Photoinduced decarboxylation of 3-(N-phthalimido)adamantane-1-carboxylic acid and radical addition to electron deficient alkenes

Photochemical and Photobiological Sciences

Volumn 10, Issue 4, 2011, Pages 610-617

  Horvat, Margareta ^a   Mlinarić Majerski, Kata ^a   Griesbeck, Axel G ^b   Basarić, Nikola ^a  

^a RUDER BO KOVI INSTITUTE   (Croatia)

^b UNIVERSITY OF COLOGNE   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 79953330376     PISSN: 1474905X     EISSN: 14749092     Source Type: Journal    
DOI: 10.1039/c0pp00357c     Document Type: Article

References (72)

1. Y. Kanaoka Photochemisry of cyclic imides. Examples of synthetic organic photochemistry Acc. Chem. Res. 1978 11 407 413
2. P. H. Mazzocchi, The photochemistry of imides, in Organic Photochemistry, ed., A. Padwa, A., Marcel Dekker, New York, 1981, vol 5; pp. 421-471
3. J. D. Coyle, in Synthetic Organic Photochemistry, ed., W. M. Horspool, Plenum Press, New York, 1984, pp. 259-284
4. H. Mauder and A. G. Griesbeck, Electron Transfer Processes in Phthalimide Systems, in CRC Handbook of Organic Photochemistry and Photobiology, ed., W. M. Horspool, P.-S. Song, CRC Press, Boca Raton, 1995, pp. 513-521
5. A. G. Griesbeck Photochemical activation of amino acids: from the synthesis of enantiomerically pure β,γ-unsaturated amino acids to macrocyclic ring systems Liebigs Ann. 1996 1951 1955
6. A. G. Griesbeck Photochemical transformations of proteinogenic and non-proteinogenic amino acids Chimia 1998 52 272 283
7. U. C. Yoon and P. S. Mariano, The Photochemistry of Silicon Substituted Phthalimides, in CRC Handbook of Organic Photochemistry and Photobiology, ed., W. M. Horspool, F. Lenci, CRC Press, Boca Raton, FL, 2004, 85, pp. 1-15
8. Y. Kanaoka K. Koyama Photochemistry of the phthalimide system: reduction, addition, and cyclization Tetrahedron Lett. 1972 13 4517 4520
9. N. Basarić M. Horvat K. Mlinarić-Majerski E. Zimmermann J. Neudörfl A. G. Griesbeck Novel 2,4-methanoadamantane-benzazepine by domino photochemistry of N-(1-adamantyl)phthalimide Org. Lett. 2008 10 3965 3968
10. M. Horvat H. Görner K.-D. Warzecha J. Neudörfl A. G. Griesbeck K. Mlinarić-Majerski N. Basarić Photoinitiated domino reactions: N-(adamantyl)phthalimides and N-(adamantylalkyl)phthalimides J. Org. Chem. 2009 74 8219 8231
11. G. McDermott D. J. Yoo M. Oelgemöller Photochemical addition reactions involving phthalimides Heterocycles 2005 65 2221 2257
12. P. H. Mazzocchi M. J. Bowen N. K. Narian Photochemical addition of dienes to N-alkylphthalimides J. Am. Chem. Soc. 1977 99 7063 7064
13. K. Maruyama Y. Kubo Addition of imides to olefins-remarkable difference between phthalimides and succinimides Chem. Lett. 1978 769 772
14. P. H. Mazzocchi S. Minamikawa M. J. Bowen Photochemical addition of alkenes to N-methylphthalimides. Formation of 3,4-benzo-6,7-dihydroazepine-2,5- diones J. Org. Chem. 1978 43 3079 3080
15. P. H. Mazzocchi S. Minamikawa P. Wilson Photochemical addition of alkenes to N-methylphthalimide. Stereochemistry of the addition J. Org. Chem. 1979 44 1186 1188
16. P. H. Mazzocchi F. Knackih P. Wilson Photochemical additions of alkenes to N-methylphthalimides. Effect of aryl substituents on the direction of addition J. Am. Chem. Soc. 1981 103 6498 6499
17. P. H. Mazzocchi P. Wilson F. Khachik L. Klinger S. Minamikawa Photochemical additions of alkenes to phthalimides. Mechanistic investigations on the stereochemistry of alkene additions and the effect of aryl substituents on the regiochemistry of alkene additions J. Org. Chem. 1983 48 2981 2989
18. U. C. Yoon P. S. Mariano The synthetic potential of phthalimide SET photochemistry Acc. Chem. Res. 2001 34 523 533 (Pubitemid 32816446)
