Phenylaza- and benzoazacrown compounds with a nitrogen atom conjugated with a benzene ring

Russian Chemical Reviews

Volumn 74, Issue 5, 2005, Pages 461-488

  Gromov, S P ^a   Dmitrieva, S N ^a   Churakova, M V ^a  

^a RUSSIAN ACADEMY OF SCIENCES   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 41949141302     PISSN: 0036021X     EISSN: 14684837     Source Type: Journal    
DOI: 10.1070/RC2005v074n05ABEH001163     Document Type: Review

References (225)

1. Y Inoue, G W Gokel (Eds) Cation Binding by Macrocycles (New York: Marcel Dekker, 1990)
2. R M Izatt, K Pawlak, J S Bradshaw, R L Bruening Chem. Rev. 91 1721 (1991)
3. A T Yordanov, D M Roundhill Coord. Chem. Rev. 170 93 (1998)
4. K Gloe, H Graubaum, M Wust, T Rambusch, W Seichter Coord. Chem. Rev. 222 103 (2001)
5. P Buhlmann, E Pretsch, E Bakker Chem. Rev. 98 1593 (1998)
6. M C Feiters, in Comprehensive Supramolecular Chemistry Vol. 10 (Ed. D N Reinhoudt) (Oxford: Pergamon Press, 1996) p. 267
7. A P de Silva, H Q N Gunaratne, T Gunnlaugsson, A J M Huxley, C P McCoy, J T Rademacher, T E Rice Chem. Rev. 97 1515 (1997)
8. M V Alfimov, S P Gromov, in Applied Fluorescence in Chemistry, Biology and Medicine (Eds W Rettig, B Strehmel, S Schrader, H Seifert) (Berlin: Springer, 1999) p. 161
9. B Valeur, I Leray Coord. Chem. Rev. 205 3 (2000)
10. S Shinkai, in Comprehensive Supramolecular Chemistry Vol. 1 (Ed. G W Gokel) (Oxford: Pergamon Press, 1996) p. 671
11. a
12. A Mishra, R K Behera, P K Behera, B K Mishra, G B Behera, Chem. Rev. 100 1973 (2000)
13. C J Pedersen J. Am. Chem. Soc. 89 7017 (1967)
14. J C Dabrowiak, P H Merrel, D H Busch Inorg. Chem. 11 1979 (1972)
15. G W Gokel, S H Korzeniowski, in Macrocyclic Polyether Synthesis (Berlin: Springer, 1982) p. 156
16. K E Krakowiak, J S Bradshaw, D J Zamecka-Krakowiak Chem. Rev. 89 929 (1989)
17. J S Bradshaw, K E Krakowiak, R M Izatt Aza-Crown Macrocycles (New York: Wiley, 1993)
18. A H M Elwahy J. Heterocycl. Chem. 40 1 (2003)
19. J P Dix, F Vögtle Angew. Chem. 90 893 (1978)
20. J P Dix, F Vögtle Chem. Ber. 113 457 (1980)
21. M P Vladimirova, S D Simova, E R Stanoeva, M I Mitewa Dyes Pigm. 50 157 (2001)
22. R A Schultz, B D White, D M Dishong, K A Arnold, G W Gokel J. Am. Chem. Soc. 107 6659 (1985)
23. Y Liu, Y Li, Y Chen, M Oichi, Y Inoue J. Chem. Res. (S) 216, (M) 1147 (1996)
24. W Zeng, Y Du, H Li, X Lu, S Qin Org. Prep. Proc. Int. 35 228 (2003)
25. T Gunnlaugsson, M Nieuwenhuyzen, L Richard, V Thoss Tetrahedron Lett. 42 4725 (2001)
26. T Gunnlaugsson, M Nieuwenhuyzen, L Richard, V Thoss J. Chem. Soc., Perkin Trans. 2 141 (2002)
27. Eur. Appl. 881 225; Chem. Abstr. 130 60 372 (1999)
28. Eur. Appl. 881 487; Chem. Abstr. 130 46 837 (1999)
