High-throughput synthesis of N3-acylated dihydropyrimidines combining microwave-assisted synthesis and scavenging techniques

被引：138
作者：
Dallinger, D [1 ]
Gorobets, NY [1 ]
Kappe, CO [1 ]
机构：
[1] Karl Franzens Univ Graz, Inst Chem, A-8010 Graz, Austria
来源：
ORGANIC LETTERS | 2003年 / 5卷 / 08期
关键词：
D O I：
10.1021/ol034085v
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The solution-phase synthesis of N3-acylated dihydropyrimidines was achieved utilizing microwave flash heating both in the synthesis (acylation) and purification (scavenging) steps. Quenching times for excess anhydrides using polystyrene or silica-supported diamine sequestration reagents were reduced from several hours to minutes utilizing microwave irradiation. The use of water as sequestration agent, coupled with an efficient solid-phase extraction workup technique allowed the rapid generation of a 20-member library of N3-acylated dihydropyrimidines.
引用
收藏
页码：1205 / 1208
页数：4
相关论文
共 31 条
  • [1] Microwave-assisted solid-phase synthesis (MASS) of 2,6,9-trisubstituted purines
    Austin, RE
    Okonya, JF
    Bond, DRS
    Al-Obeidi, F
    [J]. TETRAHEDRON LETTERS, 2002, 43 (35) : 6169 - 6171
  • [2] A concise synthesis of carpanone using solid-supported reagents and scavengers
    Baxendale, IR
    Lee, AL
    Ley, SV
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2002, (16): : 1850 - 1857
  • [3] Rapid microwave-assisted liquid-phase combinatorial synthesis of 2-(arylamino)benzimidazoles
    Bendale, PM
    Sun, CM
    [J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2002, 4 (04): : 359 - 361
  • [4] Solid-supported reagent strategies for rapid purification of combinatorial synthesis products
    Booth, RJ
    Hodges, JC
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1999, 32 (01) : 18 - 26
  • [5] Microwave parallel library generation:: Comparison of a conventional- and microwave-generated substituted 4(5)-sulfanyl-1H-imidazole library
    Coleman, CM
    MacElroy, JMD
    Gallagher, JF
    O'Shea, DF
    [J]. JOURNAL OF COMBINATORIAL CHEMISTRY, 2002, 4 (01): : 87 - 93
  • [6] Microwave-accelerated O-alkylation of carboxylic acids with O-alkylisoureas
    Crosignani, S
    White, PD
    Linclau, B
    [J]. ORGANIC LETTERS, 2002, 4 (17) : 2961 - 2963
  • [7] Eames J, 2001, EUR J ORG CHEM, V2001, P1213
  • [8] Erdélyi M, 2002, SYNTHESIS-STUTTGART, P1592
  • [9] Microwave-assisted solid-phase synthesis of 5-carboxamido-N-acetyltryptamine derivatives
    Fînaru, A
    Berthault, A
    Besson, T
    Guillaumet, G
    Berteina-Raboin, S
    [J]. ORGANIC LETTERS, 2002, 4 (16) : 2613 - 2615
  • [10] KAPPE CO, 1993, TETRAHEDRON, V49, P6937
1234