Direct arylation of electron-poor indolizines

Tetrahedron

Volumn 70, Issue 2, 2014, Pages 225-231

  Koszarna, Beata ^a   Matczak, Rafał ^b   Krzeszewski, Maciej ^a   Vakuliuk, Olena ^b   Klajn, Jan ^a   Tasior, Mariusz ^a   Nowicki, Jan T ^b   Gryko, Daniel T ^a,b  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

^b WARSAW UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

Arylation; Dyes; Fluorescence; Heterocycles; Indolizines

Indexed keywords

INDOLIZINE DERIVATIVE;

ARTICLE; ARYLATION; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; FLUORESCENCE ANALYSIS; PRIORITY JOURNAL; QUANTUM YIELD;

EID: 84890788192     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2013.11.088     Document Type: Article

References (105)

1. V. Ntziachristos, J. Ripoll, L.V. Wang, and R. Weissleder Nat. Biotechnol. 23 2005 313 320
2. R. Weissleder Nat. Rev. 2 2002 11 18
3. B. Valeur Molecular Fluorescence Principles and Applications 2002 Wiley-VCH Weinheim
4. P. Mitchell Nat. Biotechnol. 19 2001 1013 1017
5. W.E. Moerner Acc. Chem. Res. 29 1996 563 571
6. Y. Xiao, F. Liu, X. Qian, and J. Cui Chem. Commun. 2005 239 241
7. M. Taki, T. Hohsaka, H. Murakami, K. Taira, and M. Sisido FEBS Lett. 507 2001 35 38
8. H.-C. Yeh, W.-C. Wu, and C.-T. Chen Chem. Commun. 2003 404 405
9. D. Kim, S. Singha, T. Wang, E. Seo, J.H. Lee, S.-J. Lee, K.H. Kim, and K.H. Ahn Chem. Commun. 2012 10243 10245
10. Y. Yamaguchi, T. Ochi, T. Wakamiya, Y. Matsubara, and Z. Yoshida Org. Lett. 8 2006 717 720
11. R. Mondal, B.K. Shah, and D.C. Neckers J. Org. Chem. 71 2006 4085 4091
12. T. Agou, J. Kobayashi, and T. Kawashima Org. Lett. 8 2006 2241 2244
13. S. Selvi, S.-C. Pu, Y.-M. Cheng, J.-M. Fang, and P.-T. Chou J. Org. Chem. 69 2004 6674 6678
14. K.S. Huang, M.J. Haddadin, M.M. Olmstead, and M.J. Kurth J. Org. Chem. 66 2001 1310 1315
15. M.J. Hall, L.T. Allen, and D.F. O'Shea Org. Biomol. Chem. 4 2006 776 780
16. M.D. Bowman, M.M. Jacobson, and H.E. Blackwell Org. Lett. 8 2006 1645 1648
17. R.Y. Chao, M.-F. Ding, J.-Y. Chen, C.-C. Lee, and S.-T. Lin J. Chin. Chem. Soc. 57 2010 213 221
18. X. Jin, C. Utamapiant, and A.Y. Ting ChemBioChem 12 2011 65 70
19. I. Kim, D. Kim, S. Sambasivan, and K.H. Ahn Asian J. Org. Chem. 1 2012 60 64
20. M. Tasior, R. Voloshchuk, Y.M. Poronik, T. Rowicki, and D.T. Gryko J. Porphyrins Phthalocyanines 15 2011 1011 1023
21. M.-S. Schiedel, C.A. Briehn, and P. Bäuerle Angew. Chem., Int. Ed. 40 2001 4677 4680
22. Angew. Chem. 113 2001 4813 4816
23. T. Mineno, T. Ueno, Y. Urano, H. Kojima, and T. Nagano Org. Lett. 8 2006 5963 5966
24. T. Hirano, K. Kikuchi, Y. Urano, T. Higuchi, and T. Nagano J. Am. Chem. Soc. 122 2000 12399 12400
25. P. Shieh, M.J. Hangauer, and C.R. Bertozzi J. Am. Chem. Soc. 134 2012 17428 17431
26. N. Boens, V. Leen, and W. Dehaen Chem. Soc. Rev. 41 2012 1130 1172
27. G. Ulrich, R. Ziessel, and A. Harriman Angew. Chem., Int. Ed. 47 2008 1184 1201
28. K.M. Kadish, K.M. Smith, and R. Guilard Handbook of Porphyrin Science Vol. 8 2010 World Scientific Singapore
29. T.A. Wood, and A. Thompson Chem. Rev. 107 2007 1831 1861
30. K. Kim, S.H. Choi, J. Jeon, H. Lee, J.O. Huh, J. Yoo, J.T. Kim, C.-H. Lee, Y.S. Lee, and D.G. Churchill Inorg. Chem. 50 2011 5351 5360
31. K. Kim, C. Jo, S. Easwaramoorthi, J. Sung, D.H. Kim, and D.G. Churchill Inorg. Chem. 49 2010 4881 4894
