Highly effective regioselective method for the synthesis of substituted coumarin- and quinolone-annulated heterocycles using a palladium(0)-catalyzed reaction

被引:34
作者
Majumdar, K. C. [1 ]
Pal, A. K. [1 ]
Taher, A. [1 ]
Debnath, P. [1 ]
机构
[1] Univ Kalyani, Dept Chem, Kalyani 741235, W Bengal, India
来源
SYNTHESIS-STUTTGART | 2007年 / 11期
关键词
Heck reaction; palladium(0) catalysis; tetracyclic ring system; regioselectivity;
D O I
10.1055/s-2007-966052
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The preparation of a variety of tetracyclic ring systems by palladium(O)-catalyzed cyclization of 2-bromobenzyloxy-substituted coumarins and quinolones is described. The process has been found to be a viable method for regioselective synthesis of the corresponding products in very good to excellent yield.
引用
收藏
页码:1707 / 1711
页数:5
相关论文
共 39 条
[21]   Regioselective synthesis of 1H,3H,6H[2]benzopyrano[4,3-d]pyrimidine-2,4-diones and 12H-benzopyrano[3,2-c][1]benzopyran-5-ones by radical cyclization [J].
Majumdar, KC ;
Basu, PK ;
Mukhopadhyay, PP ;
Sarkar, S ;
Ghosh, SK ;
Biswas, P .
TETRAHEDRON, 2003, 59 (12) :2151-2157
[22]   Carbon-carbon bond formation by radical cyclisation: Regioselective synthesis of coumarin-annulated sulfur heterocycles [J].
Majumdar, KC ;
Biswas, A ;
Mukhopadhyay, PP .
SYNTHESIS-STUTTGART, 2003, (15) :2385-2389
[23]  
Majumdar KC, 1996, J CHEM RES-S, P462
[24]  
Majumdar KC, 1997, HETEROCYCLES, V45, P1467
[25]   Studies in sigmatropic rearrangement: Synthesis of a [6,6]pyranothiopyran ring system by sequential Claisen rearrangement and pyridine hydrotribromide mediated regioselective "6-endo" cyclization [J].
Majumdar, KC ;
Kundu, UK ;
Ghosh, SK .
ORGANIC LETTERS, 2002, 4 (16) :2629-2631
[26]   Studies in pyrimidine-annelated heterocycles by tandem cyclization: Regioselective synthesis of [6,6]pyranopyran by intramolecular [1,6] Michael addition [J].
Majumdar, KC ;
Das, U .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (26) :9997-10000
[27]   Synthesis of bioactive heterocycles:: One pot regioselective synthesis of pyrano[3,2-f]benzo[b]thiophene derivatives. [J].
Majumdar, KC ;
Biswas, P .
TETRAHEDRON, 1999, 55 (05) :1449-1456
[28]   Regioselective synthesis of [6c,12b-cis]-6c,7,12,13-tetrahydro-1H-chromeno[3=B4,4=B4:4,5]pyrano[2,3-c]chromen-1-ones via unusual [1,6] Michael addition. [J].
Majumdar, KC ;
Chatterjee, P ;
Saha, S .
TETRAHEDRON LETTERS, 1998, 39 (39) :7147-7148
[29]  
MAJUMDAR KC, 1994, J CHEM SOC P1, V1, P2889
[30]   Efficient syntheses of 6-prenylcoumarins and linear pyranocoumarins:: Total synthesis of suberosin, toddaculin, O-methylapigravin (O-methylbrosiperin), O-methylbalsamiferone, dihydroxanthyletin, xanthyletin and luvangetin [J].
Mali, RS ;
Joshi, PP ;
Sandhu, PK ;
Manekar-Tilve, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (03) :371-376