Synthesis of Methyl 3-Azidothieno[2,3-b]pyridine-2-carboxylates and Application of the Huisgen Reaction

被引:8
作者
Chaouni, Wafaa [1 ,2 ]
Aadil, Mina [2 ]
Djellal, Ahmed [1 ]
Kirsch, Gilbert [1 ]
机构
[1] Univ Lorraine, Inst Jean Barriol, UMR 7565, SRMSC,LIMBP, F-57070 Metz, France
[2] FST Mohammedia, LCBA, Mohammadia 20800, Morocco
来源
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES | 2014年 / 69卷 / 05期
关键词
Vilsmeier-Haack-Arnold Reaction; 2-Chloro-3-cyano-pyridines; Thienopyridines; 1,2,3-Triazole; HERPESVIRUS POLYMERASES; BIOLOGICAL EVALUATION; DERIVATIVES; INHIBITORS; PYRIDOTHIENOPYRIMIDINES; PYRIDOTHIENOTRIAZINES; PYRIDINES; DESIGN; AGENTS;
D O I
10.5560/ZNB.2014-3320
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The preparation of new substituted methyl 3-azidothieno[2,3-b]pyridine carboxylates by azotization of methyl 3-aminothieno[2,3-b]pyridine and subsequent treatment with sodium azide is described. Via Huisgen's 1,3-dipolar cycloaddition between substituted alkynes and the prepared azides, methyl 1,2,3-triazolo-thieno[2,3-b]pyridine carboxylates have been obtained.
引用
收藏
页码:509 / 518
页数:10
相关论文
共 29 条
  • [1] Aacker D. S., 1962, J AM CHEM SOC, V84, P3370
  • [2] SYNTHESIS OF NEW 3-AMINOTHIENO[2,3-B]PYRIDINE AND SELENO[2,3-B]PYRIDINE DERIVATIVES
    AADIL, M
    KIRSCH, G
    [J]. PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1993, 82 (1-4): : 91 - 97
  • [3] Abdel-Rahman AE, 2003, PHARMAZIE, V58, P372
  • [4] Anderson M. W., 1961, J CHEM SOC, P4705
  • [5] [Anonymous], 1984, 1,3 -Dipolar Cycloaddition Chemistry
  • [6] Synthesis and antidiabetic activity of 2,5-disubstituted-3-imidazol-2-yl-pyrrolo[2,3-b]pyridines and thieno[2,3-b]pyridines
    Bahekar, Rajesh H.
    Jain, Mukul R.
    Jadav, Pradip A.
    Prajapati, Vijay M.
    Patel, Dipam N.
    Gupta, Arun A.
    Sharma, Ajay
    Tom, Robby
    Bandyopadhya, Debdutta
    Modi, Honey
    Patel, Pankaj R.
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (21) : 6782 - 6795
  • [7] THE SYNTHESIS OF EMETINE AND RELATED COMPOUNDS .2. THE SYNTHESIS OF (+/-)-RUBREMETINIUM BROMIDE
    BATTERSBY, AR
    OPENSHAW, HT
    WOOD, HCS
    [J]. JOURNAL OF THE CHEMICAL SOCIETY, 1953, (AUG): : 2463 - 2470
  • [8] A CONVENIENT METHOD FOR PREPARATION OF 3-CYANO-6-METHYL-2(1H)PYRIDONE
    BINOVI, LJ
    ARLT, HG
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (05) : 1656 - &
  • [9] NONPEPTIDIC INHIBITORS OF HUMAN-LEUKOCYTE ELASTASE .2. DESIGN, SYNTHESIS, AND IN-VITRO ACTIVITY OF A SERIES OF 3-AMINO-6-ARYLOPYRIDIN-2-ONE TRIFLUOROMETHYL KETONES
    DAMEWOOD, JR
    EDWARDS, PD
    FEENEY, S
    GOMES, BC
    STEELMAN, GB
    TUTHILL, PA
    WILIIAMS, JC
    WARNER, P
    WOOLSON, SA
    WOLANIN, DJ
    VEALE, CA
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (20) : 3303 - 3312
  • [10] Eldin SM, 1999, Z NATURFORSCH B, V54, P674