An efficient and facile synthesis of new tetracyclic fused pyrazolo[4,3-c][1,2,4]triazino[4,5-a]quinolin-4(5H)-ones

被引:4
|
作者
Gomaa, Mohsen A. -M. [1 ]
Ali, Huda A. [1 ]
机构
[1] Menia Univ, Dept Chem, Fac Sci, El Minia 61519, Egypt
关键词
Pyrazolo[4,3-c][1,2,4]triazino[4,5-a]quinolone; Amidrazone; (1,5-dihydro-3-methyl-5-oxo-1-phenyl-4H-pyrazol-4-ylidene)propanedinitrile; Dearomatization; NITROGEN SYSTEMS BEARING; POTENTIAL ANTI-HIV; ENANTIOSELECTIVE CONSTRUCTION; 1,3-DIPOLAR CYCLOADDITIONS; 1,2,4-TRIAZINE MOIETY; ANTICANCER DRUGS; AMIDRAZONES; FLUORINE;
D O I
10.1007/s11030-018-9849-9
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Reaction of amidrazones 1a-1i with (1,5-dihydro-3-methyl-5-oxo-1-phenyl-4H-pyrazol-4-ylidene)propanedinitrile (2) in ethyl acetate solution in one-step reaction led to the formation of unprecedented pyrazolo[4,3-c][1,2,4]triazino[4,5-a]quinolin-4(5H)-ones 3a-3g along with pyrazolo[4,3-c][1,2,4]triazino[4,5-a]quinolin-12b-oles 3h-3m in moderate to excellent yields. These novel heterocycles were formed via a Michael addition reaction followed by intramolecular cyclization via a dearomatization process.
引用
收藏
页码:969 / 977
页数:9
相关论文
共 50 条
  • [1] An efficient and facile synthesis of new tetracyclic fused pyrazolo[4,3-c][1,2,4]triazino[4,5-a]quinolin-4(5H)-ones
    Mohsen A.-M. Gomaa
    Huda A. Ali
    Molecular Diversity, 2018, 22 : 969 - 977
  • [2] Fused quinoline heterocycles VIII. Synthesis of polyfunctionally substituted pyrazolo[4,3-c]quinolin-4(5H)-ones
    Mekheimer, Ramadan Ahmed
    Refaey, Saeed M.
    Sadek, Kamal Usef
    Hameed, Afaf Mohamed Abdel
    Ibrahim, Mohamed Ashry
    Shah, Anamik
    JOURNAL OF CHEMICAL RESEARCH, 2008, (12) : 735 - 737
  • [3] Synthesis of fur[2,3-c]quinolin-4(5H)-ones
    Majumdar, KC
    Kundu, AK
    Biswas, P
    HETEROCYCLES, 1999, 51 (10) : 2399 - 2406
  • [4] SIMPLE METHOD FOR SYNTHESIS OF 5-METHYLOXAZOLO-[4,5-C]QUINOLIN-4(5H)-ONES
    MERCHANT, JR
    SHIRALI, SS
    BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1977, 50 (11) : 3075 - 3075
  • [5] PREPARATION AND REACTIONS OF PYRAZOLO[4,3-C]-PYRIDIN-4(5H)-ONES
    MAREI, MG
    AFINIDAD, 1993, 50 (443) : 55 - 58
  • [6] 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
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1992, 40 (12) : 3245 - 3252
  • [7] Access to Functionalized 3H-Pyrrolo[2,3-c]quinolin-4(5H)-ones and Thieno[2,3-c]quinolin-4(5H)-ones via Domino Reaction of 4-Alkynyl-3-bromoquinolin-2(1H)-ones
    Wang, Zhiyong
    Xue, Lijun
    He, Yiyi
    Weng, Licong
    Fang, Ling
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (20): : 9628 - 9638
  • [8] 4-hydroxyquinolones-2. 36. Synthesis of 2-R-oxazolo[4,5-c]quinolin-4(5H)ones
    Ukrainets, IV
    Taran, SG
    Sidorenko, LV
    Gorokhova, OV
    Turov, AV
    KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1997, (11): : 1536 - 1541
  • [9] Synthesis of pyrazolo[4,3-e][1,2,4]triazolo[4,3-c]pyrimidines
    Davoodnia, Abolghasem
    Zhiani, Rahele
    Tavakoli-Hoseini, Niloofar
    MONATSHEFTE FUR CHEMIE, 2008, 139 (11): : 1405 - 1407
  • [10] Synthesis of pyrazolo[4,3-e][1,2,4]triazolo[4,3-c]pyrimidines
    Abolghasem Davoodnia
    Rahele Zhiani
    Niloofar Tavakoli-Hoseini
    Monatshefte für Chemie - Chemical Monthly, 2008, 139 : 1405 - 1407