Silver-catalyzed preparation of oxazolines from N-propargylamides

被引：46

作者：

Harmata, Michael ^{[1
]}

Huang, Chaofeng ^{[1
]}

机构：

[1] Univ Missouri, Dept Chem, Columbia, MO 65211 USA

来源：

SYNLETT | 2008年 / 09期

关键词：

N-propargylamides; silver; oxazolines; catalysis;

D O I：

10.1055/s-2008-1078405

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of N-propargylamides with 5 mol% of silver hexafluoroantimonate results in the rapid formation of oxazolines in essentially quantitative yield.

引用

页码：1399 / 1401

页数：3

共 19 条

[1] Heterocyclic derivative syntheses by palladium-catalyzed oxidative cyclization -: Alkoxycarbonylation of substituted γ-oxoalkynes [J].

Bacchi, A ;

Costa, M ;

Della Cà, N ;

Gabriele, B ;

Salerno, G ;

Cassoni, S .

JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (13) :4971-4979

[2] Efficient and general synthesis of 5-(alkoxycarbonyl)methylene-3-oxazolines by palladium-catalyzed oxidative carbonylation of prop-2-ynylamides [J].

Bacchi, A ;

Costa, M ;

Gabriele, B ;

Pelizzi, G ;

Salerno, G .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (13) :4450-4457

[3] Gold(I)-catalyzed formation of 5-methylene-1,3-oxazolidin-2-ones [J].

Buzas, Andrea ;

Gagosz, Fabien .

SYNLETT, 2006, (17) :2727-2730

[4] Multi-component syntheses of heterocycles by transition-metal catalysis [J].

D'Souza, Daniel M. ;

Mueller, Thomas J. J. .

CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) :1095-1108

[5] ACETYLENIC AMINES .12. SOME NEW REACTIONS OF ACYLAMINOACETYLENES [J].

EASTON, NR ;

CASSADY, DR ;

DILLARD, RD .

JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (09) :3084-&

[6] Silver-catalyzed rearrangement of propargylic sulfinates to allenic sulfones [J].

Harmata, Michael ;

Huang, Chaofeng .

ADVANCED SYNTHESIS & CATALYSIS, 2008, 350 (7-8) :972-974

[7] Gold catalysis: Alkylideneoxazolines and -oxazoles from intramolecular hydroamination of an alkyne by a trichloroacetimidate [J].

Hashmi, A. Stephen K. ;

Rudolph, Matthias ;

Schymura, Stefan ;

Visus, Jorge ;

Frey, Wolfgang .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (21) :4905-4909

[8] Gold catalysis [J].

Hashmi, A. Stephen K. ;

Hutchings, Graham J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (47) :7896-7936

[9] Gold catalysis:: Mild conditions for the synthesis of oxazoles from N-propargylcarboxamides and mechanistic aspects [J].

Hashmi, ASK ;

Weyrauch, JP ;

Frey, W ;

Bats, JW .

ORGANIC LETTERS, 2004, 6 (23) :4391-4394

[10] Synthesis and identification of novel 11β-aryl-4′,5′-dihydrospiro[estra-4,9-diene-17β,4′-oxazole] analogs with dissociated antiprogesterone activities [J].

Jin, Chunyang ;

Manikumar, G. ;

Kepler, John A. ;

Cook, C. Edgar ;

Allan, George F. ;

Kiddoe, Margaret ;

Bhattacharjee, Sheela ;

Linton, Olivia ;

Lundeen, Scott G. ;

Sui, Zhihua .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2007, 17 (21) :5754-5757

← 1 2 →