19. M. Oelgemöller and A. G. Griesbeck, Single-Electron-Transfer Processes in Phthalimide Systems, in CRC Handbook of Organic Photochemistry and Photobiology, ed., W. M. Horspool, F. Lenci, CRC Press, Boca Raton, FL, 2004, pp. 1-19
20. U. C. Yoon and P. S. Mariano, Mechanistic and Synthetic Aspects of SET-Promoted Photocyclization Reactions of Silicon Substituted Phthalimides, in Organic Photochemistry and Photophysics; ed., V. Ramamurthy, K. Schanze, CRC Press, Taylor & Francis Group, Boca Raton, FL, 2006, pp. 179-206
21. A. G. Griesbeck N. Hoffmann K.-D. Warzecha Photoinduced-electron-transfer chemistry: from studies on PET processes to application in natural product synthesis Acc. Chem. Res. 2007 40 128 140
22. D. W. Leedy D. L. Muck Cathodic reduction of phthalimide systems in nonaqueous solutions J. Am. Chem. Soc. 1971 93 4264 4275
23. M. Oelgemöller A. G. Griesbeck Photoinduced electron transfer chemistry of phthalimdes: an efficient tool for C-C bond formation J. Photochem. Photobiol., C 2002 3 109 127 (Pubitemid 37379149)
24. 2 addition and electron transfer in the N-methylphthalimide-alkene system J. Org. Chem. 1985 50 2681 2684
25. P. H. Mazzocchi L. Klinger Photoreduction of N-methylphthalimide with 2,3-dimethyl-2-butene. Evidence for reaction through an electron transfer generated ion pair J. Am. Chem. Soc. 1984 106 7567 7572
26. Y. Kanaoka K. Sakai R. Murata Y. Hatanaka Photoaddition reactions of N-methylphthalimide with toluenes and amines Heterocycles 1975 3 719 722
27. Y. Sato H. Nakai T. Mizoguchi M. Kawanishi Y. Hatanaka Y. Kanaoka Photodecarboxylation of N-phthaloyl-a-amino acids Chem. Pharm. Bull. 1982 30 1263 1270
28. A. G. Griesbeck H. Mauder I. Müller E.-M. Peters K. Peters H. G. von Schnering Photochemistry of N-phthaloyl derivatives of methionine Tetrahedron Lett. 1993 34 453 456
29. A. G. Griesbeck J. Hirt E.-M. Peters H. G. von Schnering Photochemistry of N-phthaloyl derivatives: multiplicity-directed regioselective CH-activation Chem.-Eur. J. 1996 2 1388 1394 (Pubitemid 27027500)
30. A. G. Griesbeck W. Kramer M. Oelgemöller New tools in organic synthesis: PET-decarboxylation: scope and limitations Synlett 1999 1169 1178
31. K.-D. Warzecha H. Görner A. G. Griesbeck Photoinduced decarboxylative benzylation of phthalimide triplets with phenyl acetates: a mechanistic study J. Phys. Chem. A 2006 110 3356 3363
32. F. Hatoum S. Gallagher M. Oelgemöller Photodecarboxylative additions of phenoxyacetates to N-methylphthalimide Tetrahedron Lett. 2009 50 6593 6596
33. F. Hatoum S. Gallagher L. Baragwanath J. Lex M. Oelgemöller Photodecarboxylative benzylations of phthalimides Tetrahedron Lett. 2009 50 6335 6338
34. V. Belleau P. Noeureuil E. Ratzke A. Skvortsov S. Gallagher A. M. Cherri M. Oelgemöller Photodecarboxylative benzylations of phthalimide in pH 7 buffer: a simple access to 3-arylmethyleneisoindolin-1-ones Tetrahedron Lett. 2010 51 4738 4741
35. S. Gallagher F. Hatoum N. Zientek M. Oelgemöller Photodecarboxylative additions of N-protected a-amino acids to N-methylphthalimide Tetrahedron Lett. 2010 51 3639 6641
36. A. G. Griesbeck A. Henz K. Peters E.-M. Peters H. G. von Schnering Photoelectron transfer induced macrocyclization of N-phthaloyl-ω-amino- carboxylic acids Angew. Chem., Int. Ed. Engl. 1995 34 474 476
37. A. G. Griesbeck A. Henz W. Kramer J. Lex F. Nerowski M. Oelgemöller K. Peters J.-M. Peters Synthesis of medium- and large-ring compounds initiated by photochemical decarboxylation of ω-phthalimidoalkanoates Helv. Chim. Acta 1997 80 912 933 (Pubitemid 127494091)
38. A. G. Griesbeck F. Nerowski J. Lex Decarboxylative photocyclization: synthesis of benzopyrolizidines and macrocyclic lactones J. Org. Chem. 1999 64 5213 5216
39. U. C. Yoon S. W. Oh J. H. Lee J. H. Park K. T. Kang P. S. Mariano Applications of phthalimide photochemistry to macrocyclic polyether, polytioether and polyamide synthesis J. Org. Chem. 2001 66 939 943 (Pubitemid 32163092)