29. H He, M A Mortellaro, M J P Leiner, S T Young, R J Fraatz, J K Tusa Anal. Chem. 75 549 (2003)
30. L Wu, X-P Qing, Z-H Tai, Q Bian, J-Q Zang, C-S Zhu Gaodeng Xuexiao Huaxue Xuebao 16 1550 (1995);
31. Chem. Abstr. 124 86 986 (1995)
32. J S Bradshaw, K E Krakowiak, G C Lindh, R M Izatt Tetrahedron 43 4271 (1987)
33. R C W Liu, P-S Fung, F Xue, T C W Mak, D K P Ng J. Chem. Res. (S) 414, (M) 1744 (1998)
34. T Hirano, K Kikuchi, Y Urano, T Higuchi, T Nagano Angew. Chem., Int. Ed. 39 1052 (2000)
35. C R Niu, H Jiang, C T Wu Chin. Chem. Lett. 9 17 (1998);
36. Chem. Abstr. 131 199 690 (1999)
37. C R Niu, H Jiang, C T Wu, B C Luo Chem. Res. Chin. Univ. 14 375 (1998);
38. Chem. Abstr. 130 296 673 (1999)
39. H Jiang, L R Chen. C R Niu Jiegou Huaxue 20 83 (2001);
40. Chem. Abstr. 135 19 611 (2001)
41. F Sancenon, R Martinez-Manez, J Soto Angew. Chem., Int. Ed. 41 1416 (2002)
42. H Sakamoto, J Ishikawa, M Otomo Bull. Chem. Soc. Jpn. 68 2831 (1995)
43. J Ishikawa, H Sakamoto, M Nakamura, K Doi, H Wada J. Chem. Soc., Dalton Trans. 191 (1999)
44. L R Hoover, T Pryor, J A Weitgenant, P E Willians, B N Storhoff, J C Huffman Phosphorus, Sulfur, Silicon Relat. Elem. 122 155 (1997)
45. J C Lockhart, A C Robson, M E Thompson, S D Furtado, C K Kaura, A R Allan J. Chem. Soc., Perkin Trans. 1 577 (1973)
46. WO PCT 82/04 253; Chem. Abstr. 98 179 431 (1983)
47. M J Calvertey, J Dale Acta Chem. Scand., Ser. B 36 241 (1982)
48. US P. 4 436 664; Chem. Abstr. 101 90 992 (1984)
49. US P. 4 597 903; Chem. Abstr. 105 153 087 (1986)
50. J-F Letard, S Delmond, R Lapouyade, D Braun, W Rettig, M Kreissler Recl. Trav. Chim. Pays.-Bas. 114 517 (1995)
51. B D White, D M Dishong, G Minganti, K A Arnold, D M Goli, G W Gokel Tetrahedron Lett. 26 151 (1985)
52. V J Gatto, G W Gokel J. Am. Chem. Soc. 106 8240 (1984)
53. C Blackburn, M Bai, K A Le Compte, M E Langmuir Tetrahedron Lett. 35 7915 (1994)
54. X-X Lu, S-Y Qin, Z-Y Zhou, V W-W Yam Inorg. Chem. Acta 346 49 (2003)
55. T Kikui, H Maeda, Y Nakatsuji, M Okahara Synthesis 74 (1984)
56. Jpn. P. 59 157 076; Chem. Abstr. 102 6566 (1985)
57. K Matsushima, Y Nakatsuji, N Kawamura, M Okahara J. Heterocycl. Chem. 23 255 (1986)
58. J P Dix, F Vögtle Chem. Ber. 114 638 (1981)
59. S A Jonker, F Ariese, J W Verhoeven Recl. Trav. Chim. Pays.-Bas. 108 109 (1989)
60. H Junek, M Klade, P Biza, M Geringer, H Sterk Liebigs Am. Chem. 741 (1990)
61. F Sancenon, R Martinez-Manez, M A Miranda, M-J Segui, J Soto Angew. Chem., Int. Ed. 42 647 (2003)
62. S Das, K G Thomas, K J Thomas, P V Kamat, M V George J. Phys. Chem. 98 9291 (1994)
63. D Ataman, E U Akkaya Tetrahedron Lett. 43 3981 (2002)
64. E I Ivanov, G V Fedorova Ukr. Khim. Zh., 52 1215 (1986)
