L-proline catalyzed multicomponent reactions: facile access to 2H-benzo[g]pyrazolo[3,4-b]-quinoline-5,10(4H,11H)-dione derivatives

被引：37
|
作者：
Karamthulla, Shaik [1 ]
Pal, Suman [1 ]
Parvin, Tasneem [2 ]
Choudhury, Lokman H. [1 ]
机构：
[1] Indian Inst Technol Patna, Dept Chem, Patna 800013, Bihar, India
[2] Natl Inst Technol Patna, Dept Chem, Patna 800005, Bihar, India
来源：
RSC ADVANCES | 2014年 / 4卷 / 29期
关键词：
ONE-POT SYNTHESIS; 3-COMPONENT REACTION; SPIROOXINDOLE DERIVATIVES; POLYCYCLIC HETEROCYCLES; REACTIONS DIVERSITY; VERSATILE CATALYST; MOLECULAR-IODINE; ATOM-ECONOMY; EFFICIENT; PYRAZOLOQUINOLINE;
D O I：
10.1039/c4ra00876f
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A series of 2H-benzo[g]pyrazolo[3,4-b]quinoline-5,10(4H,11H)-dione derivatives has been synthesized from the three component reactions of 2-hydroxy-1,4-naphthoquinone, aldehydes, and aminopyrazoles in the presence of a catalytic amount of L-proline. This domino reaction proceeds smoothly in good to excellent yields and offers several advantages including no column chromatography, a simple reaction procedure, metal-free reaction conditions and being applicable to a broad range of aldehydes.
引用
收藏
页码：15319 / 15324
页数：6
相关论文
共 50 条
  • [41] Mild Bronsted basic ionic liquids catalyzed three component synthesis of pyrazolo[1,2-a][1,2,4]triazole-1,3-dione and 2-amino-3-cyano-5,10-dioxo-4-phenyl-5,10-dihydro-4H-benzo[g]chromene derivatives
    Shaterian, H. R.
    Kangani, M.
    SCIENTIA IRANICA, 2013, 20 (03) : 571 - 579
  • [42] 10-(4-Chlorophenyl)-14a-hydroxy-12methyl-8,9,9a,10,12,13,14,14a-octahydro-5H-10a,14-methanoindeno[20,10:4,5]azepino[3,4-b]pyrrolizine5,15(7H,11H)-dione
    Nagalakshmi, R. A.
    Suresh, J.
    Malathi, K.
    Kumar, R. Ranjith
    Lakshman, P. L. Nilantha
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2014, 70 : O97 - +
  • [43] 14a-Hydroxy-12-methy1-10-(4-methylphenyl)-8,9,9a,10,12,13,14,14a-octa-hydro-10a,14-methano-5H-indeno-[2 ',1 ':4,5]azepino[3,4-b]pyrrolizine-5,15(7H,11H)-dione
    Nagalakshmi, R. A.
    Suresh, J.
    Malathi, K.
    Kumar, R. Ranjith
    Lakshman, P. L. Nilantha
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2013, 69 : O1581 - +
  • [44] Synthesis of Bioactive 3,4-Dihydro-2H-naphtho[2,3-b][1,4]oxazine-5,10-dione and 2,3,4,5-Tetrahydro-1H-naphtho[2,3-b]azepine-6,11-dione Derivatives via the Copper-Catalyzed Intramolecular Coupling Reaction
    You, Hengyao
    Vegi, Srinivas Rao
    Lagishetti, Chandraiah
    Chen, Shuo
    Reddy, R. Santhosh
    Yang, Xiaohong
    Guo, Jian
    Wang, Chenhui
    He, Yun
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (07): : 4119 - 4130
  • [45] 3,4a-Dichloro-10a-(3-chloro-6-hydroxy-2,2,6-trimethylcyclohexylmethyl)-6,8-dihydroxy-2,2,7-trimethyl-3,4,4a,10a-tetrahydro-2H-benzo[g]chromene-5,10-dione
    Soria-Mercado, IE
    Jensen, PR
    Fenical, W
    Kassel, S
    Golen, J
    ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2004, 60 : O1627 - O1629
  • [46] Hexahydrospiro-pyrazolo[3,4-b]pyridine-4,1-pyrrolo[3,2,1-ij]quinolines Derived from 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1,2-dione
    Saatluo, Bahman Ebrahimi
    Baradarani, Mehdi M.
    Joule, John A.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2018, 55 (05) : 1176 - 1182
  • [47] Poly(4-vinylpyridinium) hydrogen sulfate catalyzed synthesis of 12-aryl-12-hydro-5H-benzo[g]indeno[2,1-b]quinoline-6,11,13-trione derivatives
    Nader Ghaffari Khaligh
    Taraneh Mihankhah
    Research on Chemical Intermediates, 2015, 41 : 4569 - 4579
  • [48] Poly(4-vinylpyridinium) hydrogen sulfate catalyzed synthesis of 12-aryl-12-hydro-5H-benzo[g]indeno[2,1-b]quinoline-6,11,13-trione derivatives
    Khaligh, Nader Ghaffari
    Mihankhah, Taraneh
    RESEARCH ON CHEMICAL INTERMEDIATES, 2015, 41 (07) : 4569 - 4579
  • [49] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF SOME 5-SUBSTITUTED 1,2,5A,11B,11C-HEXAHYDRO[1]BENZOPYRANS[4,3-D]PYRAZOLO-[3,4-B]PYRIDINE-1,6-DIONES AND 5H-4A,10B-DIHYDROBENZOPYRANS-[3,4-C]PYRIDINE DERIVATIVES
    GOHAR, AKMN
    ABDELLATIF, FF
    ELKTATNY, MS
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1986, 25 (04): : 404 - 406
  • [50] Synthesis of benzo[6,7][1,4]diazepino[1,2-b]indazol-7(6H)-ones and benzo[f]pyrazolo[1,5-a][1,4]diazepin-4-ones via CuI/L-proline catalyzed intramolecular N2-arylation
    Wang, Hong-Jun
    Camara, Fatoumata
    Haber, James C., Jr.
    Mangette, John E.
    TETRAHEDRON LETTERS, 2015, 56 (08) : 1030 - 1033
12345