An Efficient Synthesis of Dibenzo[b,f]oxepins by Ring-Closing Metathesis

被引:16
作者
Bharath, Yada [1 ]
Thirupathi, Barla [1 ]
Ranjit, Gurram [1 ]
Mohapatra, Debendra K. [1 ]
机构
[1] Indian Inst Chem Technol, CSIR, Nat Prod Chem Div, Hyderabad 500007, Andhra Pradesh, India
关键词
Bauhinia; dibenzo[b; f]oxepins; 2,2 '-oxybis(vinylbenzenes); ring-closing metathesis; Ullmann reaction; ULLMANN-TYPE SYNTHESIS; 1ST TOTAL-SYNTHESIS; DIARYL ETHERS; ARYL IODIDES; C-N; COPPER; DERIVATIVES; ARTOCARPOL; CATALYSTS; PHENOLS;
D O I
10.1002/ajoc.201300141
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Dibenzo[b,f]oxepin scaffolds, which have been found in the Bauhinia plant family and have potent medicinal properties, have been prepared efficiently by a two-step protocol that involves Ullmann-type coupling and ring-closing metathesis reactions.
引用
收藏
页码:848 / 851
页数:4
相关论文
共 95 条
[1]   TRICYCLIC TRIARYLETHYLENE ANTI-ESTROGENS - DIBENZ[B,F]OXEPINS, DIBENZO[B,F]THIEPINS, DIBENZO[A,E]CYCLOOCTENES, AND DIBENZO[B,F]THIOCINS [J].
ACTON, D ;
HILL, G ;
TAIT, BS .
JOURNAL OF MEDICINAL CHEMISTRY, 1983, 26 (08) :1131-1137
[2]   STUDIES IN THE WAGNER-MEERWEIN REARRANGEMENT .2. [J].
ANET, FAL ;
BAVIN, PMG .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1957, 35 (10) :1084-1087
[3]   PACHARIN - A NEW DIBENZO(2,3-6,7)OXEPIN DERIVATIVE FROM BAUHINIA-RACEMOSA LAMK [J].
ANJANEYULU, ASR ;
REDDY, AVR ;
REDDY, DSK ;
WARD, RS ;
ADHIKESAVALU, D ;
CAMERON, TS .
TETRAHEDRON, 1984, 40 (21) :4245-4252
[4]  
[Anonymous], 2006, ANGEW CHEM
[5]   Synthesis of medium ring heterocycles using an intramolecular Heck reaction [J].
Arnold, LA ;
Luo, WC ;
Guy, RK .
ORGANIC LETTERS, 2004, 6 (17) :3005-3007
[6]   ELECTROPHILIC SUBSTITUTION OF DIBENZ[B,F]OXEPIN [J].
BAVIN, PMG ;
BARTLE, KD ;
JONES, DW .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1968, 5 (03) :327-&
[7]   In an attempt to provide a user's guide to the galaxy of benzylidene, alkoxybenzylidene, and indenylidene ruthenium olefin metathesis catalysts [J].
Bieniek, Micho ;
Michrowska, Anna ;
Usanov, Dmitry L. ;
Grela, Karol .
CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (03) :806-818
[8]   SECOCULARINES - A NEW GROUP OF ISOQUINOLINE RELATED ALKALOIDS PRESENT IN THE FUMARIACEAE [J].
BOENTE, JM ;
CASTEDO, L ;
DOMINGUEZ, D ;
FARINA, A ;
DELERA, AR ;
VILLAVERDE, MC .
TETRAHEDRON LETTERS, 1984, 25 (08) :889-892
[9]   Ullmann diaryl ether synthesis: Rate acceleration by 2,2,6,6-tetramethylheptane-3,5-dione [J].
Buck, E ;
Song, ZJ ;
Tschaen, D ;
Dormer, PG ;
Volante, RP ;
Reider, PJ .
ORGANIC LETTERS, 2002, 4 (09) :1623-1626
[10]   1,1,1-tris(hydroxymethyl)ethane as a new, efficient, and versatile tripod ligand for copper-catalyzed cross-coupling reactions of aryl iodides with amides, thiols, and phenols [J].
Chen, Yao-Jung ;
Chen, Hsin-Hung .
ORGANIC LETTERS, 2006, 8 (24) :5609-5612