65. Eur. P. 369 733; Chem. Abstr. 115 227 789 (1991)
66. B Leska, G Schröder, B Gierczyk Mod. Chem. 133 461 (1996)
67. B Gierczyk, B Leska, B Nowak-Wydra, G Schröder, G Wojciechowski, F Bartl, B Brzezinski J. Mol. Struct. 524 217 (2000)
68. G E Collins, L-S Choi, J H Callahan J. Am. Chem. Soc. 120 1474 (1998)
69. T Koike, T Gotoh, S Aoki, E Kimura, M Shiro Inorg. Chim. Acta 270 424 (1998)
70. M Subat, B Konig Synthesis 1818 (2001)
71. A J Pearson, W Xiao J. Org. Chem. 68 2161 (2003)
72. U Oguz, E U Akkaya J. Org. Chem. 63 6059 (1998)
73. D Citterio, S Sasaki, K Suzuki Chem. Lett. 552 (2001)
74. U Oguz, E U Akkaya Tetrahedron Lett. 39 5857 (1998)
75. B Witulski Synlett 1223 (1999)
76. X-X Zhang, S L Buchwald J. Org. Chem. 65 8027 (2000)
77. I P Beletskaya, A D Averin, A G Bessmertnykh, F Denat, R Guilard Tetrahedron Lett. 43 1193 (2002)
78. T Gunnlaugsson, H Q N Gunaratne, M Nieuwenhuyzen, J P Leonard J. Chem. Soc., Perkin Trans. 1 1954 (2002)
79. A Boila-Göckel, H Junek J. Prakt. Chem. 341 20 (1999)
80. S Fery-Forgues, J Bourson, L Dallery, B Valeur New J. Chem. 14 617 (1990)
81. A J Pearson, J-J Hwang Tetrahedron Lett. 42 3533 (2001)
82. Z Tai, X Qian, L Wu, C Zhu J. Chem. Soc., Chem. Commun. 1965 (1994)
83. A Boila-Göckel, W M F Fabian, H Junek Liebigs Am. Org. Bioorg. Chem. 397 (1996)
84. B S Muehl, B-J Sheu, S A Burns, J E Fritz, D A Tribbett, J A Weitgenant, B N Storhoff, J C Huffman J. Coord. Chem. 35 359 (1995)
85. K Kimura, R Mizutani, M Yokoyama, R Arakawa, Y Sakurai J. Am. Chem. Soc. 122 5448 (2000)
86. S Delmond, J-F Letard, R Lapouyade, R Mathevet, G Jonusauskas, C Rulliere New J. Chem. 20 861 (1996)
87. J Ishikawa, H Sakamoto, T Mizuno, M Otomo Bull. Chem. Soc. Jpn. 68 3071 (1995)
88. J Ishikawa, H Sakamoto, H Wada J. Chem. Soc., Perkin Trans. 2 1273 (1999)
89. H Sakamoto, J Ishikawa, T Mizuno, K Doi, M Otomo Chem. Lett. 609 (1993)
90. J Ishikawa, H Sakamoto, T Mizuno, K Doi, M Otomo Analyst 123 201 (1998)
91. J Ishikawa, H Sakamoto, M Otomo Analyst 122 1383 (1997)
92. N Marcotte, S Fery-Forgues, D Lavabre, S Marguet, V G Pivovarenko J. Phys. Chem. A 103 3163 (1999)
93. D B MacQueen, K S Schanze J. Am. Chem. Soc. 113 6108 (1991)
94. a
95. J-F Letard, R Lapouyade, W Rettig Pure Appl. Chem. 65 1705 (1993)
96. A Boila-Göckel, H Junek, P Czerney J. Prakt. Chem. 339 742 (1997)
97. J L Bricks, J L Slominskii, M A Kudinova, A I Tolmachev, K Rurack, U Resch-Genger, W Rettig J. Pholochem. Photobiol. A: Chem. 132 193 (2000)
98. a
99. a
100. a
101. S P Gromov, O A Fedorova, M V Alfimov Mol. Cryst. Liq. Cryst. 246 183 (1994)
102. a
103. b
104. a
