π-electron manipulation of the 5,6-dihydroxyindole/quinone system by 3-alkynylation: Mild acid-mediated entry to (Cross)-conjugated scaffolds and paradigms for medium-tunable chromophores

Journal of Organic Chemistry

Volumn 76, Issue 11, 2011, Pages 4457-4466

  Capelli, Luigia ^a   Crescenzi, Orlando ^a   Manini, Paola ^a   Pezzella, Alessandro ^a   Barone, Vincenzo ^b   Dischia, Marco ^a  

^a UNIVERSITY OF NAPLES FEDERICO II   (Italy)

^b SCUOLA NORMALE SUPERIORE   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION; ACETYLENE; CHARACTERIZATION; COMPLEXATION; ELECTRONIC PROPERTIES; PROTONATION; SCAFFOLDS;

ABSORPTION PROPERTY; ACETYL DERIVATIVES; CHEMICAL CHARACTERIZATION; DFT CALCULATION; ETHYNYL; INSOLUBLE MATERIALS; PHOSPHATE BUFFERS; PROTONATION EQUILIBRIA; RATIONAL DESIGN; REDOX BEHAVIOR; REDOX PROPERTY; STRUCTURAL MOTIFS;

CHROMOPHORES;

1 ACETYL 5,6 DIACETOXY 3 (TRIMETHYLSILYLETHYNYL)INDOLE; 1 ACETYL 5,6 DIACETOXY 3 ETHYNYLINDOLE; 3 ACETYL 5,6 DIACETOXYINDOLE; 3 ACETYL 5,6 DIHYDROXYINDOLE; 3 ETHYNYL 5,6 DIHYDROXYINDOLE; 3,3' (1,2 ETHYNEDIYL)BIS 5,6 DIHYDROXYINDOLE; 3,3' ETHENYLIDENEBIS 5,6 DIACETOXYINDOLE; 3,3' ETHENYLIDENEBIS 5,6 DIHYDROXYINDOLE; ACETIC ACID DERIVATIVE; EUMELANIN; INDOLE DERIVATIVE; PHOSPHATE BUFFERED SALINE; POLYMER; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ALKYNYLATION; ARTICLE; BIOTRANSFORMATION; CHEMICAL STRUCTURE; CHROMATOPHORE; CONJUGATION; CROSS COUPLING REACTION; DENSITY FUNCTIONAL THEORY; ELECTRON; ELECTRON TRANSPORT; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; OXIDATION; OXIDATION REDUCTION REACTION; PH; PROTON TRANSPORT; QUANTUM CHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 84961971266     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200232t     Document Type: Article

References (60)

