Iron Trichloride Catalyzed One-Pot Synthesis of Substituted Oxazoles from Propargylic Acetates and Amides under Microwave Irradiation

被引：6
作者：
Xu, Wen-Wen
Lin, Min [1 ]
Huang, Yang
Chen, Li
Zhan, Zhuang-Ping
机构：
[1] Xiamen Univ, Dept Chem, Coll Chem & Chem Engn, Xiamen 361005, Peoples R China
来源：
LETTERS IN ORGANIC CHEMISTRY | 2009年 / 6卷 / 08期
基金：
中国国家自然科学基金;
关键词：
Iron trichloride; oxazole; microwave irradiation; FECL3-CATALYZED NUCLEOPHILIC-SUBSTITUTION; STRAIGHTFORWARD SYNTHESIS; ASYMMETRIC-SYNTHESIS; EFFICIENT SYNTHESIS; ORGANIC-SYNTHESIS; ALCOHOLS; ISOCYANIDES; CYCLIZATION; ALDEHYDES;
D O I：
10.2174/157017809790442970
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A rapid and efficient procedure under microwave irradiation, using silica gel-supported reagents for the synthesis of substitued oxazoles has been developed through iron trichloride catalyzed propargylation/cycloisomerization tandem reaction of propargylic acetates and amides.
引用
收藏
页码：664 / 668
页数：5
相关论文
共 42 条
[11]   Controlled microwave heating in modern organic synthesis [J].
Kappe, CO .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (46) :6250-6284
[12]   Total synthesis of dimethyl sulfomycinamate [J].
Kelly, TR ;
Lang, FR .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (14) :4623-4633
[13]   One-pot Friedel-Crafts/Robinson-Gabriel synthesis of oxazoles using oxazolone templates [J].
Keni, M ;
Tepe, JJ .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (10) :4211-4213
[14]   TUNGSTEN HEXACHLORIDE CATALYZED DECOMPOSITION OF DIAZO-COMPOUNDS - NOVEL OXAZOLE SYNTHESIS [J].
KITATANI, K ;
HIYAMA, T ;
NOZAKI, H .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1977, 50 (06) :1647-1648
[15]   Zn(OTf)2-catalyzed cyclization of propargyl alcohols with anilines, phenols, and amides for synthesis of indoles, benzofurans, and oxazoles through different annulation mechanisms [J].
Kumar, Manyam Praveen ;
Liu, Rai-Shung .
JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (13) :4951-4955
[16]   Synthetic studies of the formation of oxazoles and isoxazoles from N-acetoacetyl derivatives:: Scope and limitations [J].
Lautens, M ;
Roy, A .
ORGANIC LETTERS, 2000, 2 (04) :555-557
[17]   Efficient synthesis of multi-substituted oxazoles under solvent-free microwave irradiation [J].
Lee, JC ;
Choi, HJ ;
Lee, YC .
TETRAHEDRON LETTERS, 2003, 44 (01) :123-125
[18]   Mercury(II) p-toluenesulfonate mediated synthesis of oxazoles under microwave irradiation [J].
Lee, JC ;
Song, IG .
TETRAHEDRON LETTERS, 2000, 41 (31) :5891-5894
[19]   Microwave assisted organic synthesis -: a review [J].
Lidström, P ;
Tierney, J ;
Wathey, B ;
Westman, J .
TETRAHEDRON, 2001, 57 (45) :9225-9283
[20]   [(NHC)AuI]-catalyzed formation of conjugated enones and enals:: An experimental and computational study [J].
Marion, Nicolas ;
Carlqvist, Peter ;
Gealageas, Ronan ;
de Fremont, Pierre ;
Maseras, Feliu ;
Nolan, Steven P. .
CHEMISTRY-A EUROPEAN JOURNAL, 2007, 13 (22) :6437-6451
12345