Synthesis of new dehydro 2-azatryptophans and derivatives via Heck cross-coupling reactions of 3-iodoindazoles with methyl 2-(acetylamino)acrylate

被引：29
|
作者：
Crestey, Francois [1 ]
Collot, Valerie [1 ]
Stiebing, Silvia [1 ]
Rault, Sylvain [1 ]
机构：
[1] Univ Caen, CERMN, UPRES, EA3915,UFR Sci Pharmaceut, F-14032 Caen, France
来源：
SYNTHESIS-STUTTGART | 2006年 / 20期
关键词：
dehydro; 2-azatryptophans; protective amino acid derivatives; catalytic hydrogenation; Heck cross-coupling reaction; 3-iodoindazoles; 2-(acetylamino)acrylate;
D O I：
10.1055/s-2006-950242
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
This paper describes the Heck cross-coupling reaction of 3-iodoindazoles with methyl 2-(acetylamino)acrylate as a general route to new dehydro 2-azatryptophans and protected amino acid derivatives after catalytic hydrogenation.
引用
收藏
页码：3506 / 3514
页数：9
相关论文
共 50 条
  • [31] Synthesis of 2-Aryl-4H-thiochromen-4-one Derivatives via a Cross-Coupling Reaction
    Li, Peng
    Li, Shengnan
    Li, Gang
    Huang, Haihong
    [J]. ACS OMEGA, 2021, 6 (22): : 14655 - 14663
  • [32] rac-BINAP-PdCl2 catalyzed Heck reactions of 3-formylquinolin-2-yl chlorides with methyl acrylate: synthesis of methyl 3-(3-formylquinolin-2-yl) acrylates
    Sharma, Neha
    Asthana, Mrityunjaya
    Kumar, Ritush
    Mishra, Kalpana
    Singh, Radhey M.
    [J]. TETRAHEDRON LETTERS, 2014, 55 (15) : 2348 - 2351
  • [33] 5-Pyrimidylboronic acid and 2-methoxy-5-pyrimidylboronic acid:: new heteroarylpyrimidine derivatives via Suzuki cross-coupling reactions
    Saygili, N
    Batsanov, AS
    Bryce, MR
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (06) : 852 - 857
  • [34] Synthesis of 3-aryl and 3-heterocyclic quinoxalin-2-ylamines via Pd-catalyzed cross-coupling reactions
    Li, JJ
    Yue, WS
    [J]. TETRAHEDRON LETTERS, 1999, 40 (24) : 4507 - 4510
  • [35] New asymmetric synthesis of protein farnesyltransferase inhibitors via palladium-catalyzed cross-coupling reactions of 2-iodo-imidazoles
    Kerherve, Jennifer
    Botuha, Candice
    Dubois, Joelle
    [J]. ORGANIC & BIOMOLECULAR CHEMISTRY, 2009, 7 (10) : 2214 - 2222
  • [36] Palladium-Catalyzed Decarboxylative Csp2-Csp2 Cross-Coupling Reactions: An Efficient Route for Synthesis of Azaisoflavone Derivatives
    Xia, Chengcai
    Yang, Yong
    Wei, Zhenjiang
    Yu, Wenbo
    Liao, Hanxiao
    Shen, Chao
    Zhang, Pengfei
    [J]. CATALYSIS LETTERS, 2015, 145 (08) : 1634 - 1642
  • [37] Stereoselective synthesis of (3E)-2-stannyl-1,3-dienes via palladium catalysed cross-coupling reactions
    Cai, MZ
    Li, HG
    Hao, WY
    [J]. JOURNAL OF CHEMICAL RESEARCH-S, 2005, (02): : 103 - 104
  • [38] Regioselective palladium-catalyzed cross-coupling reactions in the synthesis of novel 2,3-disubstituted thiophene derivatives
    Pereira, R
    Iglesias, B
    de Lera, AR
    [J]. TETRAHEDRON, 2001, 57 (37) : 7871 - 7881
  • [39] Synthesis of 3-alkyl-6-methyl-1,2,4,5-tetrazines via a Sonogashira-type cross-coupling reaction
    Ros, Enric
    Prades, Amparo
    Forson, Dominique
    Smyth, Jacqueline
    Verdaguer, Xavier
    Ribas de Pouplana, Lluis
    Riera, Antoni
    [J]. CHEMICAL COMMUNICATIONS, 2020, 56 (75) : 11086 - 11089
  • [40] Synthesis of 3-aryl and 3-heterocyclic quinoxalin-2-ylamines via palladium-catalyzed cross-coupling reactions.
    Li, JJ
    Yue, WS
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1999, 218 : U216 - U217
12345