Photoinduced cyclization reactions in aqueous media

Current Organic Chemistry

Volumn 16, Issue 20, 2012, Pages 2379-2388

  Martín Flesia, Marina ^a   Postigo, Al ^a  

^a UNIVERSIDAD DE BUENOS AIRES   (Argentina)

Author keywords

Electrocyclic ring closure; Oxazolidinones; Photocyclization in aqueous media; Photocyclization of phthalimides

Indexed keywords

FREE RADICAL REACTIONS;

AQUEOUS MEDIA; ELECTROCYCLIC RING CLOSURE; ELECTROCYCLIC RINGS; OXAZOLIDINONES; PHOTOCYCLIZATION; PHOTOCYCLIZATION IN AQUEOUS MEDIUM; PHOTOCYCLIZATION OF PHTHALIMIDE; PHTHALIMIDE; RING CLOSURES;

CYCLIZATION;

EID: 84872502623     PISSN: 13852728     EISSN: None     Source Type: Journal    
DOI: 10.2174/138527212803520074     Document Type: Article

References (29)

1. Yorimitsu, T.; Nakamura, H.; Shinokubo, K.; Oshima, K.; Fujimoto, H. Powerful solvent effect of water in radical reaction: triethylborane-induced atom-transfer radical cyclization in water. J. Am. Chem. Soc., 2000, 122, 11041-11047.
2. 3SiH. Org. Lett., 2007, 9, 5159-5162.
3. Barata-Vallejo, S.; Postigo, A. Reactions of Fluorinated Organic Radicals in Aqueous Media, Eur.J. Org. Chem., 2012, 1889-1899.
4. Barata-Vallejo, S.; Nudelman, N.; Postigo, A. Organic Synthesis in Water Mediated by Silyl Radicals, Curr. Org. Chem., 2011, 15(11),1826-1842.
5. Postigo, A Nudelman, N. Synthetically-useful metal-mediated radical transformations in water and aqueous media. Coord. Chem. Rev., 2011, 255 (23-24), 2991-3030.
6. Kita, Y.; Nambu, H.; Ramesh, N.G.; Anikumar, G.; Matsugi, M. A novel and efficient methodology for the C-C bond forming radical cyclization of hydrophobic substrates in water. Org. Lett., 2001, 3, 1157-1160.
7. Nambu, H.; Anilkumar, G.; Matsugi, M.; Kita, Y. An efficient methodology for the C-C bond forming cyclization of hydrophobic substrates in water: effect of additive on radical reaction in water. Tetrahedron, 2003, 59, 77-85.
8. Breslow, R.; Rizzo, C.J. Chaotropic salt effects in a hydrophobically accelerated Diels-Alder reaction. J. Am. Chem. Soc., 1991, 113, 4340-4341.
9. Griesbeck, A.G.; Hoffmann, N.; Warcecha, K.D. Photoinduced-Electron-Transfer Chemistry: From Studies on PET Processes to Applications in Natural Product Synthesis. Acc. Chem. Res., 2007, 40, 128-140.
10. Griesbeck, A. G.; Hirt, J.; Kramer, W.; Dallakian, P. Photochemistry of Phthaloylcysteine, its Methyl Ester and C-Unprotected S-Alkyl Derivatives. Tetrahedron, 1998, 54, 3169-3180.
11. Griesbeck, A. G.; Hirt, J.; Peters, K.; Peters, E.-M.; von Schnering, H. G. Photochemistry of N-Phthaloylcysteine Derivatives: Multiplicity-Directed Regioselective CH Activation. Chem. Eur. J., 1996, 2, 1388-1394.
12. Griesbeck, A. G.; Kramer, W.; Oelgemöller, M. Synthetic Applications of Photoinduced Electron Transfer Decarboxylation Reactions. Synlett, 1999, 1169-1178.
13. Griesbeck, A.G.; Nerowski, F.; Lex, J. Decarboxylative Photocyclization: Synthesis of Benzopyrrolizidines and Macrocyclic Lactones. J. Org. Chem., 1999, 64, 5213-5217.
14. Griesbeck, A.G.; Guidapati, M.S.; Hirt, J.; Lex, J.; Oelgemoller, M.; Schmicklet, H.; Schoren, F. Photoinduced Electron-Transfer Reactions with Quinolinic and Trimellitic Acid Imides: Experiments and Spin Density Calculations. J. Org. Chem., 2000, 65, 7151-7157.
