Molecular Iodine Mediated Intramolecular Cyclization: An Efficient Method for the Synthesis of Benzoxepine Derivatives

被引:21
作者
Majumdar, K. C. [1 ]
Sinha, Biswajit [1 ]
Ansary, Inul [1 ]
Chakravorty, Santanu [1 ]
机构
[1] Univ Kalyani, Dept Chem, Kalyani 741235, W Bengal, India
关键词
iodine; intramolecular cyclization; benzoxepine; electrophile; 7-exo cyclization; MEDIUM-RING HETEROCYCLES; ELECTROPHILIC CYCLIZATION; OXA-HETEROCYCLES; NATURAL-PRODUCTS; PTERULINIC ACID; HECK REACTION; OLEFIN; NADH; 3-IODOINDOLES; METABOLITES;
D O I
10.1055/s-0029-1219825
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A simple, efficient and cost effective method for a divergent synthesis of benzoxepine derivatives using a hitherto unreported, highly regioselective, tandem iodocyclization procedure is described.
引用
收藏
页码:1407 / 1411
页数:5
相关论文
共 65 条
[1]   A synthetic entry to furo[2,3-b]pyridin-4(1H)-ones and related furoquinolinones via iodocyclization [J].
Aillaud, I ;
Bossharth, E ;
Conreaux, D ;
Desbordes, P ;
Monteiro, N ;
Balme, G .
ORGANIC LETTERS, 2006, 8 (06) :1113-1116
[2]  
Alcaide B, 1998, EUR J ORG CHEM, V1998, P2913
[3]   Stereoselective synthesis of substituted 2,5-diazabicyclo[2.2.1]heptanes by iodine-mediated cyclization of optically pure compounds containing the 4,5-diamino-1,7-octadiene and 1,2-diamino-4-alkene moieties [J].
Alvaro, Giuseppe ;
Di Fabio, Romano ;
Gualandi, Andrea ;
Morelli, Claudio ;
Monari, Magda ;
Savoia, Diego ;
Zoli, Luca .
TETRAHEDRON, 2007, 63 (50) :12446-12453
[4]   A simple, two-step synthesis of 3-iodoindoles [J].
Amjad, M ;
Knight, DW .
TETRAHEDRON LETTERS, 2004, 45 (03) :539-541
[5]   A new approach to 2,3-disubstituted benzo[b]furans from o-alkynylphenols via 5-endo-dig-iodocyclisation/palladium-catalysed reactions [J].
Arcadi, A ;
Cacchi, S ;
Fabrizi, G ;
Marinelli, F ;
Moro, L .
SYNLETT, 1999, (09) :1432-1434
[6]   Synthesis of medium ring heterocycles using an intramolecular Heck reaction [J].
Arnold, LA ;
Luo, WC ;
Guy, RK .
ORGANIC LETTERS, 2004, 6 (17) :3005-3007
[7]   A brief synthesis of beta-iodofurans [J].
Bew, SP ;
Knight, DW .
CHEMICAL COMMUNICATIONS, 1996, (09) :1007-1008
[8]   Synthesis of the Oxepinochromone Natural Products Ptaeroxylin (Desoxykarenin), Ptaeroxylinol, and Eranthin [J].
Bruder, Marjorie ;
Haseler, Paul L. ;
Muscarella, Marina ;
Lewis, William ;
Moody, Christopher J. .
JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (02) :353-358
[9]  
CAMPELLO MJ, 1982, TETRAHEDRON LETT, V23, P239
[10]   NEW OXIDIZED ISOCULARINE ALKALOIDS FROM SARCOCAPNOS PLANTS [J].
CAMPELLO, MJ ;
CASTEDO, L ;
DOMINGUEZ, D ;
DELERA, AR ;
SAA, JM ;
SUAU, R ;
TOJO, E ;
VIDAL, MC .
TETRAHEDRON LETTERS, 1984, 25 (51) :5933-5936