105. M V Alfimov, A V Churakov, Y V Fedorov, O A Fedorova, S P Gromov, R E Hester, J A K Howard, L G Kuz'mina, I K Lednev, J N Moore J. Chem. Soc., Perkin Trans. 2 2249 (1997)
106. S Fery-Forgues, M-T Le Bris, J-P Guette, B Valeur J. Phys. Chem. 92 6233 (1988)
107. J Bourson, B Valeur J. Phys. Chem. 93 3871 (1989)
108. L Cazaux, M Faner, C Picard, P Tisnes Can. J. Chem. 71 1236 (1993)
109. P Dumon, G Jonusauskas, F Dupuy, Ph Pee, C Rulliere, J-F Letard, R Lapouyade J. Phys. Chem. 98 10391 (1994)
110. R Mathevet, G Jonusauskas, C Rulliere, J-F Letard, R Lapouyade J. Phys. Chem. 99 15709 (1995)
111. I K Lednev, O A Fyedorova, S P Gromov, M V Alfimov, J N Moore, R E Hester Spectrochim. Acta, Part A 49 1055 (1993)
112. S I Druzhinin, M V Rusalov, B M Uzhinov, M V Alfimov, S P Gromov, O A Fedorova Zh. Prikl. Spektrosk. 62 (3) 69 (1995)
113. S I Druzhinin, M V Rusalov, B M Uzhinov, M V Alfimov, S P Gromov, O A Fedorova Proc. Indian Acad. Sci. Chem. Sci. 107 721 (1995)
114. K Lednev, R E Hester, J N Moore J. Chem. Soc., Faraday Trans. 93 1551 (1997)
115. H-G Löhr, F Vögtle Acc. Chem. Res. 18 65 (1985)
116. S Fery-Forgues, M-T Le Bris, J-P Guette, B Valeur J. Chem. Soc., Chem. Commun. 384 (1988)
117. M M Martin, P Plaza, Y H Meyer, F Badaoui, J Bourson, J-P Lefevre, B Valeur J. Phys. Chem. 100 6879 (1996)
118. L Cazaux, M Faher, A Lopez, C Picard, P Tisnes J. Photochem. Photobiol. A: Chem. 77 217 (1994)
119. K J Thomas, K G Thomas, T K Manojkumar, S Das, M V George Proc. Indian Acad. Sci. Chem. Sci. 106 1375 (1994)
120. M M Martin, P Plaza, N Dai Hung, Y H Meyer, J Bourson, B Valeur Chem. Phys. Lett. 202 425 (1993)
121. S I Druzhinin, M V Rusalov, B M Uzhinov, S P Gromov, S A Sergeev, M V Alfimov J. Fluorescence 9 33 (1999)
122. L-J Zhang, H-K Lin, X-H Bu, Y-T Chen, X-L Liu, F-M Miao Inorg. Chim. Acta 240 257 (1995)
123. E Sonveaux Bull. Soc. Chim. Belg. 91 91 (1982)
124. E Sonveaux Tetrahedron 40 793 (1984)
125. A P de Silva, H Q Nimal Gunaratne, T Gunnlaugsson, M Nieuwenhuizen J. Chem. Soc., Chem. Commun. 1967 (1996)
126. K V Heyen, E Cielen, A Tahri, A Saleh, N Boens, G J Hoornaert Tetrahedron 55 5207 (1999)
127. J Petranek, O Ryba Collect. Czech. Chem. Commun. 45 1567 (1980)
128. S-H Chiu, K-S Liao, J-K Su Tetrahedron Lett. 45 213 (2004)
129. S Ghorbanian, L K Mehta, J Parrick, C H Robson Tetrahedron 55 14 467 (1999)
130. T Gunnlaugsson, J P Leonard J. Chem. Soc., Perkin Trans. 2 1980 (2002)
131. Z Hruska, J Petranek Polym. Bull. 103 (1987)
132. Z Hruska, J Petranek Collect. Czech. Chem. Commun. 53 68 (1988)
133. K Matsumoto, H Minatogawa, M Munakata, M Toda, H Tsukube Tetrahedron Lett. 31 3923 (1990)
134. H Tsukube, H Minatogawa, M Munakata, M Toda, K Matsumoto J. Org. Chem. 57 542 (1992)
