Synthesis of 3-iodopyrrolocoumarins via iodine-induced 5-endo-dig electrophilic cyclization

被引:7
作者
Majumdar, K. C. [1 ]
De, Nirupam [1 ]
Sinha, Biswajit [1 ]
Roy, B. [1 ]
机构
[1] Univ Kalyani, Dept Chem, Kalyani 741235, W Bengal, India
来源
MONATSHEFTE FUR CHEMIE | 2012年 / 143卷 / 07期
关键词
Molecular iodine; Electrophilic cyclization; 3-Iodopyrrolocoumarins; 5-endo-dig Cyclization; LAMELLARIN-ALPHA; 20-SULFATE; PYRROLOCOUMARIN DERIVATIVES; BIOLOGICAL-ACTIVITY; MOLECULAR-IODINE; IODOCYCLIZATION; INHIBITOR; AGENTS;
D O I
10.1007/s00706-011-0694-0
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient synthesis of 3-iodopyrrolocoumarins has been achieved by a simple and straightforward strategy involving palladium-copper-catalyzed Sonogashira coupling followed by iodocyclization at ambient temperature using molecular iodine as the electrophilic source. In addition, functionalization at the 3-position of the iodocyclized product is performed via Sonogashira reaction.
引用
收藏
页码:1067 / 1073
页数:7
相关论文
共 44 条
[1]   A simple, two-step synthesis of 3-iodoindoles [J].
Amjad, M ;
Knight, DW .
TETRAHEDRON LETTERS, 2004, 45 (03) :539-541
[2]   Synthesis of 2,4,5-trisubstituted 3-fluorofurans via sequential iodocyclization and cross-coupling of gem-difluorohomopropargyl alcohols [J].
Arimitsu, Satoru ;
Jacobsen, Jesse M. ;
Hammond, Gerald B. .
JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (07) :2886-2889
[3]  
Baldwin J, 1978, Ciba Found Symp, P85
[4]   5-ENDO-TRIGONAL REACTIONS - DISFAVORED RING-CLOSURE [J].
BALDWIN, JE ;
CUTTING, J ;
DUPONT, W ;
KRUSE, L ;
SILBERMAN, L ;
THOMAS, RC .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :736-738
[5]   RULES FOR RING-CLOSURE [J].
BALDWIN, JE .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736
[6]  
Barlett PA, 1984, ASYMMETRIC SYNTHESIS, P411
[7]   Synthesis and absolute stereochemistry assignment of enantiopure dihydrofuro- and dihydropyrano-quinoline alkaloids [J].
Boyd, DR ;
Sharma, ND ;
Barr, SA ;
Carroll, JG ;
Mackerracher, D ;
Malone, JF .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (20) :3397-3405
[8]   Iodocyclization reactions for the desymmetrization of cyclohexa-1,4-dienes [J].
Butters, M. ;
Elliott, M. C. ;
Hill-Cousins, J. ;
Paine, J. S. ;
Walker, J. K. E. .
ORGANIC LETTERS, 2007, 9 (18) :3635-3638
[9]   STEREOCONTROLLED CYCLOFUNCTIONALIZATIONS OF DOUBLE-BONDS THROUGH HETEROCYCLIC INTERMEDIATES [J].
CARDILLO, G ;
ORENA, M .
TETRAHEDRON, 1990, 46 (10) :3321-3408
[10]  
Carlos GJ, 2002, SYNTHESIS-STUTTGART, P475