Cu2O-catalyzed tandem ring-opening/coupling cyclization process for the synthesis of 2,3-dihydro-1,4-benzodioxins

被引:60
作者
Bao, Weiliang [1 ]
Liu, Yunyun [1 ]
Lv, Xin [1 ]
Oian, Weixing [1 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310028, Zhejiang, Peoples R China
关键词
D O I
10.1021/ol801444p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2, 3-Dihydro-1,4-benzodioxins can be prepared in a tandem one-pot procedure by reaction of o-iodophenols with epoxides catalyzed by Cu2O/1,10-phenanthroline/Cs2CO3 system. The reaction is suggested to occur via a novel ring-opening/coupling mechanism, giving moderate to good yields. Moreover, both aryl and aliphatic epoxides are tolerated under these conditions.
引用
收藏
页码:3899 / 3902
页数:4
相关论文
共 47 条
[1]   Perspectives on 1,4-benzodioxins, 1,4-benzoxazines and their 2,3-dihydro derivatives [J].
Achari, B ;
Mandal, SB ;
Dutta, PK ;
Chowdhury, C .
SYNLETT, 2004, (14) :2449-2467
[2]   REACTIONS OF TETRACHLORO ORTHO BENZOQUINONE AND TETRABROMO ORTHO BENZOQUINONE WITH ACYCLIC DIENES [J].
ANSELL, MF ;
LESLIE, VJ .
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (08) :1423-&
[3]   Copper in cross-coupling reactions - The post-Ullmann chemistry [J].
Beletskaya, IP ;
Cheprakov, AV .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364
[4]   SYNTHESIS OF POLYETHER CARBOXYLIC-ACIDS WITH A BENZODIOXINIC SUBUNIT [J].
BOSSERAY, P ;
GUILLAUMET, G ;
COUDERT, G ;
WASSERMANN, H .
TETRAHEDRON LETTERS, 1989, 30 (11) :1387-1390
[5]   2-aryl and 2-heteroaryl indoles from 1-alkynes and o-lodotrifluoroacetanilide through a domino copper-catalyzed coupling-cyclization process [J].
Cacchi, S ;
Fabrizi, G ;
Parisi, LM .
ORGANIC LETTERS, 2003, 5 (21) :3843-3846
[6]   Geometrically specific hydrogen transfer in the reaction of terminally alkyl-substituted 1,3-dienes with 1,4-quinones [J].
Cameron, DW ;
Heisey, RM .
AUSTRALIAN JOURNAL OF CHEMISTRY, 2000, 53 (02) :109-121
[7]   Elaboration of 2-(trifluoromethyl)indoles via a cascade coupling/condensation/deacylation process [J].
Chen, Yu ;
Wang, Yuji ;
Sun, Zheming ;
Ma, Dawei .
ORGANIC LETTERS, 2008, 10 (04) :625-628
[8]   Four novel lignans from Rodgersia podophylla [J].
Chin, YW ;
Kim, JW .
TETRAHEDRON LETTERS, 2004, 45 (02) :339-341
[9]   PURPURENOL, A HIGHLY OXYGENATED COUMARIN FROM PTEROCAULON-PURPURASCENS [J].
DEBENEDETTI, SL ;
NADINIC, EL ;
COUSSIO, JD ;
DEKIMPE, N ;
FENEAUDUPONT, J ;
DECLERCO, JP .
PHYTOCHEMISTRY, 1991, 30 (08) :2757-2758
[10]   Synthesis of enamines, enol ethers and related compounds by cross-coupling reactions [J].
Dehli, JR ;
Legros, J ;
Bolm, C .
CHEMICAL COMMUNICATIONS, 2005, (08) :973-986