A NOVEL CYCLODEHYDRATION REACTION OF HYDROXY-PHENOLS USING IMIDATE ESTERS AS LEAVING GROUPS

被引:30
作者
PROCOPIOU, PA [1 ]
BRODIE, AC [1 ]
DEAL, MJ [1 ]
HAYMAN, DF [1 ]
机构
[1] GLAXO GRP RES LTD,DEPT PROC RES,GREENFORD UB6 0HE,MIDDX,ENGLAND
关键词
D O I
10.1016/S0040-4039(00)60159-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A mild, efficient and stereospecific intramolecular method for converting hydroxy-phenols into benzodioxans, dihydrobenzopyrans and dihydrobenzofurans via imidate esters, and suitable for large scale operation is described.
引用
收藏
页码:7483 / 7486
页数:4
相关论文
共 11 条
[1]   SYNTHESIS OF BENZOPYRAN PROSTAGLANDINS, POTENT STABLE PROSTACYCLIN ANALOGS, VIA AN INTRAMOLECULAR MITSUNOBU REACTION [J].
ARISTOFF, PA ;
HARRISON, AW ;
HUBER, AM .
TETRAHEDRON LETTERS, 1984, 25 (36) :3955-3958
[2]   A NEW METHOD FOR THE PREPARATION OF TERTIARY BUTYL ETHERS AND ESTERS [J].
ARMSTRONG, A ;
BRACKENRIDGE, I ;
JACKSON, RFW ;
KIRK, JM .
TETRAHEDRON LETTERS, 1988, 29 (20) :2483-2486
[3]   TRIPHENYLPHOSPHINE-TETRACHLOROMETHANE PROMOTED CHLORINATION AND CYCLODEHYDRATION OF SIMPLE DIOLS [J].
BARRY, CN ;
EVANS, SA .
JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (16) :3361-3364
[4]   THE PHARMACOLOGY OF FLUPAROXAN - A SELECTIVE ALPHA-2-ADRENOCEPTOR ANTAGONIST [J].
HALLIDAY, CA ;
JONES, BJ ;
SKINGLE, M ;
WALSH, DM ;
WISE, H ;
TYERS, MB .
BRITISH JOURNAL OF PHARMACOLOGY, 1991, 102 (04) :887-895
[5]   BENZYL TRICHLOROACETIMIDATE, A VERSATILE REAGENT FOR ACID-CATALYZED BENZYLATION OF HYDROXY-GROUPS [J].
IVERSEN, T ;
BUNDLE, DR .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (23) :1240-1241
[6]  
KITCHIN J, UNPUB BIOORG MED CHE
[7]   STEROIDS .10. CONVENIENT SYNTHESIS OF ALKYL ARYL ETHERS [J].
MANHAS, MS ;
HOFFMAN, WH ;
LAL, B ;
BOSE, AK .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1975, (05) :461-463
[8]   PREPARATION AND REACTIONS OF SULFONIC ESTERS .4. PREPARATION OF CYCLIC ETHERS [J].
REYNOLDS, DD ;
KENYON, WO .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1950, 72 (04) :1593-1596
[9]   THE CHEMISTRY OF IMIDATES [J].
ROGER, R ;
NEILSON, DG .
CHEMICAL REVIEWS, 1961, 61 (02) :179-211
[10]   ACID-CATALYZED BENZYLATION AND ALLYLATION BY ALKYL TRICHLOROACETIMIDATES [J].
WESSEL, HP ;
IVERSEN, T ;
BUNDLE, DR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (11) :2247-2250