The synthesis and transformations of substituted 2-hydroxy-3-dimethylaminopropenoates. The preparation of condensed 3-hydroxypyran-2-ones

被引:43
作者
Smodis, J [1 ]
Stanovnik, B [1 ]
机构
[1] Univ Ljubljana, Dept Chem & Chem Technol, Ljubljana 1001, Slovenia
关键词
D O I
10.1016/S0040-4020(98)00534-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A convenient synthesis of substituted 2-hydroxy-3-dimethylaminopropenoates is reported. They react with cyclic 1,3-diketones, with aromatic and heteroaromatic hydroxy compounds to afford the corresponding 3-substituted hydroxytetrahydro-2H-1-benzopyran-2-ones, benzo- and naphthopyran-2-ones and azolo- and azinopyran-2-ones, respectively. Catalytic debenzylation of 3-benzyloxy substituted fused pyran-2-ones gives free 3-hydroxy derivatives. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:9799 / 9810
页数:12
相关论文
共 36 条
[1]  
AHLUWALIA VK, 1979, HETEROCYCLES, V12, P1203
[2]  
[Anonymous], 1993, PROG HETEROCYCL CHEM, DOI [10.1002/jhet.5570270247z(, DOI 10.1002/JHET.5570270247Z]
[3]   ORTHOAMIDES .26. SYNTHESIS AND REACTIONS OF 1,2-BIS(DIALKYLAMINO)ETHYLENES [J].
BREDERECK, H ;
SIMCHEN, G ;
GRIEBENOW, W .
CHEMISCHE BERICHTE-RECUEIL, 1974, 107 (05) :1545-1554
[4]   NEW ANTIALLERGIC PYRANO[3,2-G]QUINOLINE-2,8-DICARBOXYLIC ACIDS WITH POTENTIAL FOR THE TOPICAL TREATMENT OF ASTHMA [J].
CAIRNS, H ;
COX, D ;
GOULD, KJ ;
INGALL, AH ;
SUSCHITZKY, JL .
JOURNAL OF MEDICINAL CHEMISTRY, 1985, 28 (12) :1832-1842
[5]   2-(AMINOMETHYL)PHENOLS, A NEW CLASS OF SALURETIC AGENTS .5. FUSED-RING ANALOGS [J].
DEANA, AA ;
STOKKER, GE ;
SCHULTZ, EM ;
SMITH, RL ;
CRAGOE, EJ ;
RUSSO, HF ;
WATSON, LS .
JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (04) :580-585
[6]  
FEUER G, 1974, PROGR MED CHEM, P85
[7]  
Green G.R., 1996, COMPREHENSIVE HETERO, V5, P469, DOI 10.1016/B978-008096518-5.00112-X
[8]   3-5-DIOXO-1-2-DIPHENYLPYRAZOLIDINES - THE 4-HYDROXY-ANALOGUES AND CERTAIN 4-ALKOXY-ANALOGUES AND 4-ALKYLAMINO-ANALOGUES [J].
HAMMOND, KM ;
FISHER, N ;
MORGAN, EN ;
TANNER, EM .
JOURNAL OF THE CHEMICAL SOCIETY, 1957, (MAR) :1062-1067
[9]  
Hepworth J.D., 1984, COMPREHENSIVE HETERO, V3, P737, DOI DOI 10.1016/B978-008096519-2.00046-1
[10]  
Hepworth J. D., 1996, COMPREHENSIVE HETERO, V5, P351, DOI DOI 10.1016/B978-008096518-5.00111-8