Microwave-assisted preparation of fused bicyclic heteroaryl boronates: Application in one-pot suzuki couplings

Journal of Organic Chemistry

Volumn 71, Issue 10, 2006, Pages 3959-3962

  DiMauro, Erin F ^a   Vitullo, Jason R ^a,b  

^a AMGEN INC   (United States)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BORON COMPOUNDS; MICROWAVES; MOLECULAR DYNAMICS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

BORONATES; BORONIC ESTER; ONE-POT SUZUKI COUPLINGS; REACTION CONDITIONS;

ESTERS;

BORON DERIVATIVE; BORONIC ESTER; ESTER; HETEROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHROMATOGRAPHY; CYCLIZATION; LITHIATION; MICROWAVE RADIATION; PURIFICATION; REACTION ANALYSIS; SUBSTITUTION REACTION; SUZUKI REACTION; SYNTHESIS;

EID: 33646497228     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060218p     Document Type: Article

References (34)

1. (a) For a review, see: Suzuki, A. J. Organomet. Chem. 1999, 576, 147-168.
2. (b) Bellina, F.; Carpita, A.; Rossi, R. Synthesis 2004, 15, 2419-2440.
3. (a) Zenk, R.; Partzsch, S.; Chimica Oggi 2003, 21, 70-73.
4. (b) Tyrrell, E.; Brookes, P. Synthesis 2003, 4, 469-483.
5. (a) Jones, G., Ed. Comprehensive Heterocyclic Chemistry. II. Volume 8: Fused Five-and Six-Membered Rings with Ring Junction Heteroatom; Pergamon: Oxford, 1996.
6. (b) Ramsden, C. A., Ed. Comprehensive Heterocyclic Chemistry. II. Volume 7: Fused Five-and Six-Membered Rings without Ring Junction Heteroatom; Pergamon: Oxford, 1996.
7. (a) Kappe, C. O.; Dallinger, D. Nat. Rev. Drug Discovery 2006, 5, 51-63.
8. (b) Besson, T.; Braun, C. T. In Microwave Assisted Organic Synthesis; Tierney, J. P., Lidström, P., Eds.; CRC Press: Boca Raton, FL, 2005; pp 44-74.
9. For a review on the synthesis of benzo[b]thiophenes, see: Rayner, C. M.; Graham, M. A. Sci. Synth. 2001, 10, 155-184.
10. For a review on the synthesis of benzo[b]furans, see: Dell, C. P. Sci. Synth. 2001, 10, 11-86.
11. For a review on the synthesis of azaindolizines (including imidazopyridines), see: Hajos, G.; Riedl, Z. Sci. Synth. 2002, 12, 613-678.
12. Gravel, M.; Thompson, M. Z.; Berube, C.; Hall, D. G. J. Org. Chem. 2002, 67, 3-15.
13. (a) Holland, R.; Spencer, J.; Deadman, J. J. Synthesis 2002, 2379-2382.
14. (b) Spencer, J.; Burd, A.; Goodwin, C. A.; Metrette, S. A. M.; Scully, M. F.; Adatia, T.; Deadman, J. J. Tetrahedron 2002, 58, 1551-1556.
15. (c) McKierman, G. J.; Hartley, R. C. Org. Lett. 2003, 5, 4389-4392.
16. (d) Bois-Choussy, M.; Cristau, P.; Zhu, J. Angew. Chem., Int. Ed. 2003, 42, 4238-4241.
17. (e) Kaiser, M.; Siciliano, C.; Assfalg-Machleidt, I.; Groll, M.; Milbradt, A. G.; Moroder, L. Org. Lett. 2003, 5, 3435-3437.
18. (f) Schulz, M. J.; Coats, S. J.; Hlasta, D. J. Org. Lett. 2004, 6, 3265-3268.
19. (g) Lautens, M.; Mancuso, J. J. Org. Chem. 2004, 69, 3478-3487.
20. (h) Moore, J. E.; York, M.; Harrity, J. P. A. Synlett 2005, 860-862.
21. (i) Moore, J. E.; Davies, M. W.; Goodenough, K. M.; Wybrow, R. A. J.; York, M.; Johnson, C. N.; Harrity, J. P. A. Tetrahedron 2005, 61, 6706-6714.
22. (j) Zhang, H.; Vogels, C. M.; Wheaton, S. L.; Baerlocher, F. J.; Decken, A.; Westcott, S. A. Synthesis 2005, 2739-2743.
23. Ishiyama, T.; Murata, M.; Miyaura, N. J. Org. Chem. 1995, 60, 7508-7510.
24. (a) Patel, M.; Rohde, J. J.; Kolasa, T. Tetrahedron Lett. 2003, 44, 6665-6667.
25. (b) Bridges, A. J.; Lee, A.; Schwartz, C. E.; Towle, M. J.; Littlefield, B. A. Bioorg. Med. Chem. 1993, 1, 403-410.
26. (c) Bridges, A. J.; Lee, A.; Maduakor, E. C.; Schwartz, C. E. Tetrahedron Lett. 1992, 33, 7499-7502.
27. (d) Osuga, H.; Suzuki, H.; Tanaka, K. Bull. Chem. Soc. Jpn. 1997, 70, 891-897.
28. To the best of our knowledge, there have been no prior reports of this cyclization in the presence of boronic ester or acid functionality.
29. Conditions examined: 4-chloro or 4-methoxybenzylmercaptan, various bases, μW, Δ.
30. 3, MS 4Å, 130 °C, 30 min, μW.; 50% conversion.
31. (a) Paizs, C.; Tosa, M.; Majdik, C.; Moldovan, P.; Novak, L.; Kolonits, P.; Marcovici, A.; Irimie, F.-D.; Poppe, L. Tetrahedron: Asymmetry 2003, 14, 1495-1501.
32. (b) D'Sa, B. A.; Kisanga, P.; Verkade, J. G. Synlett 2001, 670-672.
33. (c) Pestellini, V.; Giolitti, A.; Pasqui, F.; Abelli, L.; Cutrufo, C.; De Salvia, G.; Evangelista, S.; Meli, A. Eur. J. Med. Chem. 1988, 23, 203-206.
34. (d) Lamotte, G.; Demerseman, P.; Royer, R. Synthesis 1984, 1068-1070.