A chemoselective microwave-assisted one-pot cross-Stille reaction of benzylic halides with 2(1H)-pyrazinones using simultaneous cooling

被引:24
作者
Appukkuttan, Prasad
Husain, Mofazzal
Gupta, Rajinder K.
Parmar, Virinder S.
Van der Eycken, Erik
机构
[1] Univ Louvain, Dept Chem, B-3001 Louvain, Belgium
[2] Univ Delhi, Dept Chem, Bioorgan Lab, Delhi 100007, India
[3] GGSIP Univ, Sch Biotechnol, Delhi 100006, India
关键词
microwave; 2(1H)-pyrazinone; Stille; cross-coupling; simultaneous cooling;
D O I
10.1055/s-2006-941607
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
This manuscript reports the chemoselective one-pot cross-Stille coupling of benzylic halides with 3,5-dichloro-2(1H)-pyrazinones, which avoids the purification and handling of toxic stannylated intermediates. Significant improvements in yields were established when microwave irradiation was performed with simultaneous cooling.
引用
收藏
页码:1491 / 1496
页数:6
相关论文
共 26 条
  • [1] Suzuki coupling of aryl chlorides with phenylboronic acid in water, using microwave heating with simultaneous cooling
    Arvela, RK
    Leadbeater, NE
    [J]. ORGANIC LETTERS, 2005, 7 (11) : 2101 - 2104
  • [2] Orthopalladated and -platinated bulky triarylphosphite complexes: Synthesis, reactivity and application as high-activity catalysts for Suzuki and Stille coupling reactions
    Bedford, RB
    Hazlewood, SL
    Limmert, ME
    Albisson, DA
    Draper, SM
    Scully, PN
    Coles, SJ
    Hursthouse, MB
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2003, 9 (14) : 3216 - 3227
  • [3] Palladium-catalyzed borylation of phenyl bromides and application in one-pot Suzuki-Miyaura biphenyl synthesis
    Broutin, PE
    Cerna, I
    Campaniello, M
    Leroux, F
    Colobert, F
    [J]. ORGANIC LETTERS, 2004, 6 (24) : 4419 - 4422
  • [4] Iron-catalyzed homo-coupling of simple and functionalized arylmagnesium reagents
    Cahiez, G
    Chaboche, C
    Mahuteau-Betzer, F
    Ahr, M
    [J]. ORGANIC LETTERS, 2005, 7 (10) : 1943 - 1946
  • [5] Rapid synthesis of α-ketoamides using microwave irradiation-simultaneous cooling method
    Chen, JJ
    Deshpande, SV
    [J]. TETRAHEDRON LETTERS, 2003, 44 (49) : 8873 - 8876
  • [6] Córsico EF, 2000, SYNLETT, P230
  • [7] Design and synthesis of novel type VI-like β-turn mimetics.: Diversity at the i+1 and the i+2 position
    De Borggraeve, WM
    Verbist, BMP
    Rombouts, FJR
    Pawar, VG
    Smets, WJ
    Kamoune, L
    Alen, J
    Van der Eycken, EV
    Compernolle, F
    Hoornaert, GJ
    [J]. TETRAHEDRON, 2004, 60 (50) : 11597 - 11612
  • [8] Synthesis of a conformationally restricted dipeptide analogue and its evaluation as a β-turn mimic
    De Borggraeve, WM
    Rombouts, FJR
    Van der Eycken, EV
    Toppet, SM
    Hoornaert, GJ
    [J]. TETRAHEDRON LETTERS, 2001, 42 (33) : 5693 - 5695
  • [9] New perspectives in the cross-coupling reactions of organostannanes
    Farina, V
    [J]. PURE AND APPLIED CHEMISTRY, 1996, 68 (01) : 73 - 78
  • [10] Design, synthesis, and SAR of a novel pyrazinone series with non-nucleoside HIV-1 reverse transcriptase inhibitory activity
    Heeres, J
    de Jonge, MR
    Koymans, LMH
    Daeyaert, FFD
    Vinkers, M
    Van Aken, KJA
    Arnold, E
    Das, K
    Kilonda, A
    Hoornaert, GJ
    Compernolle, F
    Cegla, M
    Azzam, RA
    Andries, K
    de Béthune, MP
    Azijn, H
    Pauwels, R
    Lewi, PJ
    Janssen, PAJ
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (06) : 1910 - 1918