Photochemical rearrangement of N-mesyloxylactams: Stereospecific formation of N-heterocycles

Journal of Organic Chemistry

Volumn 76, Issue 1, 2011, Pages 164-169

  Drouin, Alexandre ^a   Winter, Dana K ^a   Pichette, Simon ^a   Aubert Nicol, Samuel ^a   Lessard, Jean ^a   Spino, Claude ^a  

^a UNIVERSITÉ DE SHERBROOKE   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

[CARBONYL; DEGREE OF SUBSTITUTION; N-HETEROCYCLES; PHOTOCHEMICAL REARRANGEMENT; RING CONTRACTION; RING SIZES; STEREOSPECIFIC;

CARBON; CARBONYL DERIVATIVE; HETEROCYCLIC COMPOUND; LACTAM DERIVATIVE; N MESYLOXYLACTAM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHIRALITY; CHLORINATION; CURTIUS REACTION; HOFMANN REACTION; LOSSEN REACTION; PHOTOCHEMISTRY; REACTION ANALYSIS; SCHMIDT REACTION; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

HETEROCYCLIC COMPOUNDS; LACTAMS; MESYLATES; MOLECULAR STRUCTURE; PHOTOCHEMICAL PROCESSES; STEREOISOMERISM;

EID: 78650876704     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101805q     Document Type: Article

References (43)

1. For selected books and reviews, see: Hesse, M. In The Alkaloids, Nature's Curse or Blessing?; Wiley VCH: Zürich, Switzerland, 2002; pp 1 - 413.
2. Michael, J. P. Nat. Prod. Rep. 2008, 25, 139 - 165.
3. Cordell, G. A. In The Alkaloids: Chemistry and Biology; Elsevier: San Diego, CA, 2003; Vol. 60, pp 1 - 282.
4. Kobayashi, J.; Morita, H. Alkaloids 2003, 60, 165-205
5. Yamamura, S. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1986; Vol. 29, 265 pp.
6. Moldvai, I.; Temesvari-Major, E.; Incze, M.; Doernyei, G.; Szentirmay, E.; Szantay, C. Helv. Chim. Acta 2005, 88, 1344-1356
7. Reynolds, T. Phytochemistry 2005, 66, 1399-1406
8. Lewis, J. R. Nat. Prod. Rep. 2001, 18, 95-128
9. Martin, S. F. Pure Appl. Chem. 1997, 69, 571-576
10. Kunz, H.; Pfrengle, W. Angew. Chem., Int. Ed. 1989, 28, 1067-1068
11. Pearson, W. H. Pure Appl. Chem. 2002, 74, 1339-1347
12. Fox, D. J.; House, D.; Warren, S. Angew. Chem., Int. Ed. 2002, 41, 2462-2482
13. Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 7324-7325
14. Shibata, I.; Kato, H.; Kanazawa, N.; Yasuda, M.; Baba, A. J. Am. Chem. Soc. 2004, 126, 466-467
15. Dieters, A.; Martin, S. F. Chem. Rev. 2004, 104, 2199-2238
16. Zeni, G.; Larock, R. C. Chem. Rev. 2006, 106, 4644-4680
17. Stanovnik, B.; Svete, J. Chem. Rev. 2004, 104, 2433-2480
18. Jagodzinski, T. S. Chem. Rev. 2003, 103, 197-228
19. Zeni, G.; Larock, R. C. Chem. Rev. 2004, 104, 2285-2310
20. Barluenga, J.; Santamaria, J.; Tomas, M. Chem. Rev. 2004, 104, 2259-2284
21. Fattorusso, E.; Taglialatela-Scafati, O. In Modern alkaloids; structure, isolation, synthesis and biology; WILEY-VCH, Weinheim, Germany, 2008; pp 1 - 665.
22. van der Eycken, E.; Kappe, C. O. In Microwave-Assisted Synthesis of Heterocycles, 1st ed.; Springer: Paris, France, 2006; pp 1 - 309.
23. Padwa, A.; Pearson, W. H. In Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products, 1st ed.; WILEY-Interscience: London, UK, 2002; pp 1 - 952.
24. El Ashry, E. S. H.; El Nemr, A. In Synthesis of Naturally Occurring Nitrogen Heterocycles from Carbohydrates, 1st ed.; WILEY-Blackwell: Oxford, UK, 2005; pp 1 - 464.
25. Eicher, T.; Hauptmann, S.; Suschitzky, H. In The Chemistry Of Heterocycles: Structure, Reactions, Syntheses and Applications, 2003 ed.; John WILEY & Sons: Etobicoke, Canada, 2002; pp 1 - 514.
26. Banthorpe, D. V. In The Chemistry of the Azido Group; Patai, S.; Wiley: New York, 1971; pp 1 - 626.
27. Walis, E. S.; Lane, J. F. Org. React. 1946, 3, 267-306
28. Wolff, H. Org. React. 1946, 3, 307-336
29. Smith, P. A. S. Org. React. 1946, 337-449
30. Senanayake, C. H.; Fredenburg, L. E.; Reamer, R. A.; Larsen, R. D.; Verhoeven, T. R.; Reider, P. J. J. Am. Chem. Soc. 1994, 116, 7947-7948
31. Gogoi, P.; Konwar, D. Tetrahedron Lett. 2007, 48, 531-533
32. Bauer, L.; Exner, O. Angew. Chem., Int. Ed. 1974, 13, 376
33. Lang, S.; Murphy, J. A. Chem. Soc. Rev. 2006, 35, 146-156
34. See, for example: Jianga, X.; Wanga, J.; Hua, J.; Gea, Z.; Hua, Y.; Hua, H.; Covey, D. F. Steroids 2001, 66, 655-662
35. Drouin, A.; Lessard, J. Tetrahedron Lett. 2006, 47, 4285-4288
36. Winter, D. K.; Drouin, A.; Lessard, J.; Spino, C. J. Org. Chem. 2010, 75, 2610-2618
37. Ogliaruso, M. A.; Wolfe, J. F. In Synthesis of Lactones and Lactams; John WILEY & Sons Inc.: Hoboken, NJ, 1993; pp 1 - 1100 and references cited therein.
38. For reviews, see: Arya, P.; Qin, H. Tetrahedron 2000, 56, 917-947 and references cited therein
39. Spino, C. Org. Prep. Proced. Int 2003, 35, 1-140
40. See the Supporting Information for the synthesis of the N -mesyloxy lactams.
41. Edwards et al. have reported that the photolysis of N -mesyloxy-4-aza-cholestane-3-one in methanol at room temperature gave the undesired ring contracted carbamate in 35% yield besides several other products. To the best of our knowledge, no further study of this reaction has been reported since. See: Edwards, O. E.; Grue-Sorensen, G.; Blackwell, B. A. Can. J. Chem. 1997, 75, 857-872
42. Di Maio and Tardella have reported two low-yielding examples of thermal ring-contraction of hydroxamic acid in phosphoric acid at 180 °C. See: DiMaio, G.; Tardella, P. A. Proc. Chem. Soc. 1963, 224
43. Błaszczyk, K.; Koenig, H.; Mel, K.; Paryzek, Z. Tetrahedron 2006, 62, 1069-1078 and references cited therein