Efficient large scale microwave assisted Mannich reactions using substituted acetophenones

被引：46

作者：

Lehmann, Fredrik ^{[1
]}

Pilotti, Ake ^{[2
,3
]}

Luthman, Kristina ^{[1
]}

机构：

[1] Univ Gothenburg, Dept Chem Med Chem, Gothenburg, Sweden

[2] Stockholm Univ, Dept Organ Chem, S-10691 Stockholm, Sweden

[3] Personal Chem, Uppsala, Sweden

来源：

MOLECULAR DIVERSITY | 2003年 / 7卷 / 2-4期

关键词：

large scale; Mannich reaction; microwave chemistry; substituted acetophenones;

D O I：

10.1023/B:MODI.0000006809.48284.ed

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A series of substituted acetophenones, paraformaldehyde, and symmetrical dialkylamines were used in microwave enhanced Mannich reactions. Appropriate reaction conditions in terms of choice of solvent, reaction temperature, and reaction time were studied to allow a fast and reproducible production of Mannich bases. Both small ( 2 mmol) and large scale reactions ( 40 mmol) were performed successfully, providing a series of substituted Mannich bases in moderate to high yields and high purity.

引用

页码：145 / 152

页数：8

共 37 条

[1]

Arend M, 1998, ANGEW CHEM INT EDIT, V37, P1044, DOI 10.1002/(SICI)1521-3773(19980504)37:8<1044::AID-ANIE1044>3.0.CO

[2]

2-E

[3] HOST GUEST COMPLEXATION .53. FUNCTIONAL-GROUPS PREORGANIZED IN HEMISPHERANDS FOR BINDING ALKALI-METAL AND AMMONIUM CATIONS [J].

BRYANT, JA ;

HELGESON, RC ;

KNOBLER, CB ;

DEGRANDPRE, MP ;

CRAM, DJ .

JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (15) :4622-4634

[4] 6-(SUBSTITUTED PHENYL)-5-METHYL-4,5-DIHYDROPYRIDAZIN-3(2H)-ONES OF MEDICINAL INTEREST - THE SYNTHESIS OF SK AND F-94836 AND SK AND F-95654 [J].

BURPITT, BE ;

CRAWFORD, LP ;

DAVIES, BJ ;

MISTRY, J ;

MITCHELL, MB ;

PANCHOLI, KD ;

COATES, WJ .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1988, 25 (06) :1689-1695

[5] DEVELOPMENT AND APPLICATION OF A CONTINUOUS MICROWAVE REACTOR FOR ORGANIC-SYNTHESIS [J].

CABLEWSKI, T ;

FAUX, AF ;

STRAUSS, CR .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (12) :3408-3412

[6] THE SYNTHESIS OF INDAN-1-ONES AND ISOCOUMARINS [J].

CARTER, RH ;

GARSON, MJ ;

HILL, RA ;

STAUNTON, J ;

SUNTER, DC .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (02) :471-479

[7] SYNTHESIS OF 1,4-DIKETONES BY FLUORIDE-CATALYZED MICHAEL ADDITION AND SUPPORTED PERMANGANATE OXIDATION [J].

CLARK, JH ;

CORK, DG .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1982, (11) :635-636

[8] Application of focused microwaves to the scale-up of solvent-free organic reactions [J].

Cléophax, J ;

Liagre, M ;

Loupy, A ;

Petit, A .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2000, 4 (06) :498-504

[9] 1,4-BIS(3-OXO-2,3-DIHYDROPYRIDAZIN-6-YL)BENZENE ANALOGS - POTENT PHOSPHODIESTERASE INHIBITORS AND INODILATORS [J].

COATES, WJ ;

PRAIN, HD ;

REEVES, ML ;

WARRINGTON, BH .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (06) :1735-1741

[10]

Esveld E, 2000, CHEM ENG TECHNOL, V23, P279, DOI 10.1002/(SICI)1521-4125(200003)23:3<279::AID-CEAT279>3.0.CO

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