A one-pot synthesis of 1,2,4,5-tetraarylimidazoles using molecular iodine as an efficient catalyst

被引：97

作者：

Kidwai, Mazaahir ^{[1
]}

Mothsra, Poonam ^{[1
]}

机构：

[1] Univ Delhi, Dept Chem, Green Chem Res Lab, Delhi 110007, India

来源：

TETRAHEDRON LETTERS | 2006年 / 47卷 / 29期

关键词：

molecular iodine; benzoin; benzil; 1,2,4,5-tetraarylimidazoles;

D O I：

10.1016/j.tetlet.2006.05.097

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Molecular iodine is a cheap, nontoxic catalyst, which acts as an efficient catalyst for the synthesis of 1,2,4,5-tetraarylimidazoles using benzoin, an aromatic aldehyde and an amine in the presence of ammonium acetate. The advantage of this method is the direct use of benzoin, which is transformed into benzil in situ and condenses further to generate the imidazole in a one-pot sequence. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：5029 / 5031

页数：3

共 23 条

[1] Synthesis, structure, and photophysical properties of polyarylated imidazoles and oxazoles [J].

Buttke, K ;

Baumgartel, H ;

Niclas, HJ ;

Schneider, M .

JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 1997, 339 (08) :721-728

[2] An efficient synthesis of tetrasubstituted imidazoles from N-(2-oxo)-amides [J].

Claiborne, CF ;

Liverton, NJ ;

Nguyen, KT .

TETRAHEDRON LETTERS, 1998, 39 (49) :8939-8942

[3]

CLARK NG, 1975, TETRAHEDRON LETT, P2717

[4]

CONSONNI R, 1991, J CHEM RES-S, P188

[5] Solid-phase synthesis of terminal oligonucleotide-phosphoramidate conjugates [J].

Cooke, LA ;

Frauendorf, C ;

Gîlea, MA ;

Holmes, SC ;

Vyle, JS .

TETRAHEDRON LETTERS, 2006, 47 (05) :719-722

[6] Oxidation of benzoins to diketones with iodine [J].

Corson, BB ;

McAllister, RW .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1929, 51 :2822-2825

[7] The action of ammonia on benzil [J].

Davidson, D ;

Weiss, M ;

Jelling, M .

JOURNAL OF ORGANIC CHEMISTRY, 1937, 2 (04) :319-327

[8] SYNTHESIS OF DIPHTHAMIDE - THE TARGET OF DIPHTHERIA-TOXIN CATALYZED ADP-RIBOSYLATION IN PROTEIN-SYNTHESIS ELONGATION FACTOR-II [J].

EVANS, DA ;

LUNDY, KM .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (04) :1495-1496

[9] Synthesis of substituted imidazoles via organocatalysis [J].

Frantz, DE ;

Morency, L ;

Soheili, A ;

Murry, JA ;

Grabowski, EJJ ;

Tillyer, RD .

ORGANIC LETTERS, 2004, 6 (05) :843-846

[10] A NEW SYNTHESIS OF TETRAARYLIMIDAZOLES AND PENTAARYLIMIDAZOLIUM SALTS [J].

HEINZE, J ;

BAUMGART.H ;

ZIMMERMA.H .

CHEMISCHE BERICHTE-RECUEIL, 1968, 101 (10) :3504-&

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