40. U. C. Yoon Y. X. Jin S. W. Oh C. H. Park J. H. Park C. F. Campana X. Cai E. N. Duesler P. S. Mariano A synthetic strategy for the preparation of cyclic peptide mimetics based on SET-promoted photocyclization processes J. Am. Chem. Soc. 2003 125 10664 10671 (Pubitemid 37055919)
41. U. C. Yoon H. C. Kwon T. G. Hyung K. H. Choi S. W. Oh S. Yang Z. Zhao P. S. Mariano The photochemistry of polydonor-substituted phthalimides: Curtin-Hammett type control of competing reactions of potentially interconverting zwitterionic-biradical intermediates J. Am. Chem. Soc. 2004 126 1110 1124 (Pubitemid 38140742)
42. D. W. Cho J. H. Choi S. W. Oh C. Quan U. C. Yoon R. Wang S. Yang P. S. Mariano Single electron transfer-promoted photocyclization reactons of linked acceptor-polydonor systems: effect of chain length and type on the efficiencies of macrocyclic ring-forming photoreactions of tethered α-silyl ether phthalimide substrates J. Am. Chem. Soc. 2008 130 2276 2284 (Pubitemid 351288005)
43. D. W. Cho C. Quan H. J. Park J. H. Choi S. R. Kim T. G. Hyung U. C. Yoon S. H. Kim Y. X. Jin P. S. Mariano Studies aimed at elucidating factors involved in the control of chemoselectivity in single electron transfer promoted photoreactions of branched-polydonor substituted phthalimides Tetrahedron 2010 66 3173 3186
44. A. G. Griesbeck T. Heinrich M. Oelgemöller J. Lex A. Molis A photochemical route for efficient cyclopeptide formation with minimum of protection and activation chemistry J. Am. Chem. Soc. 2002 124 10972 10973 (Pubitemid 35025644)
45. A. G. Griesbeck T. Heinrich M. Oelgemöller A. Molis A. Heidtmann Synthesys of cyclic peptides by photochemical decarboxylation of N-phthaloyl peptides in aqueous solution Helv. Chim. Acta 2002 85 4561 4578 (Pubitemid 36119163)
46. Y. Yoshimi M. Masuda T. Mizunashi K. Nishikawa K. Maeda N. Koshida T. Itou T. Morita M. Hatanaka Inter- and intramolecular addition reactions of electron-deficient alkenes with alkyl radicals, generated by SET-photochemical decarboxylation of carboxylic acids, serve as a mild and efficient method for the preparation of gama-amino acids and macrocyclic lactones Org. Lett. 2009 11 4652 4655
47. Y. Yoshimi K. Kobayashi H. Kamakura K. Nishikawa Y. Haga K. Maeda T. Morita T. Itou Y. Okada M. Hatanaka Addition of alkyl radicals, generated from carboxylic acids via photochemical decarboxylation, to glyoxylic oxime ether: a mild and efficient route to α-substituted α-aminoesters Tetrahedron Lett. 2010 51 2332 2334
48. . Horvat K. Mlinarić-Majerski Lj. Glava-Obrovac A. Jakas J. Veljković S. Marczi G. Kragol M. Roić M. Matković A. Milostić-Srb Tumor-cell-targeted methionine-enkephalin analogues containing unnatural amino acids: design, synthesis, and in vitro antitumor activity J. Med. Chem. 2006 49 3136 3142 (Pubitemid 43830512)
49. N. Basarić K. Molanov M. Matković B. Kojić- Prodić K. Mlinarić-Majerski Adamantane-retropeptides, new building blocks for molecular channels Tetrahedron 2007 63 7985 7996 (Pubitemid 47001965)
50. M. Matković J. Veljković K. Mlinarić-Majerski K. Molanov B. Kojić-Prodić Design of a depside with a lipophilic adamantane moiety: Synthesis, crystal structure and molecular conformation J. Mol. Struct. 2007 832 191 198 (Pubitemid 46367058)
51. Z. Dolić R. Margeta M. Vinković Z. tefanić B. Kojić- Prodić K. Mlinarić-Majerski M. inić N-Methylation of adamantane-substituted oxalamide unit affects its conformational rigidity: A skew conformation of the oxalamide bridge J. Mol. Struct. 2008 876 218 224
52. S. S. Novikov A. P. Hardin L. N. Butenko I. A. Kulev I. A. Novakov S. S. Radèenko S. S. Burdenko Synthesis and chemical transformation of acetylaminoadamantane derivatives Zh. Org. Khim. 1980 16 1433 1435
53. J. R. Geigy Neth. Appl. 6,600,715, July 21, 1966. Chem. Abstr. 1996 65 16975
