Fused quinolines. recent synthetic approaches to azoloquinolines. A review

Heterocycles

Volumn 65, Issue 4, 2005, Pages 901-965

  Abass, Mohamed ^a  

^a Ain Shams University   (Egypt)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 30544453780     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/REV-04-592     Document Type: Review

References (172)

1. Milata V. In: Katritzky A.R. (Ed). Advances in Heterocyclic Chemistry: Tricyclic Azoloquinolines Vol. 78 (2001), Academic Press, Inc. 189-268
2. Majumdar K.C., and Das U. J. Indian Chem. Soc. 74 (1997) 884
3. Tsoi E., Charushin V.N., Nosova E.V., Lipunova G.N., and Tkachev A.V. Mendeleev Commun. (2001) 53
4. Tsoi E., Charushin V.N., Nosova E.V., Lipunova G.N., and Tkachev A.V. Chem. Abstr. 135 (2001) 210-924
5. Haldar P., Kar G.K., and Ray J.K. Tetrahedron Lett. 44 (2003) 7433
6. Glukhareva T.V., D'yachenko E.V., and Morzherin Yu.Yu. Khim. Geterotsikl. Soedin. 38 (2002) 1426
7. Glukhareva T.V., D'yachenko E.V., and Morzherin Yu.Yu. Chem. Abstr. 139 (2003) 133-516
8. Santos L.S., and Pilli R.A. Synthesis (2002) 87
9. 97 49709. Edwards J.P., Higuchi R., and Jones T. PCT Int. Appl. WO (1997)
10. Edwards J.P., Higuchi R., and Jones T. Chem. Abstr. 128 (1998) 114943
11. Zagoruiko M.A., Donchak L.N., and Kaminskii V.A. Zh. Org. Khim. 35 (1999) 141
12. Zagoruiko M.A., Donchak L.N., and Kaminskii V.A. Chem. Abstr. 131 (1999) 271799
13. Hamersak Z., Litvic M., Sepac D., Lesac A., Raza Z., and Sunjic V. Synthesis (2002) 2174
14. Gee M.B., Lee W.J., and Yum E.K. Bull. Korean Chem. Soc. 24 (2003) 1193
15. Fresneda P.M., Molina P., and Delagado S. Tetrahedron 57 (2001) 6197
16. Ono I., Ikegami T., and Inayoshi T. Bull. Chem. Soc. Jpn. 73 (2000) 575
17. Ono I., Ikegami T., and Inayoshi T. Chem. Abstr. 132 (2000) 341019
18. Anzini M., Cappelli A., Vomero S., Cagnotto A., and Skorupska M. J. Heterocycl. Chem. 29 (1992) 1111
19. Tominaga Y., Yoshioka N., Kataoka S., Shigemitsub Y., Hirota T., and Sasaki K. Heterocycles 50 (1999) 43
20. 064,897. Fourtillan J.-B., Fourtillan M., Jacquesy J.-C., Karam O., Zunino F., and Jouannetaud M.-P. PCT Int. Appl. WO (2000)
21. Fourtillan J.-B., Fourtillan M., Jacquesy J.-C., Karam O., Zunino F., and Jouannetaud M.-P. Chem. Abstr. 133 (2000) 321875
22. Anzini M., Cappelli A., and Vomero S. Heterocycles 38 (1994) 103
23. van Es T., Staskun B., and Fernandes M.A. S. Afr. J. Chem. 56 (2003) 30
24. van Es T., and Staskun B. S. Afr. J. Chem. 56 (2003) 40
25. Harayama T., Morikami Y., Shigeta Y., Abe H., and Takeuchi Y. Synlett (2003) 847
26. 73,305. Mekouar K., Genisson Y., Leue S., and Greene A.-E. PCT Int. Appl. WO (2000)
27. Mekouar K., Genisson Y., Leue S., and Greene A.-E. Chem. Abstr. 134 (2001) 5069
28. 022, 618. Leue S., Garcon S., Greene A.-E., Genisson Y., and Leon P. PCT Int. Appl. WO (2002)
