Microwave-mediated synthesis and manipulation of a 2-substituted-5- aminooxazole-4-carbonitrile library

Tetrahedron Letters

Volumn 53, Issue 13, 2012, Pages 1656-1659

  Spencer, John ^a   Patel, Hiren ^a   Amin, Jahangir ^a   Callear, Samantha K ^b   Coles, Simon J ^b   Deadman, John J ^c   Furman, Christophe ^d   Mansouri, Roxane ^d   Chavatte, Philippe ^d   Millet, Régis ^d  

^a UNIVERSITY OF GREENWICH   (United Kingdom)

^b UNIVERSITY OF SOUTHAMPTON   (United Kingdom)

^c Avexa Ltd   (Australia)

^d Cité scientifique   (France)

Author keywords

Flow chemistry; Microwave assisted synthesis; Oxazoles; Parallel synthesis

Indexed keywords

5 (1H PYRROL 1 YL) 4 (1H TETRAZOL 5 YL) 2 (THIEN 2 YL)OXAZOLE; CANNABINOID 1 RECEPTOR; CANNABINOID 2 RECEPTOR; CCDC 850249; CCDC 850250; CCDC 850252; CCDC 850255; OXAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; BINDING AFFINITY; CRYSTAL STRUCTURE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; MICROWAVE IRRADIATION; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

EID: 84857373731     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.01.081     Document Type: Article

References (41)

