Reaction of chromone-3-carbaldehyde with α-amino acids -: syntheses of 3- and 4-(2-hydroxybenzoyl)pyrroles

被引：31

作者：

Figueiredo, Andrea G. P. R. ^{[1
]}

Tome, Augusto C. ^{[1
]}

Silva, Artur M. S. ^{[1
]}

Cavaleiro, Jose A. S. ^{[1
]}

机构：

[1] Univ Aveiro, Dept Chem, P-3810193 Aveiro, Portugal

来源：

TETRAHEDRON | 2007年 / 63卷 / 04期

关键词：

azomethine ylides; benzoylpyrroles; 1,5-electrocyclizations; 1,3-dipolar cycloadditions; chromones;

D O I：

10.1016/j.tet.2006.11.034

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Azomethine ylides generated from the reaction of chromone-3-carbaldehyde with a-amino acids undergo 1,5-electrocyclization reactions to afford 3- and 4-(2-hydroxybenzoyl)pyrroles. These ylides can be trapped with dipolarophiles in 1,3-dipolar cycloaddition reactions to yield chromonyl pyrrolidines. The reaction of chromone-3-carbaldehyde with methyl glycinate gives a mixture of pyrrole, pyridine, and 3-aza-9-xanthenone derivatives. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：910 / 917

页数：8

共 24 条

[1] STUDIES IN CHROMONE DERIVATIVES - CYCLO-ADDITION REACTIONS OF 4-OXO 4H-1-BENZOPYRAN-3-CARBOXALDEHYDE IMINES WITH BENZONITRILE OXIDE AND NITRILIMINE OF 4-OXO-4H-1-BENZOPYRAN-3-CARBOXALDEHYDE WITH ALKENES [J].

BARUAH, AK ;

PRAJAPATI, D ;

SANDHU, JS .

TETRAHEDRON, 1988, 44 (04) :1241-1246

[2] STUDIES ON CHROMONE DERIVATIVES - NOVEL 1,3 DIPOLAR CYCLOADDITIONS OF 4-OXO-1-BENZOPYRAN-3-CARBALDEHYDE IMINES AND IMINE OXIDES [J].

BARUAH, AK ;

PRAJAPATI, D ;

SANDHU, JS .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1987, (09) :1995-1998

[3] REACTIONS OF FORMYLCHROMONE DERIVATIVES .5. TRANSFORMATIONS OF 3-FORMYLCHROMONES INTO PYRROLES AND PYRIDINES [J].

CLARKE, PD ;

FITTON, AO ;

KOSMIRAK, M ;

SUSCHITZKY, H ;

SUSCHITZKY, JL .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (08) :1747-1756

[4] CYCLOADDITIONS OF SUBSTITUTED BENZOPYRAN-4-ONES TO ELECTRON-RICH DIENES - A NEW ROUTE TO XANTHONE DERIVATIVES [J].

CREMINS, PJ ;

SAENGCHANTARA, ST ;

WALLACE, TW .

TETRAHEDRON, 1987, 43 (13) :3075-3082

[5] [60]Fullerene-flavonoid dyads [J].

de la Torre, MDL ;

Rodrigues, AGP ;

Tomé, AC ;

Silva, AMS ;

Cavaleiro, JAS .

TETRAHEDRON, 2004, 60 (16) :3581-3592

[6] ISOMERIC BENZOYLPYRROLEACETIC ACIDS - SOME STRUCTURAL ASPECTS FOR ALDOSE REDUCTASE INHIBITORY AND ANTIINFLAMMATORY ACTIVITIES [J].

DEMOPOULOS, VJ ;

REKKA, E .

JOURNAL OF PHARMACEUTICAL SCIENCES, 1995, 84 (01) :79-82

[7]

FITTON AO, 1977, SYNTHESIS-STUTTGART, P133

[8] TRANSFORMATION OF 3-FORMYLCHROMONES INTO PYRIDINES AND PYRROLES [J].

FITTON, AO ;

KOSMIRAK, M ;

SUSCHITZKY, H ;

SUSCHITZKY, JL .

TETRAHEDRON LETTERS, 1982, 23 (38) :3953-3956

[9]

GHOSH CK, 1987, INDIAN J CHEM B, V26, P423

[10]

Ghosh CK, 2004, HETEROCYCLES, V63, P2875

← 1 2 3 →