N-(tert-butanesulfinyl)imines
    Almansa, Raquel
    Guijarro, David
    Yus, Miguel
    [J]. TETRAHEDRON-ASYMMETRY, 2008, 19 (05) : 603 - 606
  • [6] Additions of organometallic reagents to C=N bonds: Reactivity and selectivity
    Bloch, R
    [J]. CHEMICAL REVIEWS, 1998, 98 (04) : 1407 - 1438
  • [7] Synthesis of fused bicyclic imidazoles by ring-closing metathesis
    Chen, YZ
    Dias, HVR
    Lovely, CJ
    [J]. TETRAHEDRON LETTERS, 2003, 44 (07) : 1379 - 1382
  • [8] The identification of pyrazolo[1,5-a]pyridines as potent p38 kinase inhibitors
    Cheung, Mui
    Harris, Philip A.
    Badiang, Jennifer G.
    Peckham, Gregory E.
    Chamberlain, Stanley D.
    Alberti, Michael J.
    Jung, David K.
    Harris, Stephanie S.
    Bramson, Neal H.
    Epperly, Andrea H.
    Stimpson, Stephen A.
    Peel, Michael R.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2008, 18 (20) : 5428 - 5430
  • [9] Asymmetric synthesis of chiral amines by highly diastereoselective 1,2-additions of organometallic reagents to N-tert-butanesulfinyl imines
    Cogan, DA
    Liu, GC
    Ellman, J
    [J]. TETRAHEDRON, 1999, 55 (29) : 8883 - 8904
  • [10] Synthesis of oxygen- and nitrogen-containing heterocycles by ring-closing metathesis
    Deiters, A
    Martin, SF
    [J]. CHEMICAL REVIEWS, 2004, 104 (05) : 2199 - 2238