Reaction of 2-alkylidenetetrahydrofurans with boron tribromide: Chemo- and regioselective synthesis of 6-bromo-3-oxoalkanoates by application of a 'cyclization-ring-opening' strategy

被引:10
作者
Bellur, E [1 ]
Langer, P [1 ]
机构
[1] Ernst Moritz Arndt Univ Greifswald, Inst Chem & Biochem, D-17487 Greifswald, Germany
关键词
boron tribromide; domino reactions; nucleophilic substitution; halogenation; tetrahydrofurans;
D O I
10.1055/s-2004-830893
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
6-Bromo-3-oxoalkanoates, benzofurans and 1,7-dibromoheptan-4-ones were chemo- and regioselectively prepared by reaction of 2-alkylidenetetrahydrofurans with boron tribromide.
引用
收藏
页码:2172 / 2174
页数:3
相关论文
共 27 条
[1]   UPSILON-TRIAZOLINES .19. THIOCINO[4,5-D]-1,2,3-TRIAZOLE AND THIOCINO[4,5-D]ISOXAZOLE DERIVATIVES [J].
ALMIRANTE, N ;
FORTI, L .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1984, 21 (04) :1121-1123
[2]  
BELLUR E, SYNLETT
[3]   CLEAVAGE OF ETHERS [J].
BHATT, MV ;
KULKARNI, SU .
SYNTHESIS-STUTTGART, 1983, (04) :249-282
[4]   Hydrogenation and hydrogenolysis of furan derivatives [J].
Burdick, HE ;
Adkins, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1934, 56 :438-442
[5]   Synthesis and preliminary characterization of a novel antiarrhythmic compound (KB130015) with an improved toxicity profile compared with amiodarone [J].
Carlsson, B ;
Singh, BN ;
Temciuc, M ;
Nilsson, S ;
Li, YL ;
Mellin, C ;
Malm, J .
JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (03) :623-630
[6]   SYNTHESIS OF SINGLE ISOMERS (E OR Z) OF PROTECTED GAMMA,DELTA-UNSATURATED KETONES BY THE HORNER-WITTIG REACTION [J].
CORNISH, CA ;
WARREN, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (12) :2585-2598
[7]   The structure of C7H12O2 from the hydrogenation of furylacrolein [J].
Farlow, M ;
Burdick, HE ;
Adkins, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1934, 56 (07) :2498-2499
[8]  
FITTIT G, 1892, LIEBIGS ANN CHEM, V267, P192
[9]   TWOFOLD TERMINAL ALKYLATIONS OF DISODIO BETA-DIKETONES WITH METHYLENE HALIDES TO FORM BIS-BETA-DIKETONES [J].
HAMPTON, KG ;
LIGHT, RJ ;
HAUSER, CR .
JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (05) :1413-&
[10]  
KULKARNI SU, 1982, HETEROCYCLES, V18, P163