1. See, for example: B. Wang, T.M. Hansen, L. Weyer, D. Wu, T. Wang, M. Christmann, Y. Lu, L. Ying, M.M. Engler, R.D. Cink, C.S. Lee, F. Ahmed, and C.J. Forsyth J. Am. Chem. Soc. 133 2011 1506 1516
2. M.C. Bagley, J.W. Dale, E.A. Meritt, and X. Xiong Chem. Rev. 105 2005 685 714
3. Z. Jin Nat. Prod. Rep. 28 2011 1143 1191
4. M.J. Thompson, H. Adams, and B. Chen J. Org. Chem. 74 2009 3856 3865
5. C. Verrier, T. Martin, C. Hoarau, and F. Marsais J. Org. Chem. 73 2008 7383 7386
6. S.A. Ohnmacht, P. Mamone, A.J. Culshaw, and M.F. Greaney Chem. Commun. 2008 1241 1243
7. J. Zhang, P.Y. Coqueron, J.P. Vors, and M.A. Ciufolini Org. Lett. 12 2010 3942 3945
8. N.A. Strotman, H.R. Chobanian, Y. Guo, J. He, and J.E. Wilson Org. Lett. 12 2010 3578 3581
9. B. Shi, A.J. Blake, W. Lewis, I.B. Campbell, B.D. Judkins, and C.J. Moody J. Org. Chem. 75 2010 152 161
10. F. Shibahara, E. Yamaguchi, and T. Murai J. Org. Chem. 76 2011 2680 2693
11. I.I.F. Boogaerts, and S.P. Nolan J. Am. Chem. Soc. 132 2010 8858 8859
12. B. Wu, J. Wen, J. Zhang, J. Li, Y.-Z. Xiang, and X.-Q. Yu Synlett 2009 500 504
13. C. Delvare, C.S. Harris, L. Hennequin, P. Koza, C. Lambert-van der Brempt, J. Pelleter, and O. Willerval ACS Comb. Sci. 13 2011 449 452
14. G.L. Thomas, E.E. Wyatt, and D.R. Spring Curr. Opin. Drug Discovery Dev. 9 2006 700 712
15. S. Dandapani, and L.A. Marcaurelle Curr. Opin. Chem. Biol. 14 2010 362 370
16. F. Freeman, and D. Kim Tetrahedron Lett. 30 1989 2631 2632
17. For related systems, see: M.B. Nolt, M.A. Smiley, S.L. Varga, R.T. McClain, S.E. Wolkenberg, and C.W. Lindsley Tetrahedron 62 2006 4698 4704
18. J. Spencer Fut. Med. Chem. 2 2010 161 168 and references therein
19. C.O. Kappe Angew. Chem., Int. Ed. 43 2004 6250 6284 and references therein
20. K.C. Miles, S.M. Mays, B.K. Southerland, T.J. Auvil, and D.M. Ketcha Arkivoc xiv 2009 181 190
21. P. Alexiou, and V.J. Demopoulos J. Med. Chem. 53 2010 7756 7766
22. M. Hadden, A. Goodman, C. Guo, P.R. Guzzo, A.J. Henderson, K. Pattamana, M. Ruenz, B.J. Sargent, B. Swenson, L. Yet, J. Liu, S. He, I.K. Sebhat, L.S. Lin, C. Tamvakopoulos, Q. Peng, Y. Kan, O. Palyha, T.M. Kelly, X.M. Guan, J.M. Metzger, M.L. Reitman, and R.P. Nargund Bioorg. Med. Chem. Lett. 20 2010 2912 2915
23. C. Biot, H. Bauer, R.H. Schirmer, and E. Davioud-Charvet J. Med. Chem. 47 2004 5972 5983
24. Z.P. Demko, and K.B. Sharpless Org. Lett. 3 2001 4091 4094
25. S.M. Lukyanov, I.V. Bliznets, S.V. Shorshnev, G.G. Aleksandrov, A.E. Stepanov, and A.A. Vasil'ev Tetrahedron 62 2006 1849 1863
26. M. Bauer, R.K. Harris, R.C. Rao, D.C. Apperley, and C.A. Rodger J. Chem. Soc., Perkin Trans. 2 1998 475 481
27. R.V. Jones, L. Godorhazy, N. Varga, D. Szalay, L. Urge, and F. Darvas J. Comb. Chem. 8 2006 110 116
28. K. Ito, T. Suzuki, Y. Sakamoto, D. Kubota, Y. Inoue, F. Sato, and S. Tokito Angew. Chem., Int. Ed. 42 2003 1159 1162
29. See for example: J.N. Heo, Y.S. Song, and B.T. Kim Tetrahedron Lett. 46 2005 4621 4625
30. J.P. Wolfe, and S.L. Buchwald J. Org. Chem. 65 2000 1144 1157
31. Q. Sheng, and J.F. Hartwig Org. Lett. 10 2008 4109 4112
32. For recent examples, see: A. Begouin, and M. Queiroz Eur. J. Org. Chem. 2009 2820 2827
33. F. Cardullo, D. Donati, G. Merlo, A. Paio, V. Petricci, and M. Taddei Synlett 2009 47 50
34. M.A. Letavic, and K.S. Ly Tetrahedron Lett. 48 2007 2339 2343
35. Recently reported aminocarbonylation processes are Pd-free, see for example: W. Ren, and M. Yamane J. Org. Chem. 75 2010 8410 8415
36. B. Roberts, D. Liptrot, L. Alcaraz, L.T. Luker, and M. Stocks J. Org. Lett. 12 2010 4280 4283
37. J. El Bakali, G.G. Muccioli, N. Renault, D. Pradal, M. Body-Malapel, M. Djouina, L. Hamtiaux, V. Andrzejak, P. Chavatte, P. Desreumeaux, D.M. Lambert, and R. Millet J. Med. Chem. 53 2010 7918 7931
38. For some of our earlier microwave chemistry, see: J. Spencer, H. Patel, R.P. Rathnam, and A. Nazira Tetrahedron 64 2008 10195 10200
39. J. Spencer, A. Nazira, H. Patel, R.P. Rathnam, and J. Verma Synlett 2007 2557 2558
40. For recent reviews, see: M. Congreve, G. Chessari, D. Tisi, and A.J. Woodhead J. Med. Chem. 51 2008 3661 3680
41. G.E. de Kloe, D. Bailey, R. Leurs, and I.J.P. de Esch Drug Discovery Today 14 2009 630 646