54. H. Görner M. Oelgemöller A. G. Griesbeck Photodecarboxylation study of carboxy-substituted N-alkylphthalimides in aqueous solution: time resolved UV-Vis spectroscopy and conductometry J. Phys. Chem. A 2002 106 1458 1464 (Pubitemid 35264293)
55. M. Artico G. De Martino R. Giovanni Compounds with antiblastic activity. XXIX. 3-(p-Aminophenyl)coumarin derivatives Ann. Chim. 1966 56 1224 1236
56. A. H. Bedair R. Q. Lamphon S. S. Ghazal Synthesis and spectral studies on some 2-N-substituted phthalimides and phthaloyl p-aminophenyloxazolin-5-ones as possible antimicrobials J. Serb. Chem. Soc. 1987 52 477 486
57. A. H. Bedair F. M. Ali A. M. El-Agrody F. A. Eid M. A. A. El-Nassag G. El-Sherbeny Preparation of 4-aminophenylacetic acid derivatives with promising antimicrobial activity Acta Pharm. 2006 56 273 284 (Pubitemid 44422508)
58. H. Li J. Zhang Y. Zhou T. Li A rapid synthesys of N-aryl phthalimides under microwave irradiation in the absence of solvent Synth. Commun. 2002 32 927 930 (Pubitemid 34297157)
59. S. A. Worlikar R. C. Larock Palladium-Catalyzed One-Step Synthesis of Isoindole-1,3-diones by Carbonylative Cyclization of o-Halobenzoates and Primary Amines J. Org. Chem. 2008 73 7175 7180
60. J. D. Coyle A. Harriman G. L. Newport Reversible photorearrangement of N-substituted phthalimides a flash photolysis study J. Chem. Soc., Perkin Trans. 2 1979 799 802
61. V. Wingtens P. Valat J. Kossanyi L. Biczók A. Demeter T. Bérces Spectroscopic properties of aromatic dicarboximides J. Chem. Soc., Faraday Trans. 1994 90 411 421
62. A. G. Griesbeck H. Görner Laser flash photolysis of N-alkylated phthalimides J. Photochem. Photobiol., A 1999 129 111 119
63. H. Görner A. G. Griesbeck T. Heinrich W. Kramer M. Oelgemöller Time-resolved spectroscopy of sulfur- and carboxy-substituted N-alkylphthalimides Chem.-Eur. J. 2001 7 1530 1538 (Pubitemid 32288915)
64. R. E. Sioda W. S. Koski Electron spin resonance spectra of free radical anions of some cyclic anhydrides and imides in dimethylformamide solution J. Am. Chem. Soc. 1967 89 475 481
65. C. Amatore G. Capobianco G. Farnia G. Sandonà J. M. Savéant M. G. Severin E. Vianello Kinetics and mechanism of self-protonation reactions in organic electrochemical processes J. Am. Chem. Soc. 1985 107 1815 1824 (Pubitemid 15523310)
66. D. Mangion D. R. Arnold Photochemical nucleophile-olefin combination, aromatic substitution reaction. Its synthetic development and mechanistic exploration Acc. Chem. Res. 2002 35 297 304
67. M. Fagnoni M. Mella A. Albini Radical addition to alkenes via electron transfer photosensitization J. Am. Chem. Soc. 1995 117 7877 7881
68. M. Fiorentino L. Testaferri M. Tiecco L. Troisi Structural effects on the reactivity of carbon radicals in homolytic aromatic substitution. Part 4. The nucleophilicity of bridgehead radicals J. Chem. Soc., Perkin Trans. 2 1977 87 93
69. J. Fossey D. Lefort Etude du caractere nucleophile des radicaux lors de la reaction de transfert sur la liaison O-O des peracides Tetrahedron 1980 36 1023 1036
70. F. Recupero A. Bravo H.-R. Bjorsvik F. Fontana F. Minisci M. Piredda Enhanced nucleophilic character of the 1-adamantyl radical in chlorine atom abstraction and in addition to electron-poor alkenes and to protonated heteroaromatic bases. Absolute rate constants and relationship with the Gif reaction J. Chem. Soc., Perkin Trans. 2 1997 2399 2406
71. P. H. Mazzocchi L. Klinger Photoreduction of N-methylphthalimide with 2,3-dimethyl-2-butene. Evidence for reaction through an electron transfer generated ion pair J. Am. Chem. Soc. 1984 106 7567 7572
72. D. G. Herman S. J. Blanksby Investigation of the gas phase reactivity of the 1-adamantyl radical using a distonic radical anion approach Org. Biomol. Chem. 2007 5 3495 3503 (Pubitemid 47587702)