29. Leue S., Garcon S., Greene A.-E., Genisson Y., and Leon P. Chem. Abstr. 136 (2002) 247732
30. Perzyna A., Houssin R., Barbry D., and Henichart J.-P. Synlett (2002) 2077
31. Miura Y., Fujimura Y., Takaku S., and Hamana M. Heterocycles 35 (1993) 693
32. Fan P., and Ablordeppy S.H. J. Heterocycl. Chem. 34 (1997) 1789
33. Molina P., Alajarrin M., and Sanchez-Andrada P. Synthesis (1993) 225
34. F. Makovec, A. Cappelli, M. Anzini, S. Vomero, and L. C. Rovati, U. S. Pat., 2002, 6,413,978.
35. Di Santo R., Costi R., Forte M., and Galeffi C. Arkivoc v (2004) 181. usa.org/ark/ARKIVOC/arkivoc_articles.asp
36. Viranyi A., Nyerges M., Blasko G., and Toke L. Synthesis (2003) 2655
37. Mekheimer R.A. Synthesis (2000) 2078
38. Bachy A., Fraisse L., Keane P., Mendes E., Vernieres J.C., and Simiand J. Eur. Pat. Appl. EP 587 (1994) 473
39. Bachy A., Fraisse L., Keane P., Mendes E., Vernieres J.C., and Simiand J. Chem. Abstr. 121 (1994) 108763
40. Chen Y.-L., Chung C.-H., Chen I.-L., Chen P.H., and Jeng H.Y. Bioorg. Med. Chem. 10 (2002) 2705
41. 1,696. Choi J.-K., Yum E.K., Kim S.S., Kang S.K., Cheon H.G., and Kim H.J. PCT Int. Appl. WO (2000)
42. Choi J.-K., Yum E.K., Kim S.S., Kang S.K., Cheon H.G., and Kim H.J. Chem. Abstr. 132 (2000) 93305
43. Nyerges M., Fejes I., and Toke L. Synthesis (1992) 1823
44. Malassene R., Sanchez-Bajo L., Toupet L., Hurvois J.-P., and Moinet C. Synlett 1500 (2002)
45. Hara 'O., Sugimoto K., Makino K., and Hamada Y. Synlett (2004) 1625
46. 44,342. Choi J.-K., Kim S.S., Yum E.K., Cho S.Y., and Kang S.K. PCT Int. Appl. WO (1997)
47. Choi J.-K., Kim S.S., Yum E.K., Cho S.Y., and Kang S.K. Chem. Abstr. 128 (1998) 34754
48. Stadlbauer W., Laschober R., and Kappe T. Monatsh. Chem. 122 (1991) 853
49. Jonckers T.H.M., Maes B.U.W., Lemiere G.L.F., Rombouts G., Pieters L., Haemers A., and Dommisse R.A. Synlett (2003) 615
50. Abass M. Synth. Commun. 30 (2000) 2735
51. Mouaddib A., Joseph B., Hasnaoui A., and Merour J.Y. Synthesis (2000) 549
52. Vlachou M., Tsotinis A., Kelland L.R., and Thurston D.E. Heterocycles 57 (2001) 129
53. Majumdar K.C., Biswas P., and Jana G.H. J. Chem. Research, Synop. (1997) 310
54. Majumdar K.C., Biswas P., and Jana G.H. J. Chem. Research, Synop. (M) (1997) 2067
55. 066,475. Zhi L., Van Oeveren C.A., Chen J.-H., and Higuchi R.I. PCT Int. Appl. WO (2002)
56. Zhi L., Van Oeveren C.A., Chen J.-H., and Higuchi R.I. Chem. Abstr. 137 (2002) 201294
57. Zhang Z., Tillekeratne L.M.V., and Hudson R.A. Synthesis (1996) 377
58. Aragon P.-J., Yapi A.-D., Pinguet F., Chezal J.-M., Teulade J.-C., Chapat J.-P., and Blache Y. Chem. Pharm. Bull. 52 (2004) 659
59. Trecourt F., Mongin F., Mallet M., and Queguiner G. J. Heterocycl. Chem. 32 (1995) 1261