1. Simon, J. D.; Peles, D. N. Acc. Chem. Res. 2010, 43, 1452-1460
2. dIschia, M.; Napolitano, A.; Pezzella, A.; Meredith, P.; Sarna, T. Angew. Chem., Int. Ed. 2009, 48, 3914-3921
3. Simon, J. D.; Peles, D.; Wakamatsu, K.; Ito, S. Pigment Cell Melanoma Res. 2009, 22, 563-579
4. dIschia, M.; Napolitano, A.; Pezzella, A.; Land, E. J.; Ramsden, C. A.; Riley, P. A. Adv. Heterocycl. Chem. 2005, 89, 1-63
5. Pezzella, A.; Crescenzi, O.; Natangelo, A.; Panzella, L.; Napolitano, A.; Navaratnam, S.; Edge, R.; Land, E. J.; Barone, V.; dIschia, M. J. Org. Chem. 2007, 72, 1595-1603
6. Napolitano, A.; Palumbo, A.; dIschia, M.; Prota, G. J. Med. Chem. 1996, 39, 5192-5201
7. Pezzella, A.; Panzella, L.; Natangelo, A.; Arzillo, M.; Napolitano, A.; dIschia, M. J. Org. Chem. 2007, 72, 9225-9230
8. Panzella, L.; Pezzella, A.; Napolitano, A.; dIschia, M. Org. Lett. 2007, 9, 1411-1414
9. Pezzella, A.; Panzella, L.; Crescenzi, O.; Napolitano, A.; Navaratnam, S.; Edge, R.; Land, E. J.; Barone, V.; dIschia, M. J. Am. Chem. Soc. 2006, 128, 15490-11221
10. dIschia, M.; Crescenzi, O.; Pezzella, A.; Arzillo, M.; Panzella, L.; Napolitano, A.; Barone, V. Photochem. Photobiol. 2008, 84, 600-607
11. Okuda, H.; Wakamatsu, K.; Ito, S.; Sota, T. J. Phys. Chem. A 2008, 112, 11213-11222
12. Okuda, H.; Wakamatsu, K.; Ito, S.; Sota, T. Chem. Phys. Lett. 2010, 490, 226-229
13. Pezzella, A.; dIschia, M.; Napolitano, A.; Palumbo, A.; Prota, G. Tetrahedron 1997, 53, 8281-8286
14. Watt, A. A. R.; Bothma, J. P.; Meredith, P. Soft Matter 2009, 5, 3754-3760
15. Meredith, P.; Sarna, T. Pigment Cell Res. 2006, 19, 572-594
16. Tran, M. L.; Powell, B. J.; Meredith, P. Biophys. J. 2006, 90, 743
17. Schweitzer, A. D.; Howell, R. C.; Jiang, Z.; Bryan, R. A.; Gerfen, G.; Chen, C.-C.; Mah, D.; Cahill, S.; Casadevall, A.; Dadachova, E. PLoS ONE 2009, 4, e7229
18. Ambrico, M.; Cardone, A.; Ligonzo, T.; Augelli, V.; Ambrico, P. F.; Cicco, S.; Farinola, G. M.; Filannino, M.; Perna, G.; Capozzi, V. Org. Electron. 2010, 11, 1809-1814
19. Bothma, J. P.; de Boor, J.; Divakar, U.; Schwenu, P. E.; Meredith, P. Adv. Mater. 2008, 20, 3539-3542
20. Panzella, L.; Pezzella, A.; Arzillo, M.; Manini, P.; Napolitano, A.; dIschia, M. Tetrahedron 2009, 65, 2032-2036
21. Arzillo, M.; Pezzella, A.; Crescenzi, O.; Napolitano, A.; Land, E. J.; Barone, V.; dIschia, M. Org. Lett. 2010, 12, 3250-3253
22. Pezzella, A.; Palma, A.; Iadonisi, A.; Napolitano, A.; dIschia, M. Tetrahedron Lett. 2007, 48, 3883-3886
23. Manini, P.; Pezzella, A.; Panzella, L.; Napolitano, A.; dIschia, M. Tetrahedron 2005, 61, 4075-4080
24. Manini, P.; dIschia, M.; Milosa, M.; Prota, G. J. Org. Chem. 1998, 63, 7002-7008
25. Pezzella, A.; Iadonisi, A.; Valerio, S.; Panzella, L.; Napolitano, A.; Adinolfi, M.; dIschia, M. J. Am. Chem. Soc. 2009, 131, 15270-15275
26. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467-4470
27. Chinchilla, R.; Najera, C. Chem. Rev. 2007, 107, 874-922
28. Wang, C.; Bryce, M. R.; Gigon, J.; Ashwell, G. J.; Grace, I.; Lambert, C. J. J. Org. Chem. 2008, 73, 4810-4818
29. Hauck, M.; Schönhaber, J.; Zucchero, A. J.; Hardcastle, K. I.; Müller, J. J.; Bunz, U. H. F. J. Org. Chem. 2007, 72, 6714-6725
30. Ma, C.; Lo, A.; Abdolmaleki, A.; MacLachlan, M. J. Org. Lett. 2004, 6, 3841-3844
