Studies on Isocyanides and related compounds:: A facile synthesis of 1,6-dihydro-6-oxopyrazine-2-carboxylic acid derivatives via ugi four-component condensation

被引:1
作者
Faggi, C
García-Valverde, M
Marcaccini, S
Pepino, R
Pozo, MC
机构
[1] Univ Florence, Dipartimento Chim Organ Ugo Schiff, I-50019 Sesto Fiorentino, FI, Italy
[2] Univ Florence, Ctr Interdipartimentale Cristallog, CRIST, I-50019 Sesto Fiorentino, FI, Italy
[3] Univ Burgos, Fac Ciencias, Dept Quim, Burgos 09001, Spain
来源
SYNTHESIS-STUTTGART | 2003年 / 10期
关键词
Ugi reaction; cyclizations; heterocycles; isocyanides; pyrazine ring synthesis;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Ugi four-component condensation (U-4CC) between arylglyoxals 7, amines 6, benzoylformic acid (4) and isocyanides 5 afforded the expected products 8 which were cyclized in a 5+1 fashion with ammonium acetate to give 1,N-disubstituted 4-aryl-1,6-dihydro-6-oxo-5-phenylpyrazine-2-carboxamides 9 in good yields. Evidence for the assigned structures 9 was provided by C-13 NMR spectra and X-ray analysis of 9a.
引用
收藏
页码:1553 / 1558
页数:6
相关论文
共 40 条
[1]   SIR97:: a new tool for crystal structure determination and refinement [J].
Altomare, A ;
Burla, MC ;
Camalli, M ;
Cascarano, GL ;
Giacovazzo, C ;
Guagliardi, A ;
Moliterni, AGG ;
Polidori, G ;
Spagna, R .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1999, 32 :115-119
[2]   Multiple-component condensation strategies for combinatorial library synthesis [J].
Armstrong, RW ;
Combs, AP ;
Tempest, PA ;
Brown, SD ;
Keating, TA .
ACCOUNTS OF CHEMICAL RESEARCH, 1996, 29 (03) :123-131
[3]  
BARLIN GB, 1982, PYRAZINES, P49
[4]   A novel three-component butenolide synthesis [J].
Beck, B ;
Magnin-Lachaux, M ;
Herdtweck, E ;
Dömling, A .
ORGANIC LETTERS, 2001, 3 (18) :2875-2878
[5]  
Bienaymé H, 2000, CHEM-EUR J, V6, P3321, DOI 10.1002/1521-3765(20000915)6:18<3321::AID-CHEM3321>3.0.CO
[6]  
2-A
[7]  
Bossio R, 1997, SYNTHESIS-STUTTGART, P1389
[8]   A facile synthesis of beta-lactams based on the isocyanide chemistry [J].
Bossio, R ;
Marcos, CF ;
Marcaccini, S ;
Pepino, R .
TETRAHEDRON LETTERS, 1997, 38 (14) :2519-2520
[9]  
Bossio R, 1997, HETEROCYCLES, V45, P1589
[10]  
Bossio R, 1999, HETEROCYCLES, V50, P463