Synthesis of N-Alkyl-Substituted 4-Quinolones via Tandem Alkenyl and Aryl C-N Bond Formation

被引：40

作者：

Shao, Jun ^{[1
]}

Huang, Xiaomei ^{[1
]}

Hong, Xiaohu ^{[1
]}

Liu, Bingxin ^{[1
]}

Xu, Bin ^{[1
,2
,3
]}

机构：

[1] Shanghai Univ, Dept Chem, Shanghai 200444, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China

[3] E China Normal Univ, Dept Chem, Shanghai Key Lab Green Chem & Chem Proc, Shanghai 200062, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2012年 / 44卷 / 12期

基金：

中国国家自然科学基金;

关键词：

alkynes; amination; cyclization; nitrogen heterocycles; domino reactions; ONE-POT SYNTHESIS; ANTIMALARIAL ACTIVITY; CATALYZED AMIDATION; ANTITUMOR AGENTS; NS3; PROTEASE; CYCLIZATION; DERIVATIVES; QUINOLONE; 2-PHENYL-4-QUINOLONE; 2-ARYL-4-QUINOLONES;

D O I：

10.1055/s-0031-1290775

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

N-Alkyl-substituted 4-quinolones are present as the key structural motif in many marketed drugs. An efficient one-step tandem amination approach was developed to afford N-alkyl-substituted 4-quinolones in high yields from easily accessible o-chloroaryl acetylenic ketones and functionalized alkyl amines. The approach complements and extends our previous work. Compared with other reported methods, the current method provides a very simple and convenient route.

引用

页码：1798 / 1808

页数：11

共 43 条

[1] Reactivity of 3-Iodo-4-quinolones in Heck Reactions: Synthesis of Novel (E)-3-Styryl-4-quinolones [J].

Almeida, Andreia I. S. ;

Silva, Artur M. S. ;

Cavaleiro, Jose A. S. .

SYNLETT, 2010, (03) :462-466

[2] A General Copper Powder-Catalyzed Ullmann-Type Reaction of 3-Halo-4(1H)-quinolones With Various Nitrogen-Containing Nucleophiles [J].

Audisio, Davide ;

Messaoudi, Samir ;

Peyrat, Jean-Francois ;

Brion, Jean-Daniel ;

Alami, Mouad .

JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (12) :4995-5005

[3] 1,2-Disubstituted 4-Quinolones via Copper-Catalyzed Cyclization of 1-(2-Halophenyl)-2-en-3-amin-1-ones [J].

Bernini, Roberta ;

Cacchi, Sandro ;

Fabrizi, Giancarlo ;

Sferrazza, Alessio .

SYNTHESIS-STUTTGART, 2009, (07) :1209-1219

[4] THE METHODS OF SYNTHESIS, MODIFICATION, AND BIOLOGICAL ACTIVITY OF 4-QUINOLONES (REVIEW) [J].

Boteva, A. A. ;

Krasnykh, O. P. .

CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2009, 45 (07) :757-785

[5] A NOVEL SYNTHESIS OF CARBON-LABELED QUINOLONE-3-CARBOXYLIC ACID ANTIBACTERIALS [J].

CARR, RM ;

SUTHERLAND, DR .

JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS, 1994, 34 (10) :961-971

[6] THE CHEMISTRY OF 2H-3,1-BENZOXAZINE-2,4(1H)-DIONE (ISATOIC-ANHYDRIDE) .9. SYNTHESIS OF 2-ARYLQUINOLINE ALKALOIDS [J].

COPPOLA, GM .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1982, 19 (04) :727-731

[7] Divergent Route to Access Structurally Diverse 4-Quinolones via Mono or Sequential Cross-Couplings [J].

Cross, R. Matthew ;

Manetsch, Roman .

JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (24) :8654-8657

[8] Endochin Optimization: Structure-Activity and Structure-Property Relationship Studies of 3-Substituted 2-Methyl-4(1H)-quinolones with Antimalarial Activity [J].

Cross, R. Matthew ;

Monastyrskyi, Andrii ;

Mukta, Tina S. ;

Burrows, Jeremy N. ;

Kyle, Dennis E. ;

Manetsch, Roman .

JOURNAL OF MEDICINAL CHEMISTRY, 2010, 53 (19) :7076-7094

[9] Microwave-assisted rapid and straightforward synthesis of 2-aryl-4-quinolones from acylated 2′-aminoacetophenones [J].

Ding, Derong ;

Li, Xin ;

Wang, Xin ;

Du, Yongli ;

Shen, Jingkang .

TETRAHEDRON LETTERS, 2006, 47 (39) :6997-6999

[10] Ester prodrugs of ciprofloxacin as DNA-gyrase inhibitors: synthesis, antiparasitic evaluation and docking studies [J].

Dubar, Faustine ;

Wintjens, Rene ;

Martins-Duarte, Erica S. ;

Vommaro, Rossiane C. ;

de Souza, Wanderley ;

Dive, Daniel ;

Pierrot, Christine ;

Pradines, Bruno ;

Wohlkonig, Alexandre ;

Khalife, Jamal ;

Biot, Christophe .

MEDCHEMCOMM, 2011, 2 (05) :430-435

← 1 2 3 4 5 →