Efficient preparation of 4-iodofuran-2(5H)-ones by iodolactonisation of 2,3-allenoates with I2

被引:75
作者
Fu, CL [1 ]
Ma, SM
机构
[1] Zhejiang Univ, Dept Chem, Lab Mol Recognit & Synth, Hangzhou 310027, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
关键词
allenes; cyclisation; esters; iodine; lactones;
D O I
10.1002/ejoc.200500296
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
4 -Iodofuran-2(5H)-ones were prepared, in moderate to high yields, by the facile iodolactonisation of ethyl 2,3-allenoates with I2 in aqueous MeCN by the direct participation of the carbonyl oxygen atom in the regioselective electrophilic addition of the allene moiety. (c) Wiley-VCH Verlag GmbH & Co, KGaA, 69451 Weinheim, Germany, 2005.
引用
收藏
页码:3942 / 3945
页数:4
相关论文
共 34 条
[1]   Pauson-Khand reaction with allenic compounds .2. Reactivity of functionalized allenes. [J].
Ahmar, M ;
Chabanis, O ;
Gauthier, J ;
Cazes, B .
TETRAHEDRON LETTERS, 1997, 38 (30) :5277-5280
[2]  
Brima T. S., 1990, US Pat, Patent No. [4968817, 4968817A]
[3]   Fissohamione, a novel furanone from Fissistigma oldhamii [J].
Chia, YC ;
Chang, FR ;
Wu, YC .
TETRAHEDRON LETTERS, 1999, 40 (42) :7513-7514
[4]   Meliacin butenolides from Trichilia estipulata [J].
Cortez, DAG ;
Fernandes, JB ;
Vieria, PC ;
Da Silva, MFGF ;
Ferreira, AG ;
Cass, QB ;
Pirani, JR .
PHYTOCHEMISTRY, 1998, 49 (08) :2493-2496
[5]   CYCLOHEXYL BUTENOLIDE GLUCOSIDES FROM EPACRIDACEAE [J].
DAMTOFT, S ;
JENSEN, SR .
PHYTOCHEMISTRY, 1995, 40 (01) :157-159
[6]  
Gauthier J.Y., 1995, PCT Int. Appl. WO 95 00,501, Patent No. [9500501, 95 00,501]
[7]   SYNTHESIS OF ALPHA,BETA-UNSATURATED BUTENOLIDES FROM ALLENIC ACIDS [J].
GILL, GB ;
IDRIS, MSH .
TETRAHEDRON LETTERS, 1985, 26 (39) :4811-4814
[8]  
LANG R, 1984, ORG SYNTH, P202
[9]   SIMPLE SYNTHESIS OF ALKYL ALLENECARBOXYLATES (ALLENIC ESTERS) BY THE WITTIG-REACTION [J].
LANG, RW ;
HANSEN, HJ .
HELVETICA CHIMICA ACTA, 1980, 63 (02) :438-455
[10]   MERCURY IN ORGANIC-CHEMISTRY .12. SYNTHESIS OF BETA-CHLORO-DELTA-ALPHA-DELTA-BETA-BUTENOLIDES VIA MERCURATION-CARBONYLATION OF PROPARGYLIC ALCOHOLS [J].
LAROCK, RC ;
RIEFLING, B ;
FELLOWS, CA .
JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (01) :131-137