Ethyl 1,4-Dihydro-4-oxo-1,8-naphthyridine-3-carboxylates by a Tandem SNAr-Addition-Elimination Reaction

被引：11

作者：

Bunce, Richard A. ^{[1
]}

Nammalwar, Baskar ^{[1
]}

机构：

[1] Oklahoma State Univ, Dept Chem, Stillwater, OK 74078 USA

来源：

JOURNAL OF HETEROCYCLIC CHEMISTRY | 2012年 / 49卷 / 03期

关键词：

ANTIBACTERIAL AGENTS; QUINOLONES; ACIDS;

D O I：

10.1002/jhet.917

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A series of N-substituted 1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate esters has been prepared in two steps from ethyl 2-(2-chloronicotinoyl)acetate. Treatment of the beta-ketoester with N,N-dimethylformamide dimethyl acetal in N,N-dimethylformamide (DMF) gave a 95% yield of the 2-dimethylaminomethylene derivative. Subsequent reaction of this beta-enaminone with primary amines in DMF at 120oC for 24 h then afforded the target compounds in 4782% yields by a tandem SNAr-addition-elimination reaction. Synthetic and procedural details as well as a mechanistic rationale are presented.

引用

页码：658 / 663

页数：6

共 24 条

[1]

Albaneze-Walker J., 2005, TETRAHEDRON, V61, P6330

[2] Ethyl (1R*,3aS*,7aS*)-octahydro-7a-methyl-7-oxo-1H-indene-1-acetate using tandem reactions [J].

Bunce, RA ;

Harris, CR .

SYNTHETIC COMMUNICATIONS, 1996, 26 (10) :1969-1975

[3] A RING EXPANSION PROCEDURE BASED ON THE TANDEM DEALKOXYCARBONYLATION MICHAEL ADDITION-REACTION [J].

BUNCE, RA ;

SCHILLING, CL .

JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (09) :2748-2752

[4] Five- and six-membered lactones and lactams by tandem dealkoxycarbonylation Michael addition reactions [J].

Bunce, RA ;

Schilling, CL .

TETRAHEDRON, 1997, 53 (28) :9477-9486

[5] FUNCTIONALIZED CARBOCYCLES BY TANDEM DEALKOXYCARBONYLATION MICHAEL ADDITION-REACTIONS [J].

BUNCE, RA ;

DOWDY, ED ;

JONES, PB ;

HOLT, EM .

JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (25) :7143-7148

[6] 2,2,3-trisubstituted tetrahydrofurans and 2H-tetrahydropyrans by tandem demethoxycarbonylation Michael addition reactions [J].

Bunce, RA ;

Dowdy, ED ;

Childress, RS ;

Jones, PB .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (01) :144-151

[7] Ethyl 1,4-Dihydro-4-oxo-3-quinolinecarboxylates by a Tandem Addition-Elimination-SNAr Reaction [J].

Bunce, Richard A. ;

Lee, Eric J. ;

Grant, Matthew T. .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 2011, 48 (03) :620-625

[8] SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF NEW ARYLFLUORONAPHTHYRIDINE ANTIBACTERIAL AGENTS [J].

CHU, DTW ;

FERNANDES, PB ;

CLAIBORNE, AK ;

GRACEY, EH ;

PERNET, AG .

JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (11) :2363-2369

[9] PREPARATION AND INVITRO AND INVIVO EVALUATION OF QUINOLONES WITH SELECTIVE ACTIVITY AGAINST GRAM-POSITIVE ORGANISMS [J].

COOPER, CS ;

KLOCK, PL ;

CHU, DTW ;

HARDY, DJ ;

SWANSON, RN ;

PLATTNER, JJ .

JOURNAL OF MEDICINAL CHEMISTRY, 1992, 35 (08) :1392-1398

[10] SYNTHESIS AND BIOLOGICAL-ACTIVITY OF 5-AMINOOXYQUINOLENE AND 5-HYDROXYQUINOLONE, AND THE OVERWHELMING INFLUENCE OF THE REMOTE N1-SUBSTITUENT IN DETERMINING THE STRUCTURE ACTIVITY RELATIONSHIP [J].

DOMAGALA, JM ;

BRIDGES, AJ ;

CULBERTSON, TP ;

GAMBINO, L ;

HAGEN, SE ;

KARRICK, G ;

PORTER, K ;

SANCHEZ, JP ;

SESNIE, JA ;

SPENSE, FG ;

SZOTEK, D ;

WEMPLE, J .

JOURNAL OF MEDICINAL CHEMISTRY, 1991, 34 (03) :1142-1154

← 1 2 3 →