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

相关论文

共 16 条

[1] A novel isoxazole-based scaffold for combinatorial chemistry [J].

Batra, S ;

Rastogi, SK ;

Kundu, B ;

Patra, A ;

Bhaduri, AP .

TETRAHEDRON LETTERS, 2000, 41 (31) :5971-5974

[2] A novel diterpenoid lactone-based scaffold for the generation of combinatorial libraries [J].

Biabani, MAF ;

Grover, RK ;

Singh, SK ;

Kumar, S ;

Raj, K ;

Roy, R ;

Kundu, B .

TETRAHEDRON LETTERS, 2001, 42 (40) :7119-7121

[3] Recent advances in the preparation of heterocycles on solid support:: A review of the literature [J].

Franzén, RG .

JOURNAL OF COMBINATORIAL CHEMISTRY, 2000, 2 (03) :195-214

[4] CHEMISTRY OF TRICARBONYL HEMIKETALS AND APPLICATION OF EVANS TECHNOLOGY TO THE TOTAL SYNTHESIS OF THE IMMUNOSUPPRESSANT (-)-FK-506 [J].

JONES, TK ;

REAMER, RA ;

DESMOND, R ;

MILLS, SG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (08) :2998-3017

[5] Solid-phase synthesis of quinazolin-4(3H)-ones with three-point diversity [J].

Kesarwani, AP ;

Srivastava, GK ;

Rastogi, SK ;

Kundu, B .

TETRAHEDRON LETTERS, 2002, 43 (32) :5579-5581

[6] Solid phase heterocyclic chemistry [J].

Krchnak, V ;

Holladay, MW .

CHEMICAL REVIEWS, 2002, 102 (01) :61-91

[7] Identification of a potent analogue of nazumamide A through iteration of combinatorial tetrapeptide libraries [J].

Kundu, B ;

Bauser, M ;

Betschinger, J ;

Kraas, W ;

Jung, G .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (13) :1669-1672

[8] Combinatorial approach to lead optimization of a novel hexapeptide with antifungal activity [J].

Kundu, B ;

Rastogi, SK ;

Batra, S ;

Raghuwanshi, SK ;

Shukla, PK .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (16) :1779-1781

[9]

Pathak A, 2002, COMB CHEM HIGH T SCR, V5, P241, DOI 10.2174/1386207024607275

[10] Synthesis of chiral alpha-substituted beta-hydroxy acid derivatives on solid support [J].

Purandare, AV ;

Natarajan, S .

TETRAHEDRON LETTERS, 1997, 38 (51) :8777-8780