THE ACTION OF DIETHYLAMINOSULFUR TRIFLUORIDE (DAST) ON TRANS-4-AMIDO-3-CHROMANOLS - PREPARATION OF CIS-AMIDOALCOHOLS VIA OXAZOLINES

被引：72

作者：

BURRELL, G ^{[1
]}

EVANS, JM ^{[1
]}

JONES, GE ^{[1
]}

STEMP, G ^{[1
]}

机构：

[1] SMITHKLINE BEECHAM PHARMACEUT,MED RES CTR,THE PINNACLES,HARLOW CM19 5AD,ESSEX,ENGLAND

来源：

TETRAHEDRON LETTERS | 1990年 / 31卷 / 25期

关键词：

D O I：

10.1016/S0040-4039(00)94467-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of a variety of trans-4-amido-3-chromanols (3) with DAST gives oxazolines (4) which can be hydrolysed to give the corresponding cis-amido-alcohols (5). Similar treatment of the trans-4-ureido-3-chromanol (8) gave the unexpected 4-fluoro-3-ureidochromanol (9) as the major product. © 1990.

引用

页码：3649 / 3652

页数：4

共 4 条

[1] SYNTHESIS AND ANTIHYPERTENSIVE ACTIVITY OF 4-(CYCLIC AMIDO)-2H-1-BENZOPYRANS
ASHWOOD, VA
BUCKINGHAM, RE
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EVANS, JM
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HAMILTON, TC
NASH, DJ
STEMP, G
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[2] AN UNUSUAL HYDROXYL INVERSION MEDIATED BY DAST
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PINTO, IL
[J]. TETRAHEDRON LETTERS, 1989, 30 (25) : 3349 - 3350
[3] MODERN METHODS FOR THE INTRODUCTION OF FLUORINE INTO ORGANIC-MOLECULES - AN APPROACH TO COMPOUNDS WITH ALTERED CHEMICAL AND BIOLOGICAL-ACTIVITIES
MANN, J
[J]. CHEMICAL SOCIETY REVIEWS, 1987, 16 (04) : 381 - 436
[4] DAST-INDUCED EPIMERIZATION OF A 2-(ACETOXYMETHYL)MYOINOSITOL
YANG, SS
BEATTIE, TR
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (08) : 1718 - 1720

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