135. Br. P. 2 277 096; Chem. Abstr. 122 50 761 (1995)
136. G A Artamkina, M V Ermolina, I P Beletskaya Mendeleev Commun. 158 (2003)
137. A Minta, R Y Tsien J. Biol. Chem. 264 19 449 (1989)
138. R Crossley, Z Goolamali, J J Gosper, P G Sammes J. Chem. Soc., Perkin Trans. 2 513 (1994)
139. T Gunnlaugsson, J P Leonard Chem. Commun. 2424 (2003)
140. J C Lockhart, M E Thompson J. Chem. Soc., Perkin Trans. 1 202 (1977)
141. J R Blackborow, J C Lockhart, D E Minnikin, A C Robson, M E Thompson J. Chromatogr. 107 380 (1975)
142. W Clegg, P J Cooper, J C Lockhart Acta Crystallogr., Sect. C 52 1795 (1996)
143. US P. 3 847 949; Chem. Abstr. 82 73 049 (1975)
144. C R Landis, R A Sawyer, E Somsook Organometallics 19 994 (2000)
145. R Glinka, E Mikiciuk-Olasik, B Kotelko Rocz. Chem. 51 351 (1977)
146. E Mikiciuk-Olasik, B Kotelko Pol. J. Chem. 58 1211 (1984)
147. S A G Hogberg, D J Cram J. Org. Chem. 40 151 (1975)
148. N Arnaud, C Picard, L Cazaux, P Tisnes Tetrahedron Lett. 36 5531 (1995)
149. B Cathala, C Picard, L Cazaux, P Tisnes, M Momtchev Tetrahedron 51 1245 (1995)
150. E Mikiciuk-Olasik Pharmazie 45 436 (1990)
151. R A Bartsch, E Chapoteau, B P Czech, J Krzykawski, A Kumar, T W Robison J. Org. Chem. 58 4681 (1993)
152. J P Hagemann, P T Kaye J. Chem. Soc., Perkin Trans. 1 341 (1999)
153. Eur. Appl. 881 488; Chem. Abstr. 130 60 373 (1999)
154. E Agar, S Sasmaz, N Akdemir, I Keskin J. Chem. Soc., Dalton Trans. 2087 (1997)
155. I P Beletskaya, A D Averin, A A Borisenko, F Denat, R Guilard Tetrahedron Lett. 44 1433 (2003)
156. A Masuyama, Y Nakamura, T Iwasaki, M Okahara Synth. Commun. 15 521 (1985)
157. T Ventrice, E M Campi, W R Jackson, A F Patti Tetrahedron 57 7557 (2001)
158. a
159. a
160. a
161. a
162. a
163. a
164. Russ. P. 2 161 153; Byull. Iizobr. (36) 320 (2000)
165. S P Gromov, S N Dmitrieva, A I Vedernikov, L G Kuz'mina, A V Churakov, Y A Strelenko, J A K Howard Eur. J. Org. Chem. 3189 (2003)
166. a
167. Russ. P. 2 215 738; Byull. Iizobr. (31) 484 (2003)
168. S P Gromov, S N Dmitrieva, M V Churakova Synthesis 593 (2003)
169. c
170. S N Dmitrieva, Candidate Thesis in Chemical Sciences, Photochemistry Centre of the Russian Academy of Sciences, Moscow, 2003
171. A I Vedernikov, Candidate Thesis in Chemical Sciences, Institute of Chemical Physics of the Russian Academy of Sciences, Moscow, 1997
172. a
173. d
174. L J Charbonniere, R F Ziessel Tetrahedron Lett. 41 2373 (2000)
175. B Agai, V Nemeth, Z Böcskei, K Simon, I Bitter, L Töke Tetrahedron 52 6713 (1996)
176. R Glinka Pol. J. Chem. 56 1139 (1982)
177. R Glinka, E Piatowska Pol. J. Chem. 58 259 (1984)
178. R Glinka, K Walczynski Acta Pol. Pharm. 43 32 (1986);
179. Chem. Abstr. 106 176 361 (1987)