15. Griesbeck, A. G.; Henz, A.; Kramer, W.; Lex, J.; Nerowski, F.; Oelgemöller, M.; Peters, K.; Peters, E.-M. Synthesis of Medium-and Large-Ring Compounds Initiated by Photochemical Decarboxylation of ž-Phthalimidoalkanoates. Helv. Chim. Acta, 1997, 80, 912-933.
16. Yoon, U. C.; Oh, S. W.; Lee, S. M.; Cho, S. J.; Gamlin, J.; Mariano, P. S. A Solvent Effect That Influences the Preparative Utility of N-(Silylalkyl)phthalimide and N-(Silylalkyl)maleimide Photochemistry. J. Org. Chem., 1999, 64, 4411-4418.
17. Gö rner, H.; Oelgemö ller, M.; Griesbeck, A. G. Photodecarboxylation Study of Carboxy-Substituted N-Alkylphthalimides in Aqueous Solution. J. Phys. Chem. A, 2002, 106, 1458-1467.
18. Yoon, U.C.; Mariano, P.S. The Synthetic Potential of Phthalimide SET Photochemistry. Acc. Chem. Res., 2001, 34(7), 523-533.
19. Basarić, N. Horvat, M.; Mlinarić-Majerski, K.; Zimmermann, E.; Neudörfl, J.; Griesbeck, A.G. Novel 2,4-Methanoadamantane-Benzazepine by Domino Photochemistry of N-(1-adamantyl)phthalimide. Org. Lett., 2008, 10, 3965-3968.
20. Horvat, M.; Gorner, H.; Warzecha, K.-D.; Neudeorfl, J.; Griesbeck, A.G.; Mlinaric-Majerski, K; Basari, N. Photoinitiated Domino Reactions: N-(Adamantyl)phthalimides and N-(Adamantylalkyl)phthalimides. J. Org. Chem., 2009, 74, 8219-8231.
21. Görner, H.; Griesbeck, A. G.; Heinrich, T.; Kramer, W.; Oelgemöller, M. Time-Resolved Spectroscopy of Sulfur-and Carboxy-Substituted NAlkylphthalimides. Chem. Eur. J., 2001, 7, 1530-1538.
22. Basaric, N.; Horvat, M.; Frankovic, O.; Mlinarić-Majerski, K.; Neudörfl, J.; Griesbeck, A.G. Photoinduced hydrogen atom abstraction in N-(adamantyl)phthalimides: structure-reactivity study in the solid state. Tetrahedron, 2009, 65, 1438-1443.
23. Cindro, N.; Horvat, M.; Mlinaric-Majerski, K.; Griesbeck, A.G.; Basarić, N. Photoinduced homolytic C-H activation in N-(4-homoadamantyl) phthalimide. Beilstein J. Org. Chem., 2011, 7, 270-277.
24. Jia, J.; Sarker, M.; Steinmetz, M.G.; Shukla, R.; Rathore, R. Photochemical Elimination of Leaving Groups from Zwitterionic Intermediates Generated via Electrocyclic Ring Closure of α, β-Unsaturated Anilides. J. Org. Chem., 2008, 73, 8867-8879.
25. Kanaoka, Y.; Itoh, K.; Hatanaka, Y.; Flippen, J. L.; Karle, I. L.; Witkop, B. Photochemistry of the amide system. V. Synthetic photochemistry with heterocyclic anilides. Stereochemistry of the intramolecular 1,5-hydrogen shifts in nonoxidative photocyclization of benzo[b]thiophene-2-carboxanilides. J. Org. Chem., 1975, 40, 3001-3003.
26. Ma, C.; Chen, Y.; Steinmetz, M.G. Photochemical Cleavage and Release of Para-Substituted Phenols from α-Keto Amides. J. Org. Chem., 2006, 71, 4206-4215.
27. Ma, C.; Steinmetz, M. G.; Kopatz, E. J.; Rathore, R. Photochemical Cleavage and Release of Para-Substituted Phenols from α-Keto Amides. J. Org. Chem., 2005, 70, 4431-4442.
28. Ma, C.; Steinmetz, M. G.; Kopatz, E. J.; Rathore, R. Time-Resolved pH-Jump Study of Photochemical Cleavage and Release of Carboxylic Acids from a-Keto Amides. Tetrahedron Lett., 2005, 46, 1045-1048.
29. Ma, C.; Steinmetz, M. G.; Cheng, Q.; Jayaraman, V. Photochemical Cleavage and Release of Carboxylic Acids from α-Keto Amides. Org. Lett., 2003, 5, 71-74.