HIGHLY CHEMOSELECTIVE ACYLATION OF SUBSTITUTED AMINOPHENOLS WITH 3-(TRIMETHYLACETYL)-1,3-THIAZOLIDINE-2-THIONE

被引：10

作者：

DAI, WM

CHEUNG, YK

TANG, KW

CHOI, PY

CHUNG, SL

机构：

[1] Department of Chemistry, The Hong Kong University of Science and Technology Clear Water Bay, Kowloon

来源：

TETRAHEDRON | 1995年 / 51卷 / 45期

关键词：

D O I：

10.1016/0040-4020(95)00783-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A general procedure for chemoselective acylation of substituted aminophenols has been developed. The N-acylated products 7 and 10a-h were prepared by treating me aminophenols with 3-(trimethylacetyl)-1,3-thiazolidine-2-thione (1) in refluxing THF in 70-100% yield. The eaters 8 and 13d,bj of 3- and 4-amino phenols could be obtained in 70-94% yield by treating with NaH and 1.

引用

页码：12263 / 12276

页数：14

共 24 条

[1] ARNAUD N, 1994, SYNLETT, P553
[2] CHUNGSHI L, 1981, TETRAHEDRON LETT, V22, P3467
[3] ORTHO FUNCTIONALIZATION OF AROMATIC-AMINES - ORTHO LITHIATION OF N-PIVALOYLANILINES
FUHRER, W
GSCHWEND, HW
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (07) : 1133 - 1136
[4] A NEW EFFICIENT AMINOLYSIS AND ITS APPLICATION TO SYNTHESIS OF MACROLACTAM ALKALOIDS
FUJITA, E
[J]. PURE AND APPLIED CHEMISTRY, 1981, 53 (06) : 1141 - 1154
[5] GREEN TW, 1991, PROTECTIVE GROUPS OR
[6] PARTIAL REDUCTION OF CARBOXYLIC-ACIDS TO ALDEHYDES VIA 3-ACYLTHIAZOLIDINE-2-THIONES WITH DIISOBUTYLALUMINUM HYDRIDE
IZAWA, T
MUKAIYAMA, T
[J]. CHEMISTRY LETTERS, 1977, (12) : 1443 - 1446
[7] IZAWA T, 1979, B CHEM SOC JPN, V53, P555
[8] Kocienski P.J., 1994, PROTECTING GROUPS
[9] KURAMOTO T, 1981, CHEM PHARM BULL, V29, P1136
[10] A NEW DESIGN FOR CHIRAL INDUCTION - A HIGHLY REGIOSELECTIVE DIFFERENTIATION BETWEEN 2 IDENTICAL GROUPS IN AN ACYCLIC COMPOUND HAVING A PROCHIRAL CENTER
NAGAO, Y
IKEDA, T
YAGI, M
FUJITA, E
SHIRO, M
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (07) : 2079 - 2081

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