Synthesis of novel fused tricyclic quinolones:: 4α,5-dihydro-1H-[1,2,4]triazino[1,6-α]quinoline-2,4,6(3H)-triones

被引:2
作者
Edmont, D [1 ]
Marot, C [1 ]
Chenault, J [1 ]
机构
[1] Univ Orleans, Inst Chim Organ & Analyt, F-45067 Orleans 2, France
关键词
D O I
10.1002/jhet.5570390608
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A versatile methodology to build the 1H-[1,2,4]triazino[1,6-a]quinoline-2,4,6(3H)-trione structure from methyl 6-fluoro4-oxo-1,4-dihydro-2-quinolinecarboxylate was developed. The method involves an N-amination followed by condensation of an aroyl isocyanate to form an alpha semicarbazidocarboxylate that readily cyclizes to the fused [1,2,4]triazino ring under ammonia/ethanol condition. Also, the reactivity of the [1,2,4]triazino ring thus obtained was studied.
引用
收藏
页码:1161 / 1165
页数:5
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共 26 条
[2]   SYNTHESIS AND BIOLOGICAL-ACTIVITY OF BENZOTHIAZOLO[3,2-A]QUINOLONE ANTIBACTERIAL AGENTS [J].
CHU, DTW ;
FERNANDES, PB ;
PERNET, AG .
JOURNAL OF MEDICINAL CHEMISTRY, 1986, 29 (08) :1531-1534
[3]  
CHU DTW, 1990, J HETEROCYCLIC CHEM, V27, P1191
[4]   SHORT SYNTHESES OF 1,2,3,5-TETRAHYDRO-5-OXOPYRROLO[1,2-A]QUINOLINE-4-CARBOXYLIC ACID AND 1,2,3,4-TETRAHYDRO-6H-6-OXOPYRIDO[1,2-A]QUINOLINE-5-CARBOXYLIC ACID-DERIVATIVES [J].
CHU, DTW ;
CLAIBORNE, AK .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1987, 24 (06) :1537-1539
[5]   SERIAL STUDY OF AS-TRIAZINES .14. STUDY OF SYNTHESIS AND TAUTOMETRY OF 3-PHENYL-5-TRIAZONES AND 6-PHENYL-5-TRIAZONES [J].
DAUNIS, J ;
JACQUIER, R ;
PIGIERE, C .
TETRAHEDRON, 1974, 30 (17) :3171-3175
[6]  
DOHMORI R, 1976, CHEM PHARM BULL, V24, P130
[7]  
Edmont D, 2001, SYNLETT, P833
[8]   A convenient procedure for N-amination of 4-oxo-1,4-dihydroquinolines [J].
Edmont, D ;
Buisson, Y ;
Treillard, P ;
Plisson, C ;
Chenault, J .
SYNTHETIC COMMUNICATIONS, 2000, 30 (02) :217-225
[9]  
GERSTER JF, Patent No. 3896131
[10]  
Greene T. W., 1991, PROTECTIVE GROUPS OR, P346