New straightforward quinoline synthesis from the Mannich reaction of α-ketohydrazones

被引：16

作者：

Bailliez, V ^{[1
]}

El Kaim, L ^{[1
]}

Michaut, V ^{[1
]}

机构：

[1] Ecole Natl Super Tech Avancees, Lab Chim & Proc, F-75015 Paris, France

来源：

SYNTHETIC COMMUNICATIONS | 2004年 / 34卷 / 01期

关键词：

azo-Friedlander reaction; quinoline; Mannich reaction; alpha-ketohydrazone;

D O I：

10.1081/SCC-120027244

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The addition of alpha-ketohydrazones to 2-acetamidobenzaldehyde proceeds efficiently in the presence of N-benzylpiperazine to afford in good to high yields the expected Mannich adducts; these are easily converted to quinoline derivatives under acidic conditions in a new Azo-Friedlander reaction.

引用

页码：109 / 118

页数：10

共 20 条

[1] A new green approach to the Friedlander synthesis of quinolines [J].

Arcadi, A ;

Chiarini, M ;

Di Giuseppe, S ;

Marinelli, F .

SYNLETT, 2003, (02) :203-206

[2]

Atlan V, 2002, SYNLETT, P352

[3] The use of hydrazones for efficient mannich type coupling with aldehydes and secondary amines [J].

Atlan, V ;

Bienaymé, H ;

El Kaim, L ;

Majee, A .

CHEMICAL COMMUNICATIONS, 2000, (17) :1585-1586

[4] MICHAEL ADDITIONS OF HYDRAZONES FOR CARBON CARBON BOND FORMATION [J].

BALDWIN, JE ;

ADLINGTON, RM ;

BOTTARO, JC ;

JAIN, AU ;

KOLHE, JN ;

PERRY, MWD ;

NEWINGTON, IM .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (16) :1095-1096

[5] AZO ANIONS IN SYNTHESIS .1. TERT-BUTYLHYDRAZONES AS ACYL-ANION EQUIVALENTS [J].

BALDWIN, JE ;

ADLINGTON, RM ;

BOTTARO, JC ;

KOLHE, JN ;

PERRY, MWD ;

JAIN, AU .

TETRAHEDRON, 1986, 42 (15) :4223-4234

[6]

BODENDORF K, 1959, LIEBIGS ANN CHEM, V623, P109

[7] Porphyrin synthesis in surfactant solution: Multicomponent assembly in micelles [J].

BonarLaw, RP .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (11) :3623-3634

[8]

CHENG CC, 1982, ORG REACTIONS, V28, P37

[9]

Delgado J.N., 1991, WILSON GISVOLDS TXB

[10] Electrophilic and nucleophilic reactivities of the azomethine carbon of SAMP-hydrazones:: Stereoselective synthesis of γ-amino ketone derivatives [J].

Enders, D ;

Díez, E ;

Fernández, R ;

Martín-Zamora, E ;

Muñoz, JM ;

Pappalardo, RR ;

Lassaletta, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (17) :6329-6336

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