32. K. Kim, Y. Ha, L. Kaufman, and D.G. Churchill Inorg. Chem. 51 2012 928 938
33. K. Namba, A. Osawa, S. Ishizaka, N. Kitamura, and K. Tanino J. Am. Chem. Soc. 133 2011 11466 11469
34. D.T. Gryko, J. Piechowska, M. Tasior, J. Waluk, and G. Orzanowska Org. Lett. 8 2006 4747 4750
35. A. Janiga, E. Glodkowska-Mrowka, T. Stoklosa, and D.T. Gryko Asian J. Org. Chem. 2 2013 411 415
36. S. Matsumoto, E. Batmunkh, M. Akazome, Y. Takata, and M. Tamano Org. Biomol. Chem. 9 2011 5941 5944
37. M. Grzybowski, E. Glodkowska-Mrowka, T. Stoklosa, and D.T. Gryko Org. Lett. 14 2012 2670 2673
38. S. Matsumoto, H. Abe, and M. Akazome J. Org. Chem. 78 2013 2397 2404
39. K. Namba, A. Mera, A. Osawa, E. Sakuda, N. Kitamura, and K. Tanino Org. Lett. 14 2012 5554 5557
40. M. Tasior, V. Hugues, M. Blanchard-Desce, and D.T. Gryko Asian J. Org. Chem. 2 2013 669 673
41. D.A. Lerner, and E.M. Evleth Chem. Phys. Lett. 15 1972 260 262
42. D.A. Lerner, P.M. Horowitz, and E.M. Evleth J. Phys. Chem. 81 1977 12 16
43. T. Mitsumori, M. Bendikov, O. Dautel, F. Wudl, T. Shioya, H. Sato, and Y. Sato J. Am. Chem. Soc. 126 2004 16793 16803
44. Y.-M. Shen, G. Grampp, N. Leesakul, H.-W. Hu, and J.-H. Xu Eur. J. Org. Chem. 2007 3718 3726
45. J. Wan, C.-J. Zheng, M.-K. Fung, X.-K. Liu, C.-S. Lee, and X.-H. Zhang J. Mater. Chem. 22 2012 4502 4510
46. M.S. Jeong, E. Kim, H.J. Kang, E.J. Choi, A.R. Cho, S.J. Chung, and S.B. Park Chem. Commun. 2012 6553 6555
47. E. Kim, M. Koh, B.J. Lim, and S.B. Park J. Am. Chem. Soc. 133 2011 6642 6649
48. P.J. Aittala, O. Cramariuc, T.I. Hukka, M. Vasilescu, R. Bandula, and H. Lemmetyinen J. Phys. Chem. A 114 2010 7094 7101
49. M. Aginagalde, Y. Vara, A. Arrieta, R. Zangi, V.L. Cebolla, A. Delgado-Camon, and F.P. Cossio J. Org. Chem. 75 2010 2776 2784
50. F.D. Saeva, and H.R. Luss J. Org. Chem. 53 1988 1804 1806
51. H. Sonnenschein, G. Hennrich, U. Resch-Genger, and B. Schulz Dyes Pigments 46 2000 23 27
52. J.B. Henry, R.J. MacDonald, H.S. Gibbad, H. McNab, and A.R. Mount Phys. Chem. Chem. Phys. 13 2011 5235 5241
53. A. Vlahovici, I. Druta, M. Andrei, M. Cotlet, and R. Dinica J. Lumin. 82 1999 155 162
54. Y. Cheng, B. Ma, and F. Wudl J. Mater. Chem. 9 1999 2183 2188
55. A. Vlahovici, M. Andrei, and I. Druta J. Lumin. 96 2002 279 285
56. M. Vasilescu, R. Bandula, F. Dumitrascu, and H. Lemmetyinen J. Fluoresc. 16 2006 631 639
57. E. Kim, M. Koh, J. Ryu, and S.B. Park J. Am. Chem. Soc. 130 2008 12206 12207
58. Y. Lee, S. Na, S. Lee, N.L. Jeon, and S.B. Park Mol. BioSyst. 9 2013 952 956
59. A.V. Rotaru, I.D. Druta, T. Oeser, and T.J.J. Müller Helv. Chim. Acta 88 2006 1798 1812
60. F. Dumitrascu, M.T. Caproiu, F. Georgescu, B. Draghici, M.M. Popa, and E. Georgescu Synlett 2006 2407 2410
61. E. Georgescu, M.R. Caira, F. Georgescu, B. Draghici, M.M. Popa, and F. Dumitrascu Synlett 2009 1795 1799
62. M.R. Caira, E. Georgescu, F. Georgescu, F. Albota, and F. Dumitrascu Monatsh. Chem. 142 2011 743 748
63. Z. Chamas, E. Marchi, A. Modelli, Y. Fort, P. Ceroni, and V. Mamane Eur. J. Org. Chem. 2013 2316 2324
64. W. Flitsch Pyrroles with Fused Six-membered Heterocyclic Rings: (i) a-Fused A.R. Katritzky, C.W. Rees, Comprehensive Heterocyclic Chemistry Vol. 4 1984 Pergamon London, UK 443 495
