FACILE AND CONVENIENT SYNTHESES OF FLUORINE-CONTAINING PYRIMIDO [5,4-c]QUINOLINES AND BENZO [h][1,6]NAPHTHYRIDINES BY CONDENSATION REACTION OF 2-METHOXY-3-TRIFLUOROACETYL-4-QUINOLYLAMINE WITH ALDEHYDES AND KETONES

被引：3

作者：

Hatakenaka, Mizuki ^{[1
]}

Okada, Etsuji ^{[1
]}

机构：

[1] Kobe Univ, Grad Sch Engn, Dept Chem Sci & Engn, Nada Ku, Rokkodai Cho, Kobe, Hyogo 6578501, Japan

来源：

HETEROCYCLES | 2017年 / 94卷 / 01期

关键词：

DERIVATIVES; ANTAGONISTS; QUINOLINES; DESIGN;

D O I：

10.3987/COM-16-13595

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

2-Methoxy-3-trifluoroacetyl-4-quinolylamine reacted easily with various aldehydes in the presence of aqueous ammonia to afford mainly trifluoromethylated pyrimido[5,4-c]quinoline derivatives in moderate to high yields. In contrast, the use of ketones instead of aldehydes in the presence of pyrrolidine, exclusively gave benzo[h][1,6]naphthyridine derivatives in good to excellent yields.

引用

页码：102 / 116

页数：15

共 43 条

[31] Discovery and SAR of 5-(3-Chlorophenylamino)benzo[c][2,6]naphthyridine-8-carboxylic Acid (CX-4945), the First Clinical Stage Inhibitor of Protein Kinase CK2 for the Treatment of Cancer [J].

Pierre, Fabrice ;

Chua, Peter C. ;

O'Brien, Sean E. ;

Siddiqui-Jain, Adam ;

Bourbon, Pauline ;

Haddach, Mustapha ;

Michaux, Jerome ;

Nagasawa, Johnny ;

Schwaebe, Michael K. ;

Stefan, Eric ;

Vialettes, Anne ;

Whitten, Jeffrey P. ;

Chen, Ta Kung ;

Darjania, Levan ;

Stansfield, Ryan ;

Anderes, Kenna ;

Bliesath, Josh ;

Drygin, Denis ;

Ho, Caroline ;

Omori, May ;

Proffitt, Chris ;

Streiner, Nicole ;

Trent, Katy ;

Rice, William G. ;

Ryckman, David M. .

JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (02) :635-654

[32]

RANADE A C, 1981, Indian Journal of Microbiology, V21, P159

[33]

Saito S., PCT Int. Appl, Patent No. [WO2006051704, 2006051704]

[34] Synthesis, antioxidant and toxicological study of novel pyrimido quinoline derivatives from 4-hydroxy-3-acyl quinolin-2-one [J].

Sankaran, Mathan ;

Kumarasamy, Chandraprakash ;

Chokkalingam, Uvarani ;

Mohan, Palathurai Subramaniam .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2010, 20 (23) :7147-7151

[35]

Stanczak A, 2001, PHARMAZIE, V56, P501

[36]

Stanczak A., STANCZAK A, Patent No. Pol., PL2003360568

[37]

Stevenson D. L., 1963, T NATL VAC S, V10, P134

[38]

Thangam R., 2013, J PHARM RES, V6, P532, DOI [DOI 10.1038/S41598-020-60541-1, 10.1016/J.JOPR.2013.04.042, DOI 10.1016/J.JOPR.2013.04.042]

[39]

Wissn A., PCT Int. Appi. WO, Patent No. 2008109599

[40]

Wu T. Y., PCT Int. Appl, Patent No. [WO2009111337, 2009111337]

← 1 2 3 4 5 →