SYNTHESIS OF 1H-IMIDAZO[4,5-C]QUINOLIN-4(5H)-ONE VIA PALLADIUM-CATALYZED CYCLIZATION OF N-(2-BROMOPHENYL)-1H-IMIDAZOLE-4-CARBOXAMIDE

被引：47
|
作者：
KURODA, T [1 ]
SUZUKI, F [1 ]
机构：
[1] KYOWA HAKKO KOGYO CO LTD,PHARMACEUT RES LABS,1188 SHIMOTOGARI,NAGAIZUM CHO,SHIZUOKA 411,JAPAN
来源：
TETRAHEDRON LETTERS | 1991年 / 32卷 / 47期
关键词：
D O I：
10.1016/0040-4039(91)80443-A
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new heterocycle, 5-butyl-1-methyl-1H-imidazo[4,5-c]quinolin-4(5H)-one has been synthesized using palladium-catalyzed cyclization. A yield of the cyclization was optimized by changing base, additive and reaction temperature.
引用
收藏
页码：6915 / 6918
页数：4
相关论文
共 50 条
  • [1] SYNTHESIS OF IMIDAZO[4,5-C]QUINOLIN-4(5H)-ONE VIA RADICAL CYCLIZATION
    SUZUKI, F
    KURODA, T
    [J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 1993, 30 (03) : 811 - 813
  • [2] NEW BRONCHODILATORS .1. 1,5-SUBSTITUTED 1H-IMIDAZO[4,5-C]QUINOLIN-4(5H)-ONES
    SUZUKI, F
    KURODA, T
    NAKASATO, Y
    MANABE, H
    OHMORI, K
    KITAMURA, S
    ICHIKAWA, S
    OHNO, T
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (22) : 4045 - 4053
  • [3] NEW BRONCHODILATORS .2. 3H-IMIDAZO[4,5-C]QUINOLIN-4(5H)-ONES
    SUZUKI, F
    KURODA, T
    HAYASHI, H
    NAKASATO, Y
    MANABE, H
    OHMORI, K
    KITAMURA, S
    [J]. CHEMICAL & PHARMACEUTICAL BULLETIN, 1992, 40 (12) : 3245 - 3252
  • [4] Synthesis of 1-benzyl-8,9-dihydroimidazo[4,5-c]pyrrolo[3,2-g]quinolin-4(5H)-one via palladium-catalyzed intramolecular arylation
    Delest, B
    Tisserand, JY
    Robert, JM
    Nourrisson, MR
    Pinson, P
    Duflos, M
    Le Baut, G
    Renard, P
    Pfeiffer, B
    [J]. TETRAHEDRON, 2004, 60 (29) : 6079 - 6083
  • [5] 1-(2-methylpropyl)-1H-imidazo[4,5-c]-quinolin-4-amine
    Cheng, J
    Liu, ZM
    Yang, GF
    [J]. ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2005, 61 : O2638 - O2639
  • [6] SIMPLE METHOD FOR SYNTHESIS OF 5-METHYLOXAZOLO-[4,5-C]QUINOLIN-4(5H)-ONES
    MERCHANT, JR
    SHIRALI, SS
    [J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1977, 50 (11) : 3075 - 3075
  • [7] 1H-imidazo[4,5-c]quinoline derivatives as novel potent TNF-α suppressors:: Synthesis and structure-activity relationship of 1-, 2-and 4-substituted 1H-imidazo[4,5-c]quinolines or 1H-imidazo[4,5-c]pyridines
    Izumi, T
    Sakaguchi, J
    Takeshita, M
    Tawara, H
    Kato, K
    Dose, H
    Tsujino, T
    Watanabe, Y
    Kato, H
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2003, 11 (12) : 2541 - 2550
  • [8] 1H-IMIDAZO[4,5-C]QUINOLIN-4-AMINES - NOVEL NONXANTHINE ADENOSINE ANTAGONISTS
    VANGALEN, PJM
    NISSEN, P
    VANWIJNGAARDEN, I
    IJZERMAN, AP
    SOUDIJN, W
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (03) : 1202 - 1206
  • [9] Preparation of 2-aminosubstituted 3H-imidazo[4,5-c]quinolin-4(5H)-ones by palladium-assisted internal biaryl coupling reaction
    Ikuma, Yohei
    Nakahira, Hiroyuki
    [J]. TETRAHEDRON, 2011, 67 (49) : 9509 - 9517
  • [10] Discovery of 3H-imidazo[4,5-c]quinolin-4(5H)-ones as potent and selective dipeptidyl peptidase IV (DPP-4) inhibitors
    Ikuma, Yohei
    Hochigai, Hitoshi
    Kimura, Hidenori
    Nunami, Noriko
    Kobayashi, Tomonori
    Uchiyama, Katsuya
    Furuta, Yudai
    Sakai, Mutsuko
    Horiguchi, Masakuni
    Masui, Yumi
    Okazaki, Kazuhiko
    Sato, Yasuhiro
    Nakahira, Hiroyuki
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2012, 20 (19) : 5864 - 5883
12345