65. E. Georgescu, F. Dumitrascu, F. Georgescu, C. Draghici, and L. Barbu J. Heterocycl. Chem. 50 2013 78 82
66. Y. Yang, C. Xie, Y. Xie, and Y. Zhang Org. Lett. 14 2012 957 959
67. Y. Liu, and J.-W. Sun J. Org. Chem. 77 2012 1191 1197
68. S. Chuprakov, and V. Gevorgyan Org. Lett. 9 2007 4463 4466
69. I.R. Lahoz, C. Sicre, A. Navarro-Vazquez, C. Silva Lopez, and M.-M. Cid Org. Lett. 11 2009 4802 4805
70. I. Kim, H. Kyoung Won, J. Choi, and G. Hyeoung Lee Tetrahedron 63 2007 12954 12960
71. Y. Jung, and I. Kim Tetrahedron 68 2012 8198 8206
72. D. Chernyak, C. Skontos, and V. Gevorgyan Org. Lett. 12 2010 3242 3245
73. Y. Liu, Z. Song, and B. Yan Org. Lett. 9 2007 409 412
74. O. Niyomura, Y. Yamaguchi, R. Sakao, M. Minoura, and Y. Okamoto Heterocycles 75 2008 297 304
75. H. Hu, K. Shi, R. Hou, Z. Zhang, Y. Zhu, and J. Zhou Synthesis 2010 4007 4014
76. H. Hu, J. Feng, Y. Zhu, N. Gu, and Y. Kan RSC Adv. 2 2012 8637 8644
77. I. Yavari, R. Hosseinpour, R. Pashazadeh, and S. Skoulika Synlett 2012 2103 2105
78. D. Basavaiah, B. Devendar, D.L. Lenin, and T. Satyanarayana Synlett 2009 411 416
79. F. Bellina, and R. Rossi Adv. Synth. Catal. 352 2010 1223 1276
80. J.M. Joo, B.B. Toure, and D. Sames J. Org. Chem. 75 2010 4911 4920
81. M. Poirier, S. Goudreau, J. Poulin, J. Savoie, and P.L. Beaulieu Org. Lett. 12 2010 2334 2337
82. O. Rene, and K. Fagnou Org. Lett. 12 2010 2116 2119
83. J. Pschierer, and H. Plenio Angew. Chem., Int. Ed. 49 2010 6224 6227
84. J.C. Lewis, A.M. Berman, R.G. Bergman, and J.A. Ellman J. Am. Chem. Soc. 130 2008 2493 2500
85. D. Alberico, M.E. Scott, and M. Lautens Chem. Rev. 107 2007 174 238
86. J. Roger, A.L. Gottumukkala, and H. Doucet ChemCatChem 2 2010 20 40
87. O. Vakuliuk, and D.T. Gryko Eur. J. Org. Chem. 2011 2854 2859
88. O. Vakuliuk, B. Koszarna, and D.T. Gryko Synthesis 2011 2833 2837
89. C.-H. Park, V. Ryabova, I.V. Seregin, A.W. Sromek, and V. Gevorgyan Org. Lett. 6 2004 1159 1162
90. D. Liegault, L. Lapointe, A. Caron, A. Vlassova, and K. Fagnou J. Org. Chem. 74 2009 1826 1834
91. O. Vakuliuk, B. Koszarna, and D.T. Gryko Adv. Synth. Catal. 353 2011 925 930
92. B. Zhao Org. Biomol. Chem. 10 2012 7108 7119
93. L. Moira, L. Bode, and T. Kaye J. Chem. Soc., Perkin Trans. 1 1993 1809 1813
94. D.R. Bragg, and D.G. Wibberley J. Chem. Soc. 1962 2627 2629
95. R.J. Hodgfiss, R.W. Middleton, J. Parrick, H.K. Rami, P. Wardman, and G.D. Wilson J. Med. Chem. 35 1992 1920 1926
96. R.M. Acheson, and J.McK. Woollard J. Chem. Soc. C 1971 3296 3305
97. A.H.M. de Vries, J.M.C.A. Mulders, J.H.M. Mommers, H.J.W. Henderickx, and J.G. de Vries Org. Lett. 5 2003 3285 3288
98. J. Roger, and H. Doucet Adv. Synth. Catal. 351 2009 1977 1990
99. J.J. Dong, D. Roy, R.J. Roy, M. Ionita, and H. Doucet Synthesis 2011 3530 3546
100. C. Fischmeister, and H. Doucet Green Chem. 13 2011 741 753
101. J. Roger, F. Požgan, and H. Doucet Adv. Synth. Catal. 352 2010 696 710
102. L. Chen, J. Roger, C. Bruneau, P.H. Dixneuf, and H. Doucet Chem. Commun. 2011 1872 1874
103. F. Požgan, J. Roger, and H. Doucet ChemSusChem 1 2008 404 407
104. M.O. Ogunrombi, S.F. Malan, G.T. Blanche, N. Castagnoli Jr., J.J. Bergh, and J.P. Petzer Bioorg. Med. Chem. 16 2008 2463 2472
105. N.V. Strashnikova, M.V. Sigalov, S.E. Korostova, A.E. Mikhaleva, and B.A. Trofimov Russian Chem. Bull. 42 1993 1013 1015