New environmentally-friendly solvent-free synthesis of imines using calcium oxide under microwave irradiation

被引：53

作者：

Gopalakrishnan, M. ^{[1
]}

Sureshkumar, P. ^{[1
]}

Kanagarajan, V. ^{[1
]}

Thanusu, J. ^{[1
]}

机构：

[1] Annamalai Univ, Dept Chem, Annamalainagar 608002, Tamil Nadu, India

来源：

RESEARCH ON CHEMICAL INTERMEDIATES | 2007年 / 33卷 / 06期

关键词：

calcium oxide; imines; solvent-free conditions; microwave irradiation; green chemistry;

D O I：

10.1163/156856707782565822

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Condensation of structurally diverse aldehydes including heterocyclic aldehydes, like furfural, with various amines in the presence of calcium oxide affording the corresponding imines in solvent-free conditions in good to excellent yields under microwave irradiation is described. A comparative study has been done under thermal conditions. The synergy between dry media and microwave irradiation in this reaction is evaluated by condensing less electrophilic aldehydes with poorly nucleophilic amines. The main advantages of this environmentally friendly protocol are the use of the non-toxic and inexpensive reagent calcium oxide and the considerable rate enhancement in comparison with a thermal reaction.

引用

页码：541 / 548

页数：8

共 21 条

[1] NON-DECARBOXYLATIVE 1,3-DIPOLAR CYCLOADDITIONS OF IMINES OF ALPHA-AMINO-ACIDS AS A ROUTE TO PROLINE DERIVATIVES [J].

ALY, MF ;

YOUNES, MI ;

METWALLY, SAM .

TETRAHEDRON, 1994, 50 (10) :3159-3168

[2]

ANDRADE Z, 2004, SYNLETT, V12, P2135

[3]

[Anonymous], 1989, Adv. Heterocycl. Chem, DOI DOI 10.1016/S0065-2725(08)60332-3

[4]

Bergbreiter D.E., 1983, ASYMMETRIC SYNTHESIS, V2A, P243

[5] REDUCTION OF SCHIFF BASES .2. BENZHYDRYLAMINES AND STRUCTURALLY RELATED COMPOUNDS [J].

BILLMAN, JH ;

TAI, KM .

JOURNAL OF ORGANIC CHEMISTRY, 1958, 23 (04) :535-539

[6] THE RAPID SYNTHESIS OF ORGANIC-COMPOUNDS IN MICROWAVE-OVENS [J].

GEDYE, RN ;

SMITH, FE ;

WESTAWAY, KC .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1988, 66 (01) :17-26

[7] Aluminium metal powder (atomized) catalyzed Friedel-Crafts acylation in solvent-free conditions: A facile and rapid synthesis of aryl ketones under microwave irradiation [J].

Gopalakrishnan, M ;

Sureshkumar, P ;

Kanagarajan, V ;

Thanusu, J .

CATALYSIS COMMUNICATIONS, 2005, 6 (12) :753-756

[8] Silica gel supported sodium hydrogen sulfate as an efficient and reusable heterogeneous catalyst for the synthesis of imines in solvent-free conditions under microwave irradiation [J].

Gopalakrishnan, M ;

Sureshkumar, P ;

Kanagarajan, V ;

Thanusu, J ;

Govindaraju, R .

JOURNAL OF CHEMICAL RESEARCH, 2005, (05) :299-303

[9] Organic synthesis in solid media. Alumina supported sodium hydrogen sulfate as an effective and reusable catalyst for 'one-pot' synthesis of amides from ketones in dry media under microwave irradiation [J].

Gopalakrishnan, M ;

Sureshkumar, P ;

Kanagarajan, V ;

Thanusu, J .

LETTERS IN ORGANIC CHEMISTRY, 2005, 2 (05) :444-446

[10]

Hadjipavlou-litina D.J., 1996, DRUG DESIGN DISCOV, V15, P199

← 1 2 3 →