Straightforward hetero Diels-Alder reactions of nitroso dienophiles by microreactor technology

Tetrahedron Letters

Volumn 51, Issue 44, 2010, Pages 5830-5833

  Monbaliu, Jean Christophe M R ^a   Cukalovic, Ana ^a   Marchand Brynaert, Jacqueline ^b   Stevens, Christian V ^a  

^a GHENT UNIVERSITY   (Belgium)

^b UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

Flow conditions; Hetero Diels Alder reaction; Microreactor; Nitroso dienophiles

Indexed keywords

ACYLNITROSODIENOPHILE; NITROSO DERIVATIVE; UNCLASSIFIED DRUG;

ACCURACY; ARTICLE; BIOREACTOR; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTINUOUS FLOW REACTOR; CYCLOADDITION; DIELS ALDER REACTION; FLOW RATE; MICROTECHNOLOGY; REACTION ANALYSIS;

ALNUS;

EID: 77957591552     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.08.117     Document Type: Article

References (43)

1. H. Yamamoto, and M. Kawasaki Bull. Chem. Soc. Jpn. 80 2007 595 607
2. S. Crotti, F. Bertolini, F. Macchia, and M. Pineschi Tetrahedron Lett. 51 2010 2284 2286
3. G. Calvet, S.C. Coote, N. Blanchard, and C. Kouklovsky Tetrahedron 66 2010 2969 2980
4. B.S. Bodnar, and M.J. Miller Tetrahedron Lett. 50 2009 796 798
5. B. Yang, and M.J. Miller J. Org. Chem. 74 2009 7990 7993
6. B.S. Bodnar, and M.J. Miller J. Org. Chem. 72 2007 3929 3938
7. C. Cesario, L.P. Tardibono Jr., and M.J. Miller Tetrahedron Lett. 51 2010 3053 3056
8. S. Yan, M.J. Miller, T.A. Wencewicz, and U. Möllmann Bioorg. Med. Chem. Lett. 20 2010 1302 1305
9. C. Cesario, and M.J. Miller J. Org. Chem. 74 2009 5730 5733
10. W. Lin, K.G. Virga, K.-H. Kim, J. Zajicek, D. Mendel, and M.J. Miller J. Org. Chem. 74 2009 5941 5946
11. D. Zhao, M. Johansson, and J.-E. Bäckvall Eur. J. Org. Chem. 2007 4431 4436
12. K. Kibayashi Chem. Pharm. Bull. 53 2005 1375 1386
13. S. Iwasa, K. Tajima, S. Tsushima, and H. Nishiyama Tetrahedron Lett. 42 2001 5897 5899
14. P. Quadrelli, M. Mella, A.G. Invernizzi, and P. Caramella Tetrahedron 55 1997 10497 10510
15. S.F. Martin, M. Hartman, and J.A. Josey Tetrahedron Lett. 33 1992 3583 3586
16. G.E. Keck Tetrahedron Lett. 48 1978 4767 4770
17. J.M. de los Santos, R. Ignacio, D. Aparicio, and F. Palacios J. Org. Chem. 72 2007 5202 5206
18. J. Streith, and A. Defoin Synthesis 1994 1107 1117
19. S. Iwasa, A. Fakhruddin, and H. Nishiyama Mini-Rev. Org. Chem. 2 2005 157 175
20. M.F.A. Adamo, and S. Bruschi J. Org. Chem. 72 2007 2666 2669
21. J. Corrie, G. Kirby, and J. Mackinnon J. Chem. Soc., Perkin Trans. 1 1985 883 886
22. G. Kirby, and J. Mackinnon J. Chem. Soc., Perkin Trans. 1 1985 887 892
23. G. Kirby, H. Mcguigan, and D. Mclean J. Chem. Soc., Perkin Trans. 1 1985 1961 1966
24. G. Kirby, H. Mcguigan, J. Mackinnon, D. Mclean, and R.P. Sharma J. Chem. Soc., Perkin Trans. 1 1985 1437 1442
25. C. Wiles, and P. Watts Eur. J. Org. Chem. 2008 1655 1671
26. C. Wiles, and P. Watts Expert Opin. Drug Disc. 2 2007 1487 1503
27. D.R.J. Acke, and C.V. Stevens Green Chem. 9 2007 386 390
28. D.R.J. Acke, C.V. Stevens, and B.I. Roman Org. Process Res. Dev. 12 2008 921 928
29. M. Damm, T.N. Glasnov, and C.O. Kappe Org. Process Res. Dev. 14 2010 215 224
30. W. Verboom Chem. Eng. Technol. 32 2009 1695 1701
31. G. Shore, and M.G. Organ Chem. Commun. 2008 838 840
32. Schwalbe, T.; Golbig, K.; Hohmann, M. et al. Miniaturized Reaction Apparatus. YMC Co Ltd, EP 1123734, 2001
33. www.thalesnano.com.
34. 1H NMR analysis of the crude reaction mixture and is relative to the diene. The yield is calculated after extraction. The regioisomer ratio is determined by analytical HPLC. The physical characterizations of all obtained products were in agreement with the reported data in the literature. See for example Ref. 7a and: J.-C. Monbaliu, and J. Marchand-Brynaert Tetrahedron Lett. 49 2008 1839 1842
35. Cyclopentadiene is freshly prepared before each run by thermal cracking of its dimer.
36. J.-C. Monbaliu, J. Marchand-Brynaert, and D. Peeters Tetrahedron Lett. 50 2009 2555 2558
37. 3) δ 148.27, 133.04, 131.01, 126.52, 125.37, 124.87, 123.21, 118.22, 72.30, 56.19, 18.50, 16.18, 13.81 ppm.
38. Monbaliu, J.-C.; Dive, G.; Marchand-Brynaert, J.; Peeters, D. J. Mol. Struct.: Theochem., submitted for publication.
39. See for example: L.R. Domingo, and J.A. Sez Org. Biomol. Chem. 7 2009 3576 3583
40. L.R. Domingo, J.A. Saéz, R.J. Zaragoz, and M. Arn J. Org. Chem. 73 2008 8791 8799 and references cited therein
41. 3) δ 169.54, 122.63, 122.13, 72.92, 44.93, 19.88, 15.43, 13.91 ppm.
42. 7a
43. Under similar conditions, no cycloadditions are observed in batch either.