A NOVEL SYNTHETIC ROUTE TO 1,2-DIMETHYL-5-PHENYL-1H-IMIDAZO[4,5-B]PYRIDIN-7-OL

被引：1
|
作者：
LIS, R [1 ]
TRAINA, JA [1 ]
HUFFMAN, JC [1 ]
机构：
[1] INDIANA UNIV,CTR MOLEC STRUCT,BLOOMINGTON,IN 47405
来源：
JOURNAL OF HETEROCYCLIC CHEMISTRY | 1990年 / 27卷 / 03期
关键词：
D O I：
10.1002/jhet.5570270311
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Heating a mixture of 4‐amino‐1,2‐dimethyl‐1H‐imidazole‐5‐carboxylic acid ethyl ester with ethyl benzoyl acetate resulted in the formation of 8‐ethoxycarbonyl‐6,7‐dimethyl‐4‐oxo‐2‐phenylimidazo[1,5‐a]pyrimidin‐5‐ium, hydroxide, inner salt. This compound was then transformed into 1,2‐dimethyl‐5‐phenyl‐1H‐imidazo‐[4,5‐b]pyridin‐7‐ol via several intermediates. A number of structurally interesting compounds were also isolated during the course of this work. Thus, the target ring system was formed by a circuitous series of ring‐chain tautomerizations/rearrangements. Copyright © 1990 Journal of Heterocyclic Chemistry
引用
收藏
页码：531 / 534
页数：4
相关论文
共 50 条
  • [21] Synthesis and physical properties of pyrido[1′,2′ : 1,2]imidazo [4,5-b]quinoxalines
    Tomoda, H
    Saito, S
    Araki, K
    Shiraishi, S
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1998, 71 (05) : 1125 - 1135
  • [22] SYNTHESIS OF 2-ARYL-1H-IMIDAZO[4,5-B]INDOLES
    DANDIA, A
    GUPTA, A
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1994, 33 (11): : 1093 - 1095
  • [23] 3-Benzyl-6-bromo-1H-imidazo[4,5-b]pyridin-2(3H)-one
    Rodi, Youssef Kandri
    Haoudi, Amal
    Capet, Frederic
    Mazzah, Ahmed
    Essassi, El Mokhtar
    El Ammari, Lahcen
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O962 - +
  • [24] 3-Allyl-6-bromo-1H-imidazo[4,5-b]pyridin-2(3H)-one
    Dahmani, Siham
    Rodi, Youssef Kandri
    Luis, Santiago V.
    Bolte, Michael
    El Ammari, Lahcen
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O1998 - U182
  • [25] 6-Bromo-3-methyl-1H-imidazo[4,5-b]pyridin-2(3H)-one
    Ghacham, Hend Bel
    Rodi, Youssef Kandri
    Capet, Frederic
    Essassi, El Mokhtar
    Ng, Seik Weng
    ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2010, 66 : O1080 - U118
  • [26] Synthesis of 1-and 3-substituted imidazo[4,5-b]pyridin-2-ones
    Yu. M. Yutilov
    N. N. Smolyar
    D. A. Lomov
    Russian Journal of Organic Chemistry, 2006, 42 : 897 - 900
  • [27] Synthesis and Biological Activity Evaluation of Novel 5-Methyl-7-phenyl-3H-thiazolo[4,5-b]pyridin-2-ones
    Lozynskyi, Andrii
    Konechnyi, Yulian
    Senkiv, Julia
    Yushyn, Ihor
    Khyluk, Dmytro
    Karpenko, Olexandr
    Shepeta, Yulia
    Lesyk, Roman
    SCIENTIA PHARMACEUTICA, 2021, 89 (04)
  • [28] Crystal structure of 4-bromo-2-(1H-imidazo[4,5-b]pyridin-2-yl) phenol
    Ouari, Kamel
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2015, 71 : O991 - U925
  • [29] Synthesis of 1- and 3-substituted imidazo[4,5-b]pyridin-2-ones
    Yutilov, Yu. M.
    Smolyar, N. N.
    Lomov, A. A.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 42 (06) : 897 - 900
  • [30] NOVEL CAMP PDE-III INHIBITORS - IMIDAZO[4,5-B]PYRIDIN-2(3H)-ONES AND THIAZOLO[4,5-B]PYRIDIN-2(3H)-ONES AND THEIR ANALOGS
    SINGH, B
    BACON, ER
    ROBINSON, S
    FRITZ, RK
    LESHER, GY
    KUMAR, V
    DORITY, JA
    REUMAN, M
    KUO, GH
    EISSENSTAT, MA
    PAGANI, ED
    BODE, DC
    BENTLEY, RG
    CONNELL, MJ
    HAMEL, LT
    SILVER, PJ
    JOURNAL OF MEDICINAL CHEMISTRY, 1994, 37 (02) : 248 - 254
12345