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

Synlett

Volumn , Issue 10, 2006, Pages 1491-1496

  Appukkuttan, Prasad ^a   Husain, Mofazzal ^a,b,c   Gupta, Rajinder K ^c   Parmar, Virinder S ^b   Van Der Eycken, Erik ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

^b UNIVERSITY OF DELHI   (India)

^c GURU GOBIND SINGH INDRAPRASTHA UNIVERSITY   (India)

Author keywords

2(1H) pyrazinone; Cross coupling; Microwave; Simultaneous cooling; Stille

Indexed keywords

1,3 DIBENZYL 5 CHLORO 6 METHYLPYRAZIN 2(1H) ONE; 3 ALLYL 5 CHLORO 1 (3 PHENYLPROPYL) 2(1H) PYRAZINONE; 3 BENZYL 5 CHLORO 1 (4 METHOXYBENZYL) 2(1H) PYRAZINONE; 3 BENZYL 5 CHLORO 1 CYCLOHEXYL 2(1H) PYRAZINONE; 3 BENZYL 5 CHLORO 1 CYCLOHEXYLMETHYL 2(1H) PYRAZINONE; 3 BENZYL 5 CHLORO 1,6 DIPHENYL 2(1H) PYRAZINONE; 3 BENZYL 5 CHLORO(3 PHENYLPROPYL) 2(1H) PYRAZINONE; 3 BUTYL 5 CHLORO 1 (4 METHOXYBENZYL)PYRAZIN 2(1H) ONE; 3,5 DICHLORO 2(1H) PYRAZINONE DERIVATIVE; 5 CHLORO 1 (3 PHENYLPROPYL) 3 (3,4,5 TRIMETHOXYBENZYL) 2(1H) PYRAZINONE; 5 CHLORO 3 (2 FLUOROBENZYL) 1 (3 PHENYLPROPYL) 2(1H) PYRAZINONE; 5 CHLORO 3 (4 METHOXYBENZYL) 1 (3 PHENYLPROPYL) 2(1H) PYRAZINONE; 5 CHLORO 3 (4 METHOXYBENZYL) 1,6 DIPHENYL 2(1H) PYRAZINONE; BENZYL BROMIDE; HALIDE; N,N DIMETHYLFORMAMIDE; PYRAZINE DERIVATIVE; TOXIC SUBSTANCE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; COOLING; CROSS COUPLING REACTION; MICROWAVE IRRADIATION; PURIFICATION; STILLE REACTION; SYNTHESIS;

EID: 33745683813     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-941607     Document Type: Article

References (27)

