A new consecutive three-component oxazole synthesis by an amidation-coupling-cycloisomerization (ACCI) sequence

被引:106
作者
Merkul, Eugen [1 ]
Mueller, Thomas J. J. [1 ]
机构
[1] Univ Heidelberg, Inst Organ Chem, D-69120 Heidelberg, Germany
关键词
D O I
10.1039/b610839c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A novel consecutive three-component synthesis of 1-(hetero)aryl- 2-(2-(hetero)aryl-oxazol-5-yl) ethanones starting from propargyl amine and acid chlorides, both for amidation and cross-coupling, is based upon an amidation-coupling-cycloisomerization (ACCI) sequence.
引用
收藏
页码:4817 / 4819
页数:3
相关论文
共 35 条
[1]  
Boyd G. V., 2002, SCI SYNTHESIS, V11, P383
[2]  
BROWN WK, 1971, Patent No. 3574228
[3]   Room temperature palladium catalysed coupling of acyl chlorides with terminal alkynes [J].
Cox, RJ ;
Ritson, DJ ;
Dane, TA ;
Berge, J ;
Charmant, JPH ;
Kantacha, A .
CHEMICAL COMMUNICATIONS, 2005, (08) :1037-1039
[4]  
COX RJ, 2005, J ORGANOMET CHEM, P1037
[5]   Biotransformation reactions of five-membered aromatic heterocyclic rings [J].
Dalvie, DK ;
Kalgutkar, AS ;
Khojasteh-Bakht, SC ;
Obach, RS ;
O'Donnell, JP .
CHEMICAL RESEARCH IN TOXICOLOGY, 2002, 15 (03) :269-299
[6]   AN EFFICIENT SYNTHESIS OF ETHYL 5-OXAZOLEACETATES [J].
DOW, RL .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (01) :386-388
[7]  
Hartner F. W., 1996, COMPREHENSIVE HETERO, P261
[8]   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
[9]  
JACOBS HM, 1989, ALKALOIDS, V35, P259
[10]   Muscarine, imidazole, oxazole, and thiazole alkaloids [J].
Jin, Z .
NATURAL PRODUCT REPORTS, 2003, 20 (06) :584-605