Zolimidine Analogues: The Synthesis of Imidazo[1,2-α]pyridine-Based Sulfilimines and Sulfoximines

被引：22
作者：
Hendriks, Christine M. M. [1 ]
Nuernberg, Pinchas [1 ]
Bolm, Carsten [1 ]
机构：
[1] Rhein Westfal TH Aachen, Inst Organ Chem, D-52074 Aachen, Germany
来源：
SYNTHESIS-STUTTGART | 2015年 / 47卷 / 08期
关键词：
imidazo[1,2-alpha]pyridine; sulfoximine; sulfilimine; zolimidine; imination; DERIVATIVES; SULFOXIDES; INHIBITOR; IMINATION; SULFIDES; TRIFLATE; ACCESS;
D O I：
10.1055/s-0034-1380109
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Zolimidine is a methylsulfonyl-substituted drug with an imidazo[1,2-]pyridine core used for the treatment of peptic ulcer. Herein, we report the synthesis of unprecedented N-acetylsulfilimine and -sulfoximine analogues under mild conditions. Deprotection of the N-acetylsulfoximine allows the preparation of the corresponding NH-sulfoximine.
引用
收藏
页码：1190 / 1194
页数：5
相关论文
共 63 条
  • [1] SYNTHESIS AND ORAL ANTIALLERGIC ACTIVITY OF CARBOXYLIC-ACIDS DERIVED FROM IMIDAZO[2,1-C][1,4]BENZOXAZINES, IMIDAZO[1,2-A]QUINOLINES, IMIDAZO[1,2-A]QUINOXALINES, IMIDAZO[1,2-A]QUINOXALINONES, PYRROLO[1,2-A]QUINOXALINONES, PYRROLO[2,3-A]QUINOXALINONES, AND IMIDAZO[2,1-B]BENZOTHIAZOLES
    AGER, IR
    BARNES, AC
    DANSWAN, GW
    HAIRSINE, PW
    KAY, DP
    KENNEWELL, PD
    MATHARU, SS
    MILLER, P
    ROBSON, P
    ROWLANDS, DA
    TULLY, WR
    WESTWOOD, R
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1988, 31 (06) : 1098 - 1115
  • [2] DERIVATIVES OF IMIDAZOLE .I. SYNTHESIS AND REACTIONS OF IMIDAZO[1,2-A]PYRIDIENES WITH ANALGESIC ANTIINFLAMMATORY ANTIPYRETIC AND ANTICONVULSANT ACTIVITY
    ALMIRANTE, L
    POLO, L
    MUGNAINI, A
    PROVINCIALI, E
    RUGARLI, P
    BIANCOTTI, A
    GAMBA, A
    MURMANN, W
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1965, 8 (03) : 305 - +
  • [3] [Anonymous], SYNTHESIS
  • [4] [Anonymous], ORGANOSULFUR CHEM AS
  • [5] [Anonymous], 2012, J CHEM
  • [6] Synthesis of imidazo[1,2-a]pyridines: a decade update
    Bagdi, Avik Kumar
    Santra, Sougata
    Monir, Kamarul
    Hajra, Alakananda
    [J]. CHEMICAL COMMUNICATIONS, 2015, 51 (09) : 1555 - 1575
  • [7] Copper-Catalyzed Synthesis of Imidazo[1,2-a]pyridines through Tandem Imine Formation-Oxidative Cyclization under Ambient Air: One-Step Synthesis of Zolimidine on a Gram-Scale
    Bagdi, Avik Kumar
    Rahman, Matiur
    Santra, Sougata
    Majee, Adinath
    Hajra, Alakananda
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2013, 355 (09) : 1741 - 1747
  • [8] N-Fused Imidazoles As Novel Anticancer Agents That Inhibit Catalytic Activity of Topoisomerase IIα and Induce Apoptosis in G1/S Phase
    Baviskar, Ashish T.
    Madaan, Chetna
    Preet, Ranjan
    Mohapatra, Purusottam
    Jain, Vaibhav
    Agarwal, Amit
    Guchhait, Sankar K.
    Kundu, Chanakya N.
    Banerjee, Uttam C.
    Bharatam, Prasad V.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (14) : 5013 - 5030
  • [9] BELOHLAVEK D, 1979, SCAND J GASTROENTERO, V14, P44
  • [10] Light-Induced Ruthenium-Catalyzed Nitrene Transfer Reactions: A Photochemical Approach towards N-Acyl Sulfimides and Sulfoximines
    Bizet, Vincent
    Buglioni, Laura
    Bolm, Carsten
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (22) : 5639 - 5642
1234567