1. (a) Hoornaert, G. Bull. Soc. Chim. Belg. 1994, 103, 583.
2. (b) Kaval, N.; Van der Eycken, J.; Caroen, J.; Dehaen, W.; Strohmeier, G. A.; Kappe, C. O.; Van der Eycken, E. J. Comb. Chem. 2003, 5, 560.
3. (c) Kaval, N.; Dehaen, W.; Van der Eycken, E. J. Comb. Chem. 2005, 7, 90; and references cited therein.
4. (d) Jiang, B.; Yang, C.-G.; Wang, J. J. Org. Chem. 2001, 66, 4865.
5. (e) Heeres, J.; de Jonge, M.R.; Koymans, L. M. H.; Daeyaert, F. F. D.; Vinkers, M.; Van Aken, K. J. A.; Arnold, E.; Das, K.; Kilonda, A.; Hoornaert, G. J.; Compernolle, F.; Cegla, M.; Azzam, R. A.; Andries, K.; de Bethune, M-P.; Azijn, H.; Pauwels, R.; Lewi, P. J.; Janssen, P. A. J. J. Med. Chem. 2005, 48, 1910.
6. (f) Parlow, J. J.; Case, B. L.; Dice, T. A.; Fenton, R. L.; Hayes, M. J.; Jones, D. E.; Neumann, W. L.; Wood, R. S.; Lachance, R. M.; Girard, T. J.; Nicholson, N. S.; Clare, M.; Stegeman, R. A.; Stevens, A. M.; Stallings, W. C.; Kurumbail, R. G.; South, M. S. J. Med. Chem. 2003, 46, 4050.
7. (a) Kaval, N.; Ermolat'ev, D.; Appukkuttan, P.; Dehaen, W.; Kappe, C. O.; Van der Eycken, E. J. Comb. Chem. 2005, 7, 490.
8. (b) Kaval, N.; Dehaen, W.; Kappe, C. O.; Van der Eycken, E. Org. Biomol. Chem. 2004, 2, 154.
9. (c) Van der Eycken, E.; Appukkuttan, P.; De Borggraeve, W.; Deahen, W.; Dallinger, D.; Kappe, C. O. J. Org. Chem. 2002, 67, 7904.
10. De Borggraeve, W. M.; Rombouts, F. J. R.; Van der Eycken, E. V.; Toppet, S. M.; Hoornaert, G. J. Tetrahedron Lett. 2001, 42, 5693.
11. Pawar, V. G.; De Borggraeve, W. M.; Macs, V.; Tourwe, D. A.; Compernolle, F.; Hoornaert, G. J. Tetrahedron Lett. 2005, 46, 1707.
12. De Borggraeve, W. M.; Verbist, B. M. P.; Rombouts, F. J. R.; Pawar, V. G.; Smets, W. J.; Kamoune, L.; Alen, J.; Van der Eycken, E. V.; Compernolle, F.; Hoornaert, G. J. Tetrahedron 2004, 60, 11597.
13. (a) Stille, J. K. Angew. Chem. 1986, 98, 504.
14. (b) Stille, J. K.; Simpson, J. H. J. Am. Chem. Soc. 1987, 109, 2138.
15. (c) Farina, V. Pure Appl. Chem. 1996, 68, 73.
16. (d) Bedford, R. B.; Hazelwood, S. L.; Limmert, M. E.; Albisson, D. A.; Draper, S. M.; Scully, P. N.; Coles, S. J.; Hursthouse, M. B. Chem. Eur. J. 2003, 9, 3216; and references cited therein.
17. Kaval, N.; Bisztray, K.; Dehaen, W.; Kappe, C. O.; Van der Eycken, E. Mol. Diversity 2003, 7, 125.
18. (a) Iyoda, M.; Miura, M.; Sasaki, S.; Kabir, S. M. H.; Kuwatani, Y.; Yoshida, M. Tetrahedron Lett. 1997, 38, 4581.
19. (b) Corsico, B. M.; Rossi, R. A. Synlett 2000, 230.
20. (c) Broutin, P.-E.; Čerňa, I.; Companiello, M.; Leroux, F.; Colbert, F. Org. Lett. 2004, 6, 4419.
21. (d) Cahiez, G.; Chaboche, C.; Mahuteau-Betzer, F.; Ahr, M. Org. Lett. 2005, 7, 1943.
22. (e) Micozzia, A.; Ottaviania, M.; Giardinaa, G.; Riccia, A.; Pizzoferratob, R.; Zillerb, T.; Compagnone, D.; Lo Sterzoc, C. Adv. Synth. Catal. 2005, 347, 143.
23. Arvela, R. K.; Leadbeater, N. E. Org. Lett. 2005, 7, 2101.
24. (a) Chen, J. J.; Deshpande, S. V. Tetrahedron Lett. 2003, 44, 8873.
25. (b) Humphrey, C. E.; Basson, M. A. M.; Tierney, J. P.; Turner, N. J. Org. Lett. 2003, 5, 849.
26. (c) Katritzky, A. R.; Zhang, Y.; Singh, S. K.; Steel, P. J. Arkivoc 2003, (xv), 47.
27. 2ClO: 324.1029; found: 324.1034.