Solution-phase parallel oxazole synthesis with TosMIC

被引：40

作者：

Kulkarni, BA ^{[1
]}

Ganesan, A ^{[1
]}

机构：

[1] Natl Univ Singapore, Inst Mol & Cell Biol, Singapore 117609, Singapore

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 30期

关键词：

supported reagents reactions; combinatorial chemistry; isocyanides; oxazoles;

D O I：

10.1016/S0040-4039(99)01050-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A quaternary ammonium hydroxide ion exchange resin catalyzes the reaction of p-tolylsulfonylmethyl isocyanide (TosMIC) with aromatic aldehydes to give 5-aryloxazoles. The base and the p-tolylsulfinic acid byproduct are removed by simple filtration, resulting in oxazoles in high yield and purity. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：5637 / 5638

页数：2

共 13 条

[1] Application of palladium(0)-catalyzed processes to the synthesis of oxazole-containing partial ergot alkaloids [J].

Anderson, BA ;

Becke, LM ;

Booher, RN ;

Flaugh, ME ;

Harn, NK ;

Kress, TJ ;

Varie, DL ;

Wepsiec, JP .

JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (25) :8634-8639

[2] 2-METALATED OXAZOLES - PKA DEPENDENT DEUTERATIONS, NMR-STUDIES AND PALLADIUM-CATALYZED COUPLINGS [J].

CROWE, E ;

HOSSNER, F ;

HUGHES, MJ .

TETRAHEDRON, 1995, 51 (32) :8889-8900

[3]

CROZET MP, 1993, HETEROCYCLES, V36, P45

[4]

Gayo LM, 1998, BIOTECHNOL BIOENG, V61, P95, DOI 10.1002/(SICI)1097-0290(199821)61:2<95::AID-BIT4>3.3.CO

[5]

2-0

[6]

HORNE DA, 1994, HETEROCYCLES, V39, P139

[7] Solution-phase combinatorial synthesis of 4-hydroxyquinolin-2(1H)-ones [J].

Kulkarni, BA ;

Ganesan, A .

CHEMICAL COMMUNICATIONS, 1998, (07) :785-786

[8] Ion-exchange resins for combinatorial synthesis: 2,4-pyrrolidinediones by Dieckmann condensation [J].

Kulkarni, BA ;

Ganesan, A .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1997, 36 (22) :2454-2455

[9] p-tolylsulfonylmethyl isocyanide (TosMIC) - a versatile formaldehyde equivalent with reversed polarity [J].

Lamberth, C .

JOURNAL FUR PRAKTISCHE CHEMIE-CHEMIKER-ZEITUNG, 1998, 340 (05) :483-485

[10]

OUSSAID B, 1993, B SOC CHIM FR, V130, P86

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