Synthesis and further rearrangements of 7-(2-cycloalken-1-yl)-8-quinolinols

被引：2
|
作者：
Toerincsi, Mercedesz [1 ]
Kolonits, Pal [1 ]
Novak, Lajos [1 ]
机构：
[1] Budapest Univ Technol & Econ, Dept Organ Chem & Technol, Res Grp Alkaloid Chem, Hungarian Acad Sci, H-1111 Budapest, Hungary
来源：
MONATSHEFTE FUR CHEMIE | 2014年 / 145卷 / 06期
关键词：
Claisen rearrangement; Cyclization; Furo-quinoline; Oxecino-quinoline; Oxonino-quinoline; Ring constriction; RING-CLOSURE; DERIVATIVES; RULES;
D O I：
10.1007/s00706-014-1167-z
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Rearrangement reaction of 8-(cycloalkenyloxy)quinolines and the acid-catalyzed cyclization of the products were investigated. These reactions afforded insights on interesting new heterocyclic systems. Depending on the size of the cycloalkenyl moiety, we could isolate benzofuro [3,2-h]quinoline,methanooxecino[3,2-h] quinoline, methanooxonino[3,2-h]quinoline, and/or spiro[ cycloalkano-1,2'-furo[3,2-h]quinoline. The mechanism of the novel rearrangement reactions is also discussed.
引用
收藏
页码：993 / 999
页数：7
相关论文
共 50 条
  • [21] Practical synthesis of methyl 7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)-heptanoate
    Jiang, Xinpeng
    Wang, Xueyan
    Huang, Xing
    Li, Guizhou
    Yu, Chuanming
    JOURNAL OF SAUDI CHEMICAL SOCIETY, 2017, 21 (05) : 587 - 592
  • [22] SYNTHESIS AND PESTICIDAL ACTIVITY OF SUBSTITUTED 3-(1-AZA-1-CYCLOALKEN-2-YL)-3-PHENYL-1-METHYLUREAS
    JAVORSKY, P
    VESELA, Z
    TRUCHLIK, S
    CHEMICKE ZVESTI, 1978, 32 (02): : 223 - 231
  • [23] Synthesis of 3,1-benzoxazines from N-substituted ortho-(cycloalken-1-yl or alken-2-yl-2)anilines
    Gataullin, RR
    Afon'kin, IS
    Fatykhov, AA
    Abdrakhmanov, IB
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 2002, (03): : 367 - 371
  • [24] Synthesis of cyclometalated palladium (II) and platinum (II) complexes using 2-substituted 8-quinolinols containing C-donor atoms and steric interaction between the ligands
    Ohfuchi, S
    Kitamura, C
    Newkome, GR
    Yoneda, A
    NIPPON KAGAKU KAISHI, 2002, (02) : 201 - 210
  • [25] Ultrasound assisted, synthesis of N-(7-(R)-2-oxa-8-azabicyclo[4.2.0]octan-8-yl)isonicotinamide derivatives and their biological evaluation
    Chavan, Pravin
    Salve, Amol
    Jadhav, Shivaji
    Pansare, Dattatraya
    Rai, Megha
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2020, 57 (03) : 1228 - 1235
  • [26] Synthesis of quinolone analogues: 7-[(2S, 4R)-2-aminomethyl-4-hydroxypyrrolidin-1-yl] quinolones
    Liu, JY
    Guo, HY
    CHINESE CHEMICAL LETTERS, 2004, 15 (05) : 535 - 538
  • [27] Effect of further substitutions at 5-, 6-, 7-, or 8-position of 3-[3-(4-methoxyphenyl)-1-hydroxyprop-2-yl]coumarin on phytotoxicity
    Yamauchi, Satoshi
    Sartiva, Hazna
    Nishiwaki, Hisashi
    JOURNAL OF PESTICIDE SCIENCE, 2023, 48 (03) : 93 - 98
  • [28] Synthesis and in vitro antibacterial activities of 7-(4-alkoxyimino-3-hydroxypiperidin-1-yl)quinolone derivatives
    Wang, Ju Xian
    Guo, Qiang
    Chai, Yun
    Feng, Lian Shun
    Guo, Hui Yuan
    Liu, Ming Liang
    CHINESE CHEMICAL LETTERS, 2010, 21 (01) : 55 - 58
  • [29] Synthesis of Quinolone Analogues: 7-[(2S,4R)-2-Aminomethyl-4- hydroxypyrrolidin-1-yl] Quinolones
    Jiu Yu LIU
    Chinese Chemical Letters, 2004, (05) : 535 - 538
  • [30] COMPONENT FATTY-ACIDS OF DELONIX-REGIA SEED OIL - A SOURCE OF 7-(2-OCTACYCLOPROPEN-1-YL)HEPTANOIC ACID AND 8-(2-OCTACYCLOPROPEN-1-YL)OCTANOIC ACID
    HOSAMANI, KM
    HOSAMANI, SK
    FETT WISSENSCHAFT TECHNOLOGIE-FAT SCIENCE TECHNOLOGY, 1995, 97 (11): : 420 - 422
12345