180. R Glinka Pol. J. Chem. 54 1275 (1980)
181. J F Biernat, E Luboch Tetrahedron 40 1927 (1984)
182. R Glinka, E Piatowska, P Idowski Acta Pol. Pharm. 42 587 (1985);
183. Chem. Abstr. 106 156 445 (1987)
184. J F Biernat, E Jereczek, A Bujewski Pol. J. Chem. 53 2367 (1979)
185. T Tozawa, Y Misawa, S Tokita, Y Kubo Tetrahedron Lett. 41 5219 (2000)
186. A P de Silva, H Q Nimal Gunaratn, K R A Samankumara Sandanayake Tetrahedron Lett. 31 5193 (1990)
187. J C Aguilar, E R S Miguel, J Gyves, R A Bartsch, M Kim Talanta 54 1195 (2001)
188. R Crossley, Z Goolamali, P G Sammes J. Chem. Soc., Perkin Trans. 2 1615 (1994)
189. G A Smith, P G Morris, T R Hesketh, J C Metcalfe Biochim. Biophys. Acta 889 72 (1986)
190. S Qin Huaxue Xuebao 44 854 (1986);
191. Chem. Abstr. 107 59005 (1987)
192. d
193. d
194. d
195. USSR P. 1 356 410; Byull. Izobr. (12) 269 (1990)
196. USSR P. 1 405 274; Byull. Izobr. (21) 237 (1992)
197. USSR P. 1 392 869; Byull. Izobr. (21) 237 (1992)
198. USSR P. 1 415 708; Byull. Izobr. (21) 237 (1992)
199. e
200. f
201. S Kumar, V Bhalla, H Singh Tetrahedron 54 5575 (1998)
202. d
203. d
204. g
205. f
206. f
207. D Chen, J Huang, Q Huang, J Ji, X Huang, Y Yang, H Xu Huahue Xuebao 51 702 (1993);
208. Chem. Abstr. 119 249 935 (1993)
209. M Shamsipur, G Khayatian, S Y Kazemi, K Niknam, H Sharghi J. Inclusion Phenom. Macrocycl. Chem. 40 303 (2001)
210. B Gersch, J-M Lehn, E Grell Tetrahedron Lett. 37 2213 (1996)
211. Y Gök, A Demirbas Synth. React. Inorg. Met.-Org. Chem. 19 681 (1989)
212. H Kantekin, Ö Hasancebi, R Abbasoglu, Y Gök New J. Chem. 25 879 (2001)
213. Y Gök Polyhedron 15 1355 (1996)
214. P G Owston, R Peters, E Ramsammy, P A Tasker, J Trotter J. Chem. Soc., Chem. Commun. 1218 (1980)
215. P A Duckworth, L F Liudoy, M McPartlin, P A Tasker Aust. J. Chem. 46 1787 (1993)
216. K R Adam, B J McCool, A J Leong, L F Lindoy, C W G Ansell, P J Baillie, K P Dancey, L A Drummond, K Henrick, M McPartlin, D K Uppal, P A Tasker J. Chem. Soc., Dalton Trans. 3435 (1990)
217. K R Adam, D Baldwin, P A Duckworth, A J Leong, L F Lindoy, M McPartlin, P A Tasker J. Chem. Soc., Chem. Commun. 1124 (1987)
218. K Henrick, P M Judd, P G Owston, R Peters, P A Tasker, R W Turner J. Chem. Soc. Chem. Commun. 1253 (1983)
219. M Kawaguchi, J Ohashi Synthesis 701 (1985)
220. H Behr, E Breitmaier Chem. Ber. 111 913 (1978)
221. C W G Ansell, M F H Y J Chung, M McPartlin, P A Tasker J. Chem. Soc., Dalton Trans. 2113 (1982)
222. Y A Ibrahim, A H M Elwahy J. Chem. Res., (S) 252; (M) 1684 (1993)
223. H Hiller, P Dimroth, H Pfitzner Liebigs Ann. Chem. 717 137 (1968)
224. GDR P. 288 603; Chem. Abstr. 115 159 192 (1991)
225. J R Röper, H Elias Inorg. Chem. 31 1210 (1992)