60. Suh M.-E., Park S.-Y., and Lee C.-C. Bioorg. Med. Chem. 9 (2001) 2979
61. Suh M.-E., and Shin S.-H. Yakhak Hoechi 41 (1997) 575
62. Suh M.-E., and Shin S.-H. Chem. Abstr. 128 (1997) 88804
63. Barret R., Roue N., and Fillion H. Chem. Pharm. Bull. 46 (1998) 548
64. Delest B., Tisserand J.-Y., Robert J.-M., Nourrisson M.-R., Pinson P., Duflos M., Le Baut G., Renard P., and Pfeiffer B. Tetrahedron 60 (2004) 6079
65. Mukhanova T.I., Alekseeva L.M., Shashkov A.S., and Granik V.G. Khim. Geterotsikl. Soedin. 40 (2004) 20
66. Translate:. Mukhanova T.I., Alekseeva L.M., Shashkov A.S., and Granik V.G. Chem. Heterocycl. Comp. 40 (2004) 16
67. Barraja P., Diana P., Lauria A., Montalbano A., Almerico A.M., Dattolo G., Cirrincione G., Viola G., and Dall'Acqua F. Bioorg. Med. Chem. Lett. 13 (2003) 2809
68. El Ouar M., Knouzi N., and Hamelin J. J. Chem. Research, Synop. (1998) 92
69. Majumdar K.C., Chattopadhyay S.K., and Khan A.T. J. Chem. Soc., Perkin Trans. 1 (1989) 1285
70. Kappe T., Roschger P., Schuiki B., and Stadlbauer W. J. Heterocycl. Chem. 40 (2003) 297
71. Kutyrev A., and Kappe T. J. Heterocycl. Chem. 34 (1997) 969
72. Tolkunov S.V., Khyzhan A.I., Shishkina S.V., Shishkin O.V., and Dulenko V.I. Khim. Geterotsikl. Soedin. 40 (2004) 64
73. Translate. Tolkunov S.V., Khyzhan A.I., Shishkina S.V., Shishkin O.V., and Dulenko V.I. Chem. Heterocycl. Comp. 40 (2004) 58
74. Rajmanickam P., and Shanmugam P. Z. Naturforsch. B: Chem. Sci. 48 (1993) 517
75. Traven V.F., Podkhalyuzina N.Ya., and Kanevskii D.S. Khim. Geterotsikl. Soedin. 38 (2002) 359
76. Traven V.F., Podkhalyuzina N.Ya., and Kanevskii D.S. Chem. Abstr. 138 (2003) 122-569
77. Subramaniam M., Prasad K.J.R., and Shanmugam P. Synthesis (1989) 777
78. Gunasekaran C., and Prasad K.J.R. Indian J. Heterocycl. Chem. 5 (1996) 169
79. Gunasekaran C., and Prasad K.J.R. Chem. Abstr. 125 (1996) 86529
80. Sekar M., and Prasad K.J.R. J. Nat. Prod. 61 (1998) 294
81. Butenschon I., Moller K., and Hansel W. J. Med. Chem. 44 (2001) 1249
82. Reisch J., and Nordhaus P. Monatsh. Chem. 125 (1994) 225
83. Bar G., Parsons A.F., and Thomas C.B. Tetrahedron 57 (2001) 4719
84. Jnaneshwara G.K., Shaikh N.S., Bapat N.Y., and Deshpande V.H. J. Chem. Research, Synop. (2000) 34
85. Del Bosque J.R., Martin N., Mora A., Morales A., Quinteiro M., Seoane C., Soto J.L., and Suarez M. An. Quim. 90 (1994) 511
86. Del Bosque J.R., Martin N., Mora A., Morales A., Quinteiro M., Seoane C., Soto J.L., and Suarez M. Chem. Abstr. 123 (1995) 339806
87. Radl S., Urbankova J., Vachal P., and Taimr J. Electronic Conference on Heterocyclic Chemistry (ECHET98) (1998). http://www.ch.ic.ac.uk/ectoc/echet98/ectocma.html
