Solid phase synthesis of 3,5-disubstituted oxazolidin-2-ones

被引：12
|
作者：
Rastogi, SK
Srivastava, GK
Singh, SK
Grover, RK
Roy, R
Kundu, B [1 ]
机构：
[1] Cent Drug Res Inst, Div Med Chem, Lucknow 226001, Uttar Pradesh, India
[2] Cent Drug Res Inst, Div RSIC, NMR Lab, Lucknow 226001, Uttar Pradesh, India
来源：
TETRAHEDRON LETTERS | 2002年 / 43卷 / 46期
基金：
澳大利亚研究理事会;
关键词：
D O I：
10.1016/S0040-4039(02)02009-9
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A versatile method for the solid phase synthesis of oxazolidin-2-ones is described. A resin bound phenolic group was treated with (+/-)-epichlorohydrin followed by opening of the epoxide ring with sodium azide. The resulting 1-azido-3-aryloxypropan-2-ol was treated with p-nitrophenylchloroformate and subsequent Staudinger's cyclization using PPh3 yielded a 5-substituted oxazolidinone. Finally, additional diversity at position 3 was introduced by treating the 5-substituted oxazolidinone with an alkyl halide in the presence of NaH to give the desired compound in high yield and purity. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：8327 / 8330
页数：4
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