Straightforward Functionalization
of 3,5-Dichloro-2-pyrazinones under Simultaneous Microwave
and Ultrasound Irradiation

Davide Garella; Silvia Tagliapietra; Vaibhav P. Mehta; Erik Van der Eycken; Giancarlo Cravotto

doi:10.1055/s-0029-1217065

PAPER

Straightforward Functionalization of 3,5-Dichloro-2-pyrazinones under Simultaneous Microwave and Ultrasound Irradiation

Davide Garella^a, Silvia Tagliapietra^a, Vaibhav P. Mehta^b, Erik Van der Eycken^b, Giancarlo Cravotto*^a
^a Dipartimento di Scienza e Tecnologia del Farmaco, Università degli Studi di Torino, Via P. Giuria 9, 10125 Torino, Italy
Fax: +39(011)6707687; e-Mail: giancarlo.cravotto@unito.it;
^b Laboratory for Organic and Microwave-Assisted Chemistry, Department of Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium

Abstract

Alle Artikel dieser Rubrik

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

Volltext

Referenzen

References

<A NAME="RT13209SS-1">1</A> Burke MD. Berger EM. Schreiber SL. Science 2003, 302: 613

<A NAME="RT13209SS-2">2</A> Polshettiwar V. Varma RS. Acc. Chem. Res. 2008, 41: 629

<A NAME="RT13209SS-3A">3a</A> Roberts BA. Strauss CR. Acc. Chem. Res. 2005, 38: 653

<A NAME="RT13209SS-3B">3b</A> Kappe CO. Chem. Soc. Rev. 2008, 37: 1127

<A NAME="RT13209SS-3C">3c</A> Caddick S. Fitzmaurice R. Tetrahedron 2009, 65: 3325

<A NAME="RT13209SS-4">4</A> Cravotto G. Cintas P. Chem. Soc. Rev. 2006, 35: 180

<A NAME="RT13209SS-5">5</A> Ruecroft G. Hipkiss D. Ly T. Maxted N. Cains PW. Org. Process Res. Dev. 2005, 9: 923

<A NAME="RT13209SS-6">6</A> Cravotto G. Cintas P. Chem. Eur. J. 2007, 13: 1903

<A NAME="RT13209SS-7">7</A> Barge A. Tagliapietra S. Tei L. Cintas P. Cravotto G. Curr. Org. Chem. 2008, 12: 1588

<A NAME="RT13209SS-8">8</A> Van der Eycken E. Kappe CO. In Topics in Heterocyclic Chemistry Vol. 1: Springer; Berlin: 2006. p.267

<A NAME="RT13209SS-9">9</A> De Borggraeve WM. Rombouts FJR. Van der Eycken EV. Toppet SM. Hoornaert GJ. Tetrahedron Lett. 2001, 42: 5693

<A NAME="RT13209SS-10">10</A> 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

<A NAME="RT13209SS-11">11</A> 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

<A NAME="RT13209SS-12">12</A> Parlow JJ. Kurumbail RG. Stegeman RA. Stevens AM. Stallings WC. South MS. J. Med. Chem. 2003, 46: 4696

<A NAME="RT13209SS-13">13</A> Pawar VG. De Borggraeve WM. Synthesis 2006, 2799

<A NAME="RT13209SS-14">14</A> Kaval N. Bisztray K. Dehaen W. Kappe CO. Van der Eycken E. Mol. Diversity 2003, 7: 125

<A NAME="RT13209SS-15">15</A> Kaval N. Singh BK. Ermolat’ev DS. Claerhout S. Van der Eycken J. Van der Eycken E. J. Comb. Chem. 2007, 9: 446

<A NAME="RT13209SS-16">16</A> Kaval N. Van der Eycken J. Caroen J. Dehaen W. Strohmeier GA. Kappe CO. Van der Eycken E. J. Comb. Chem. 2003, 5: 560

<A NAME="RT13209SS-17">17</A> Azzam R. De Borggraeve WM. Compernolle F. Hoornaert GJ. Tetrahedron Lett. 2003, 61: 3953

<A NAME="RT13209SS-18">18</A> Appukkuttan P. Van der Eycken E. Eur. J. Org. Chem. 2008, 1133

<A NAME="RT13209SS-19">19</A> Mehta VP. Sharma A. Van der Eycken E. Org. Lett. 2008, 10: 1147

<A NAME="RT13209SS-20">20</A> Cravotto G. Palmisano G. Tollari S. Nano GM. Penoni A. Ultrason. Sonochem. 2005, 12: 91

<A NAME="RT13209SS-21">21</A> Cravotto G. Beggiato M. Palmisano G. Penoni A. Lévêque JM. Bonrath W. Tetrahedron Lett. 2005, 46: 2267

<A NAME="RT13209SS-22">22</A> Palmisano G. Bonrath W. Boffa L. Garella D. Barge A. Cravotto G. Adv. Synth. Catal. 2007, 349: 2338

<A NAME="RT13209SS-23">23</A> Palmisano G. Tagliapietra S. Barge A. Binello A. Cravotto G. Synlett 2007, 13: 2041

<A NAME="RT13209SS-24">24</A> Cravotto G. Garella D. Calcio Gaudino E. Lévêque J.-M. Chem. Today 2008, 26: 39

<A NAME="RT13209SS-25">25</A> Schröter S. Stock C. Bach T. Tetrahedron 2005, 61: 2245

<A NAME="RT13209SS-26">26</A> Singh BK. Mehta VP. Parmar VS. Van der Eycken E. Org. Biomol. Chem. 2007, 5: 2962