88. Majdumar K.C., Kundu A.K., and Chatterjee P. J. Chem. Research, Synop. (1995) 386
89. Majdumar K.C., and Kundu A.K. Heterocycles 45 (1997) 1467
90. Majdumar K.C., Kundu A.K., and Biswas P. Heterocycles 51 (1999) 471
91. Majdumar K.C., Kundu A.K., and Biswas P. Heterocycles 51 (1999) 2399
92. Klasek A., and Kafka S. J. Heterocycl. Chem. 35 (1998) 307
93. Majumdar K.C., and Kundu A.K. Synth. Commun. 26 (1996) 4023
94. Meth-Cohn O., and Taylor D.L. Tetrahedron Lett. 34 (1993) 3629
95. Majumdar K.C., and Bhattacharyya T. J. Chem. Research, Synop. (1997) 244
96. Nair V., Menon R.S., Vinod A.U., and Viji S. Tetrahedron Lett. 43 (2002) 2293
97. Lee Y.R., Byun M.W., and Kim B.S. Bull. Korean Chem. Soc. 19 (1998) 1080
98. Reisch J., and Iding M. Pharmazie 49 (1994) 62
99. Klasek A., Koristek K., Sedmera P., and Halada P. Heterocycles 60 (2003) 799
100. Chen L., Li Z., and Li C.-J. Synlett (2003) 732
101. Yadav J.S., Reddy B.V.S., Uma Gayathri K., and Prasad A.R. Synthesis (2002) 2537
102. Wang Y.-G., Lin X.-F., and Cui S.-L. Synlett (2004) 1175
103. Srinivas K.V.N.S., and Das B. Synlett (2004) 1715
104. Yadav J.S., Reddy B.V.S., Madhuri C.R., and Sabitha G. Synthesis (2001) 1065
105. Kumar R.S., Nagarajan R., and Perumal P.T. Synthesis (2004) 949
106. Majumdar K.C., and Bhattacharyya T. Synth. Commun. 28 (1998) 2907
107. Arrault A., Guillaumet G., Leger J.-M., Jarry C., and Merour J.-Y. Synthesis (2002) 1879
108. Majumdar K.C., Ghosh S.K., and Biswas P. Monatsh. Chem. 131 (2000) 967
109. Majumdar K.C., Biswas P., and Ghosh S.K. Synth. Commun. 30 (2000) 4128
110. Traven V.F., Podkhalyuzina N.Ya., Vasilyev A.V., and Manaev A.V. Arkivoc 1 (2000) 931. usa.org/ark/ARKIVOC/arkivocarticles.asp
111. Marzano C., Chilin A., Baccichetti F., Bettio F., Guiotto A., Miolo G., and Bordin F. Eur. J. Med. Chem. 39 (2004) 411
112. Fossa P., Mosti L., Menozzi G., Marzano C., Baccichetti F., and Bordin F. Bioorg. Med. Chem. 10 (2002) 743
113. Fujita M., Egawa H., Chiba K., and Mastumoto J.-i. J. Heterocycl. Chem. 34 (1997) 1731
114. Majumdar K.C., Ghosh M., and Jana M. Synthesis (2002) 669
115. Gyul'budagyan L.V., Aleksanyan I.L., and Avetisyan A.A. Khim. Zh. Armen. 53 (2000) 51
116. Gyul'budagyan L.V., Aleksanyan I.L., and Avetisyan A.A. Chem. Abstr. 135 (2001) 33425
117. Dyachenko V.D., Krivokolysko S.G., and Litvinov V.P. Zh. Org. Khim. 34 (1998) 707
118. Dyachenko V.D., Krivokolysko S.G., and Litvinov V.P. Chem. Abstr. 130 (1999) 237447
119. Sharanin Ya.A., Goncharenko M.P., Shestopalov A.M., Litvinov V.P., and Turov A.V. Zh. Org. Khim. 27 (1991) 1996
120. Sharanin Ya.A., Goncharenko M.P., Shestopalov A.M., Litvinov V.P., and Turov A.V. Chem. Abstr. 116 (1992) 194117
121. Geies A.A., Bakhite E.A., and El-Kashef H.S. Pharmazie 53 (1998) 686
