Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2010(1): 136-140
DOI: 10.1055/s-0029-1217065
DOI: 10.1055/s-0029-1217065
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Straightforward Functionalization of 3,5-Dichloro-2-pyrazinones under Simultaneous Microwave and Ultrasound Irradiation
Further Information
Received
6 July 2009
Publication Date:
26 October 2009 (online)
Publication History
Publication Date:
26 October 2009 (online)
Abstract
Heck reactions and Suzuki-Miyaura cross-couplings with relatively poorly reactive 3,5-dichloro-2-pyrazinones were studied at the same temperature under conventional heating, dielectric heating (MW) and simultaneous MW/US irradiation. This comparative study showed a synergic effect of combined MW and US irradiation resulting in a much higher reaction yield, at the same time avoiding side reactions and partial degradation that is otherwise observed under conventional heating.
Key words
pyrazinones - ultrasound - microwaves - simultaneous irradiation - Heck reaction - Suzuki cross-coupling
- 1
Burke MD.Berger EM.Schreiber SL. Science 2003, 302: 613 - 2
Polshettiwar V.Varma RS. Acc. Chem. Res. 2008, 41: 629 -
3a
Roberts BA.Strauss CR. Acc. Chem. Res. 2005, 38: 653 -
3b
Kappe CO. Chem. Soc. Rev. 2008, 37: 1127 -
3c
Caddick S.Fitzmaurice R. Tetrahedron 2009, 65: 3325 - 4
Cravotto G.Cintas P. Chem. Soc. Rev. 2006, 35: 180 - 5
Ruecroft G.Hipkiss D.Ly T.Maxted N.Cains PW. Org. Process Res. Dev. 2005, 9: 923 - 6
Cravotto G.Cintas P. Chem. Eur. J. 2007, 13: 1903 - 7
Barge A.Tagliapietra S.Tei L.Cintas P.Cravotto G. Curr. Org. Chem. 2008, 12: 1588 - 8
Van der Eycken E.Kappe CO. In Topics in Heterocyclic Chemistry Vol. 1: Springer; Berlin: 2006. p.267 - 9
De Borggraeve WM.Rombouts FJR.Van der Eycken EV.Toppet SM.Hoornaert GJ. Tetrahedron Lett. 2001, 42: 5693 - 10
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 Bethune MP.Azijn H.Pauwels R.Lewi PJ.Janssen PAJ. J. Med. Chem. 2005, 48: 1901 - 11
Jinsmaa Y.Miyazaki A.Fujita Y.Li T.Fujisawa Y.Shiotani K.Tsuda Y.Yokoi T.Ambo A.Sasaki Y.Bryant SD.Lazarus LH.Okada Y. J. Med. Chem. 2004, 47: 2599 - 12
Parlow JJ.Kurumbail RG.Stegeman RA.Stevens AM.Stallings WC.South MS. J. Med. Chem. 2003, 46: 4696 - 13
Pawar VG.De Borggraeve WM. Synthesis 2006, 2799 - 14
Kaval N.Bisztray K.Dehaen W.Kappe CO.Van der Eycken E. Mol. Diversity 2003, 7: 125 - 15
Kaval N.Singh BK.Ermolat’ev DS.Claerhout S.Van der Eycken J.Van der Eycken E. J. Comb. Chem. 2007, 9: 446 - 16
Kaval N.Van der Eycken J.Caroen J.Dehaen W.Strohmeier GA.Kappe CO.Van der Eycken E. J. Comb. Chem. 2003, 5: 560 - 17
Azzam R.De Borggraeve WM.Compernolle F.Hoornaert GJ. Tetrahedron Lett. 2003, 61: 3953 - 18
Appukkuttan P.Van der Eycken E. Eur. J. Org. Chem. 2008, 1133 - 19
Mehta VP.Sharma A.Van der Eycken E. Org. Lett. 2008, 10: 1147 - 20
Cravotto G.Palmisano G.Tollari S.Nano GM.Penoni A. Ultrason. Sonochem. 2005, 12: 91 - 21
Cravotto G.Beggiato M.Palmisano G.Penoni A.Lévêque JM.Bonrath W. Tetrahedron Lett. 2005, 46: 2267 - 22
Palmisano G.Bonrath W.Boffa L.Garella D.Barge A.Cravotto G. Adv. Synth. Catal. 2007, 349: 2338 - 23
Palmisano G.Tagliapietra S.Barge A.Binello A.Cravotto G. Synlett 2007, 13: 2041 - 24
Cravotto G.Garella D.Calcio Gaudino E.Lévêque J.-M. Chem. Today 2008, 26: 39 - 25
Schröter S.Stock C.Bach T. Tetrahedron 2005, 61: 2245 - 26
Singh BK.Mehta VP.Parmar VS.Van der Eycken E. Org. Biomol. Chem. 2007, 5: 2962