Direct conversion of aldehydes to amides, tetrazoles, and triazines in aqueous media by one-pot tandem reactions

被引：150

作者：

Shie, JJ ^{[1
]}

Fang, JM ^{[1
]}

机构：

[1] Natl Taiwan Univ, Dept Chem, Taipei 106, Taiwan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2003年 / 68卷 / 03期

关键词：

D O I：

10.1021/jo026407z

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A variety of aldehydes reacted with iodine in ammonia water at room temperature to give the nitrile intermediates, which were trapped by addition of hydrogen peroxide, sodium azide, or dicyandiamide to produce their corresponding amides, tetrazoles, and 1,3,5-triazines in modest to high yields. The one-pot tandem reactions were conducted in water media, and the products were obtained simply by extraction or filtration.

引用

收藏

页码：1158 / 1160

页数：3

相关论文

共 45 条

[1] Fast microwave-assisted preparation of aryl and vinyl nitriles and the corresponding tetrazoles from organo-halides [J].

Alterman, M ;

Hallberg, A .

JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (23) :7984-7989

[2] The reduction of I2 by H2O2 in aqueous solution [J].

Ball, JM ;

Hnatiw, JB .

CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 2001, 79 (03) :304-311

[3] Langmuir films of an oligo(p-phenylene vinylene) functionalized with a diaminotriazine headgroup [J].

Balogh, DT ;

Dhanabalan, A ;

Dynarowicz-Latka, P ;

Schenning, APHJ ;

Oliveira, ON ;

Meijer, EW ;

Janssen, RAJ .

LANGMUIR, 2001, 17 (11) :3281-3285

[4] Hydrogen-bonded complexes of diaminopyridines and diaminotriazines: Opposite effect of acylation on complex stabilities [J].

Beijer, FH ;

Sijbesma, RP ;

Vekemans, JAJM ;

Meijer, EW ;

Kooijman, H ;

Spek, AL .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (18) :6371-6380

[5]

Brackman W., 1963, RECL TRAV CHIM PAY B, V82, P757

[6] Synthesis, structural characterization and antitumor activity of novel 2,4-diamino-1,3,5-triazine derivatives [J].

Brzozowski, Z ;

Saczewski, F ;

Gdaniec, M .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2000, 35 (12) :1053-1064

[7]

BUTLER RN, 1966, COMP HETEROCYCLIC CH, V4

[8] Synthesis of 6-aryl-2,4-diamino-pyrimidines and triazines using palladium catalysed Suzuki cross-coupling reactions [J].

Cooke, G ;

de Cremiers, HA ;

Rotello, VM ;

Tarbit, B ;

Vanderstraeten, PE .

TETRAHEDRON, 2001, 57 (14) :2787-2789

[9] Model systems for flavoenzyme activity. Molecular recognition of flavin at the polymer-liquid interface [J].

Deans, R ;

Rotello, VM .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (13) :4528-4529

[10] An intramolecular [2+3] cycloaddition route to fused 5-heterosubstituted tetrazoles [J].

Demko, ZP ;

Sharpless, KB .

ORGANIC LETTERS, 2001, 3 (25) :4091-4094

← 1 2 3 4 5 →