Photochemical and thermal ring-contraction of cyclic hydroxamic acid derivatives

Journal of Organic Chemistry

Volumn 77, Issue 24, 2012, Pages 11216-11226

  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

HIGH YIELD; HYDROXAMIC ACIDS; PHOTOCHEMICAL REARRANGEMENT; QUATERNARY CARBON; REGIOCHEMICAL; RING CONTRACTION; THERMAL REARRANGEMENT;

CHEMISTRY; ORGANIC COMPOUNDS;

ORGANIC ACIDS;

1 HYDROXY 3,3 DIPROPYLAZEPAN 2 ONE; 1 HYDROXY 6 METHYLPIPERIDIN 2 ONE; 1' HYDROXY 2,2 DIMETHYLTETRAHYDROSPIRO[CYCLOPENTA[D][1,3] DIOXOLE 5,3' PIPERIDIN] 2' ONE; 1' HYDROXY 6 OXASPIRO[BICYCLO[3.1.0]HEXANE 3,3' PIPERIDIN] 2' ONE; 3 (TERT BUTYLDIMETHYLSILYLOXY) 7 HYDROXY 6 OXO 7 AZASPIRO [4.5]DECAN 2 YL ACETATE; CARBON; HYDROXAMIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG STRUCTURE; PHOTOCHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SUBSTITUTION REACTION;

EID: 84871591863     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo3023507     Document Type: Article

References (21)

1. Lang, S.; Murphy, J. A. Chem. Soc. Rev. 2005, 35, 146-156
2. Kürti, L.; Czakó, B. In Strategic Applications of Named Reactions in Organic Synthesis; Elsevier Academic Press: Burlington, MA, 2005; pp 116-117, pp 210-211, pp 266-267, and pp 396-397.
3. Kyba, P. E. In Azides and Nitrenes: Reactivity and Utility; Scriven, E. F. V., Ed.; Academic Press: Orlando, FL, 1984; p 2.
4. Abramovich, R. A.; Kyba, E. P. In The Chemistry of the Azido Group; Patai, S. J., Ed.; Wiley & Sons: London, 1971; p 221.
5. Arya, P.; Qin, H. Tetrahedron 2000, 56, 917-947 and references cited therein
6. Davies, S. G.; Garner, A. C.; Roberts, P. M.; Smith, A. D.; Sweet, M. J.; Thomson, J. E. Org. Biomol. Chem. 2006, 4, 2753-2768
7. Palomo, C.; Oiarbide, M.; García, J. M. Chem. Soc. Rev. 2004, 33, 65-75
8. Dalko, P. I.; Moisan, L. Angew. Chem., Int. Ed. 2004, 43, 5128-5175
9. For a review on chiral enolate equivalents, see: Spino, C. Org. Prep. Proced. Int. 2003, 35, 1-140
10. The Hofmann rearrangement of cyclic imides is possible: Jiang, X.; Wang, J.; Hu, J.; Ge, Z.; Hu, Y.; Hu, H.; Covey, D. F. Steroids 2001, 66, 655-662
11. Drouin, A.; Lessard, J. Tetrahedron Lett. 2006, 47, 4285-4288
12. Winter, D. K.; Drouin, A.; Lessard, J.; Spino, C. J. Org. Chem. 2010, 75, 2610-2618
13. Drouin, A.; Winter, D. K.; Pichette, S.; Aubert-Nicol, S.; Lessard, J.; Spino, C. J. Org. Chem. 2011, 76, 164-169
14. Pichette, S.; Aubert-Nicol, S.; Lessard, J.; Spino, C. Eur. J. Org. Chem. 2012, 1328-1335
15. Edwards and co-workers have reported that the photolysis of N -mesyloxy-4-aza-cholestan-3-one in methanol at rt 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
16. Matlin, S. A.; Sammes, P. G. J. Chem. Soc., Chem. Commun. 1972, 1222-1223
17. Matlin, S. A.; Sammes, P. G.; Upton, R. M. J. Chem. Soc., Perkin Trans 1 1979, 2481-2487
18. Nesset, S. M.; Benneche, T.; Undheim, K. Acta Chem. Scand. 1993, 47, 1141-1143
19. Yamada, K.; Tanaka, S.; Naruchi, K.; Yamamoto, M. J. Org. Chem. 1982, 47, 5283-5289
20. Banerjee, R.; King, S. B. Org. Lett. 2009, 11, 4580-4583
21. For a leading reference and a more mechanistic discussion on the Schmidt rearrangement, see: Guttierez, O.; Aubé, J.; Tantillo, D. J. J. Org. Chem. 2012, 77, 640-647