A novel access to 2,4-substituted quinolines from acetylenic ketones

被引:25
作者
Masquelin, T [1 ]
Obrecht, D [1 ]
机构
[1] F HOFFMANN LA ROCHE & CO LTD,PHARMA RES,CH-4070 BASEL,SWITZERLAND
关键词
D O I
10.1016/S0040-4020(96)01025-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2, 4-Substituted quinolines of type 7 and 8 were synthesized starting from 2-amino thiophenol and acetylenic acetals 5 to yield various substituted benzo[b][1, 4] thiazepine intermediates of type 6. Subsequent sulfur extrusion in refluxing toluene led to 2, 4-substituted quinoline acetals 7, which were transformed into the corresponding 2-substituted quinoline-4-carbaldehydes 8 in good to excellent yields. Copyright (C) 1996 Elsevier Science Ltd
引用
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页码:641 / 646
页数:6
相关论文
共 13 条
[1]  
ALTALIB M, 1992, SYNTHESIS-STUTTGART, P875
[2]  
BARBOT F, 1979, TETRAHEDRON LETT, P4825
[3]  
Campbell N., 1976, RODDS CHEM CARBON F, VIVf, P231
[4]  
FRIEDLAENDER P, 1882, BER, V41, P4271
[5]   Solid-phase organic reactions: A review of the recent literature [J].
Hermkens, PHH ;
Ottenheijm, HCJ ;
Rees, D .
TETRAHEDRON, 1996, 52 (13) :4527-4554
[6]  
Knorr L., 1886, Justus Liebigs Ann. Chem, V236, P69
[7]   A FACILE PREPARATION OF 2-SUBSTITUTED AND 5-SUBSTITUTED 3-BROMOTHIOPHENES [J].
MASQUELIN, T ;
OBRECHT, D .
TETRAHEDRON LETTERS, 1994, 35 (50) :9387-9390
[8]  
MASQUELIN T, 1995, SYNTHESIS-STUTTGART, P276
[9]   NOVEL SYNTHESIS OF 2,4-DIPHENYLQUINOLINES [J].
NISHIO, T ;
KATAHIRA, K ;
OMOTE, Y .
TETRAHEDRON LETTERS, 1980, 21 (29) :2825-2826
[10]   A NEW METHOD FOR THE PREPARATION OF (E)-3-ACYLPROP-2-ENOIC ACIDS [J].
OBRECHT, D ;
WEISS, B .
HELVETICA CHIMICA ACTA, 1989, 72 (01) :117-122