A convenient approach towards 2-and 3-aminobenzo[b]thiophenes

被引:24
|
作者
Androsov, Dmitry A. [1 ,2 ]
Solovyev, Andrey Y. [2 ]
Petrov, Mikhail L. [1 ]
Butcher, Ray J. [3 ]
Jasinski, Jerry P. [4 ]
机构
[1] Str Petersburg State Inst Technol, Dept Organ Chem, St Petersburg 190013, Russia
[2] Bowling Green State Univ, Ctr Photochem Sci, Bowling Green, OH 43403 USA
[3] Howard Univ, Dept Chem, Washington, DC 20059 USA
[4] Keene State Coll, Dept Chem, Keene, NH 03435 USA
关键词
PALLADIUM-CATALYZED AMINATION; WILLGERODT-KINDLER REACTION; ESTROGEN-RECEPTOR MODULATORS; ONE-POT SYNTHESIS; SECONDARY-AMINES; 1,2,3-THIADIAZOLES; EFFICIENT; DERIVATIVES; MECHANISM; BASE;
D O I
10.1016/j.tet.2010.01.069
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of 1-(2-chloro-5-nitrophenyl)ethanone via Willgerodt-Kindler route with primary or secondary amines and Sulfur allows a simple, efficient one-pot synthesis of 3-aminobenzo[b]thiophenes. Base-catalyzed transformation of 4-(2-chloro-5-nitrophenyl)-1,2,3-thiadiazole in the presence of primary and secondary amines offers a convenient approach towards 2-aminobenzo[b]thiophenes. (C) 2010 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2474 / 2485
页数:12
相关论文
共 50 条
  • [1] 3-AMINOBENZO(B)FURANS
    GEWALD, K
    JANSCH, HJ
    JOURNAL FUR PRAKTISCHE CHEMIE, 1973, 315 (04): : 779 - 785
  • [2] DYEING PROPERTIES OF DISPERSE DYES DERIVED FROM SUBSTITUTED 3-AMINOBENZO[B]THIOPHENES
    NISHIDA, K
    KONDO, H
    IGARASHI, K
    ANDO, Y
    MORIMOTO, T
    IWAMOTO, H
    TODA, H
    JOURNAL OF THE SOCIETY OF DYERS AND COLOURISTS, 1978, 94 (06): : 262 - 263
  • [3] Synthesis and biological evaluation of 2-and 3-aminobenzo[b]thiophene derivatives as antimitotic agents and inhibitors of tubulin polymerization
    Romagnoli, Romeo
    Baraldi, Pier Giovanni
    Carrion, Maria Dora
    Cara, Carlota Lopez
    Preti, Delia
    Fruttarolo, Francesca
    Pavani, Maria Giovanna
    Tabrizi, Mojgan Aghazadeh
    Tolomeo, Manlio
    Grimaudo, Stefania
    Di Cristina, Antonella
    Balzarini, Jan
    Hadfield, John A.
    Brancale, Andrea
    Hamel, Ernest
    JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (09) : 2273 - 2277
  • [4] Reactivity of several deactivated 3-aminobenzo[b]thiophenes in the Buchwald-Hartwig C-N coupling. Scope and limitations
    Queiroz, Maria-Joao R. P.
    Calhelha, Ricardo C.
    Kirsch, Gilbert
    TETRAHEDRON, 2007, 63 (52) : 13000 - 13005
  • [5] TRICYCLIC SYSTEMS OBTAINED FROM SOME 3-AMINOBENZO [B] THIOPHENE DERIVATIVES
    CLARKE, K
    FOX, WR
    SCROWSTON, RM
    JOURNAL OF CHEMICAL RESEARCH-S, 1980, (02): : 33 - &
  • [6] Microwave-assisted synthesis of 3-aminobenzo[b]-thiophene scaffolds for the preparation of kinase inhibitors
    Bagley, Mark C.
    Dwyer, Jessica E.
    Molina, Maria D. Beltran
    Rand, Alexander W.
    Rand, Hayley L.
    Tomkinson, Nicholas C. O.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (24) : 6814 - 6824
  • [7] One-pot synthesis of substituted 2-aminobenzo[b]thiophenes
    Solovyev, Andrey Y.
    Androsov, Dmitry A.
    Neckers, Douglas C.
    JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (08): : 3122 - 3124
  • [8] LITHIATION OF 3-AMINOBENZO[B]THIOPHENE AND 3-AMINOTHIOPHENE DERIVATIVES - APPLICATION TO THE SYNTHESIS OF BENZO[B]THIENOINDOLE AND THIENOINDOLE DERIVATIVES
    PRATS, M
    GALVEZ, C
    GASANZ, Y
    RODRIGUEZ, A
    JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (07): : 2184 - 2188
  • [9] SYNTHESIS OF 2-CYANO, 2-ACYL, AND 2-CARBOXAMIDO DERIVATIVES OF 3-AMINOBENZO[B]THIOPHENE INVOLVING NITRO DISPLACEMENT
    BECK, JR
    YAHNER, JA
    JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (23): : 3440 - 3441
  • [10] Organocatalytic stereoselective construction of polycyclic benzo[b]thiophenes from 2-aminobenzo[b]thiophenes and alkynyl-substituted enones
    Niu, Cheng
    Zheng, Yao
    Du, Da-Ming
    NEW JOURNAL OF CHEMISTRY, 2023, 47 (30) : 14515 - 14519