31. Hsu, H.-F.; Lin, M.-C.; Lin, W.-C.; Lai, Y.-H.; Lin, S.-Y. Chem. Mater. 2003, 15, 2115-2118
32. Silvestri, F.; Marrocchi, A.; Seri, M.; Kim, C.; Marks, T. J.; Facchetti, A.; Taticchi, A. J. Am. Chem. Soc. 2010, 132, 6108-6123
33. Wang, C.; Palsson, L.-O.; Batsanov, A. S.; Bryce, M. R. J. Am. Chem. Soc. 2006, 128, 3789-3799
34. Capelli, L.; Manini, P.; Pezzella, A.; Napolitano, A.; dIschia, M. J. Org. Chem. 2009, 74, 7191-7194
35. Capelli, L.; Manini, P.; Pezzella, A.; dIschia, M. Org. Biomol. Chem. 2010, 8, 4243-4245
36. Failure to isolate intermediate oxidation products of 1 and 2 was attributed to the insolubility of the resulting oligomers, causing extraction only in trace amounts into organic solvents under the workup conditions preventing extraction into organic solvents under the usual workup conditions.
37. Panzella, L.; Manini, P.; Monfrecola, G.; dIschia, M.; Napolitano, A. Pigment Cell Res. 2006, 20, 128-133
38. Ito, S.; Wakamatsu, K. Pigment Cell Res. 2003, 16, 523-531
39. Miertus, S.; Scrocco, E.; Tomasi J. Chem. Phys. 1981, 55, 117-129
40. Cossi, M.; Scalmani, G.; Rega, N.; Barone, V. J. Chem. Phys. 2002, 117, 43-54
41. Scalmani, G.; Barone, V.; Kudin, K. N.; Pomelli, C. S.; Scuseria, G. E.; Frisch, M. J. Theor. Chem. Acc. 2004, 111, 90-100
42. Tomasi, J.; Mennucci, B.; Cammi, R. Chem. Rev. 2005, 105, 2999-3093
43. Ilichev, Y. V.; Simon, J. D. J. Phys. Chem. B 2003, 107, 7162-7171
44. Pezzella, A.; Panzella, L.; Crescenzi, O.; Napolitano, A.; Navaratnam, S.; Edge, R.; Land, E. J.; Barone, V.; dIschia, M. J. Org. Chem. 2009, 74, 3727-3734
45. Stark, K. B.; Gallas, J. M.; Zajac, G. W.; Eisner, M.; Golab, J. T. J. Phys. Chem. B 2003, 107, 3061-3067
46. Tarshits, D. L.; Przhiyalgovskaya, N. M.; Buyanov, V. N.; Tarasov, S. Y. Chem. Heterocycl. Compd. 2009, 45, 501-523
47. Edge, R.; dIschia, M.; Land, E. J.; Napolitano, A.; Navaratnam, S.; Panzella, L.; Pezzella, A.; Ramsden, C. A.; Riley, P. A. Pigment Cell Res. 2006, 19, 443-450
48. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, O.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision A.02; Gaussian, Inc.: Wallingford, CT, 2009.
49. Francl, M. M.; Petro, W. J.; Hehre, W. J. S.; Binkley, J.; Gordon, M. S.; DeFrees, D. J.; Pople, J. A. J. Chem. Phys. 1982, 77, 3654-3665
50. For a general introduction to basis sets, see: Foresman, J. B.; Frisch, A. Exploring Chemistry with Electronic Structure Methods, 2 nd ed.; Gaussian, Inc.: Pittsburgh, PA, 1996.
51. Adamo, C.; Barone, V. J. Chem. Phys. 1999, 110, 6158-6170
52. Rappé, A. K.; Casewit, C. J.; Colwell, K. S.; Goddard, W. A., III; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024-10035
53. York, D. A.; Karplus, M. J. Phys. Chem. A 1999, 103, 11060-11079
54. Scalmani, G.; Frisch, M. J. J. Chem. Phys. 2009, 132, 114110
55. Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. J. Phys. Chem. B 2009, 113, 6378-6396
56. Stratmann, R. E.; Scuseria, G. E.; Frisch, M. J. J. Chem. Phys. 1998, 109, 8218-8224
57. Bauernschmitt, R.; Ahlrichs, R. Chem. Phys. Lett. 1996, 256, 454-464
58. Casida, M. E.; Jamorski, C.; Casida, K. C.; Salahub, D. R. J. Chem. Phys. 1998, 108, 4439-4449
59. Adamo, C.; Scuseria, G. E.; Barone, V. J. Chem. Phys. 1999, 111, 2889-2899
60. Cossi, M.; Barone, V. J. Chem. Phys. 2001, 115, 4708-4717