Efficient synthesis of novel N-substituted 2-carboxy-4-quinolones via lithium bis(trimethylsilyl) amide (LiHMDS)-induced in situ cyclocondensation reaction

被引：11

作者：

Hasan, Phool ^{[1
,2
]}

Aneja, Babita ^{[1
]}

Masood, Mir M. ^{[1
]}

Ahmad, Md. Belal ^{[2
]}

Yadava, Umesh ^{[3
]}

Daniliuc, Constantin G. ^{[4
]}

Abid, Mohammad ^{[1
,5
]}

机构：

[1] Jamia Millia Islamia, Dept Biosci, Med Chem Lab, New Delhi 110025, India

[2] TM Bhagalpur Univ, TNB Coll, Dept Chem, Bhagalpur 812007, Bihar, India

[3] Deen Dayal Upadhyay Gorakhpur Univ, Dept Phys, Gorakhpur 273009, Uttar Pradesh, India

[4] Westfalische Wilhelm Univ Munster, Inst Organ Chem, D-48149 Munster, Germany

[5] Univ Nebraska Med Ctr, Eppley Inst Res Canc & Allied Dis, Omaha, NE 68198 USA

来源：

RSC ADVANCES | 2017年 / 7卷 / 19期

关键词：

RECEPTOR ANTAGONISTS; CATALYZED AMIDATION; REDUCTIVE AMINATION; POTENT; AGENTS; 4-QUINOLONES; INHIBITORS; ANALOGS; OPTIMIZATION; DERIVATIVES;

D O I：

10.1039/c6ra28631c

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A different approach for the synthesis of N-substituted 2-carboxy-4-quinolones using direct reductive amination followed by LiHMDS-induced cyclocondensation has been developed. A range of analogues of the title compounds with broad substrate scope were obtained in moderate yields and good regioselectivity.

引用

页码：11367 / 11372

页数：6

共 34 条

[1] Reductive amination of aldehydes and ketones with sodium triacetoxyborohydride. Studies on direct and indirect reductive amination procedures
AbdelMagid, AF
Carson, KG
Harris, BD
Maryanoff, CA
Shah, RD
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) : 3849 - 3862
[2] Direct reductive amination of aldehydes and ketones using phenylsilane: Catalysis by dibutyltin dichloride
Apodaca, R
Xiao, W
[J]. ORGANIC LETTERS, 2001, 3 (11) : 1745 - 1748
[3] CYANOHYDRIDOBORATE ANION AS A SELECTIVE REDUCING AGENT
BORCH, RF
BERNSTEIN, MD
DURST, HD
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1971, 93 (12) : 2897 - +
[4] Kynurenic acid amides as novel NR2B selective NMDA receptor antagonists
Borza, Istvan
Kolok, Sandor
Galgoczy, Kornel
Gere, Aniko
Horvath, Csilla
Farkas, Sandor
Greiner, Istvan
Domany, Gyorgy
[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (02) : 406 - 409
[5] Design and Synthesis of 2-(3-Benzo[b]thienyl)-6,7-methylenedioxyquinolin-4-one Analogues as Potent Antitumor Agents that Inhibit Tubulin Assembly
Chang, Yu-Hsun
Hsu, Mei-Hua
Wang, Sheng-Hung
Huang, Li-Jiau
Qian, Keduo
Morris-Natschke, Susan L.
Hamel, Ernest
Kuo, Sheng-Chu
Lee, Kuo-Hsiung
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (15) : 4883 - 4891
[6] Rational Design of Partial Agonists for the Muscarinic M1 Acetylcholine Receptor
Chen, Xinyu
Kloeckner, Jessika
Holze, Janine
Zimmermann, Cornelia
Seemann, Wiebke K.
Schrage, Ramona
Bock, Andreas
Mohr, Klaus
Traenkle, Christian
Holzgrabe, Ulrike
Decker, Michael
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2015, 58 (02) : 560 - 576
[7] Multiple-Dose Safety, Tolerability, and Pharmacokinetics of Oral Nemonoxacin (TG-873870) in Healthy Volunteers
Chung, David T.
Tsai, Cheng-Yuan
Chen, Shu-Jen
Chang, Li-Wen
King, Chi-Hsin R.
Hsu, Ching-Hung
Chiu, Kit-Mui
Tan, Hao-Chen
Chang, Yu-Ting
Hsu, Ming-Chu
[J]. ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 2010, 54 (01) : 411 - 417
[8] Divergent Route to Access Structurally Diverse 4-Quinolones via Mono or Sequential Cross-Couplings
Cross, R. Matthew
Manetsch, Roman
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (24) : 8654 - 8657
[9] Endochin Optimization: Structure-Activity and Structure-Property Relationship Studies of 3-Substituted 2-Methyl-4(1H)-quinolones with Antimalarial Activity
Cross, R. Matthew
Monastyrskyi, Andrii
Mukta, Tina S.
Burrows, Jeremy N.
Kyle, Dennis E.
Manetsch, Roman
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (19) : 7076 - 7094
[10] DNA gyrase, topoisomerase IV, and the 4-quinolones
Drlica, K
Zhao, XL
[J]. MICROBIOLOGY AND MOLECULAR BIOLOGY REVIEWS, 1997, 61 (03) : 377 - +

← 1 2 3 4 →