122. Bakhite E.A. J. Chem. Research, Synop. (2000) 500
123. Bakhite E.A. J. Chem. Research, Synop. (M) (2000) 1201
124. Bakhite E.A. J. Chinese Chem. Soc. 48 (2001) 1175
125. Bakhite E.A. Collect. Czech. Chem. Commun. 57 (1992) 2359
126. Bakhite E.A. Chem. Abstr. 118 (1993) 233986
127. Abdel Hafez A.A., Kamel El-Dean A., Hassan A.A., El-Kashef H.S., Rault S., and Robba M. J. Heterocycl. Chem. 33 (1996) 341
128. Kamel El-Dean A.M., Shaker R., Abo El-Hassan A.A., and Abdel Latif F.F. J. Chinese Chem. Soc. 51 (2004) 335
129. Mekheimer R.A., Aluned E.Kh., El-Fahham H.A., and Kamel L.H. Synthesis (2001) 97
130. Levendis D.C., Moffit J., Staskun B., and van Es T. J. Chem. Research, Synop. (1999) 614
131. Semenov V.P., Lobanov P.S., Gindin V.A., and Potekhin A.A. Khim. Geterotsikl. Soedin. 29 (1993) 1695
132. Semenov V.P., Lobanov P.S., Gindin V.A., and Potekhin A.A. Chem. Abstr. 122 (1995) 9903
133. White L.A., O'Neil P.M., Park B.K., and Storr R.C. Tetrahedron Lett. 36 (1995) 5983
134. Russell R.K., van Nievelt C.E., Rampulla R.A., Klaubert D.H., and Bell S.C. Synthesis (1992) 753
135. Gorlitzer K., Gabriel B., Frohberg P., Wobst I., Drnitkowski G., and Jomaa H. Pharmazie 56 (2004) 439
136. Deprets S., and Kirsch G. Arkivoc 3 (2002) 40. usa.org/ark/ARKIVOC/arkivocarticles.asp
137. Koruznjak J.D., Slade N., Zamola B., Pavelic K., and Karminski-Zamola G. Chem. Pharm. Bull. 50 (2002) 656
138. Luo J.-K., Kudo H., Federspiel R.F., and Casle R.N. J. Heterocycl. Chem. 32 (1995) 317
139. Luo J.-K., Federspiel R.F., and Casle R.N. J. Heterocycl. Chem. 32 (1995) 659
140. Al-Omran F., Abdel Khalik M.M., Al-Awadhi H., and Elnagdi M.H. Tetrahedron 52 (1996) 11915
141. Gupta M.C.L.N., and Darbarwar M. Indian J. Chem. 34B (1995) 432
142. Majumdar K.C., and Ghosh M. Tetrahedron 58 (2002) 10047
143. Jackson Y.A., Hepburn S.A., and Reynolds W.F. J. Chem. Soc., Perkin Trans. 1 (2001) 2237
144. Gomez-Monterrey I., Campiglia P., Lama T., La Colla P., Diurno M.V., Grieco P., and Novellino E. Arkivoc 5 (2004) 85. usa.org/ark/ARKIVOC/arkivocarticles.asp
145. Marzinzik A.L., and Rademacher P. Synthesis (1995) 1131
146. 051,880. Angibaud P.R., and Venet M.G. PCT Int. Appl. WO (2003)
147. Angibaud P.R., and Venet M.G. Chem. Abstr. 139 (2003) 69163
148. Isomae K., Morimoto S., Hasegawa H., Morita K., and Kamei J. Eur. J. Pharm. 465 (2003) 97
149. 059,122. Denny W.A., Wilson W.R., Ware D.C., Atwell G.J., Milbank J.B.J., and Stevenson R.J. PCT Int. Appl. WO (2002)
150. Denny W.A., Wilson W.R., Ware D.C., Atwell G.J., Milbank J.B.J., and Stevenson R.J. Chem. Abstr. 137 (2002) 149339
151. Peng H., Kim D.-I., Sarkaria J.N., Cho Y.-S., Abraham R.T., and Zalkow L.H. Bioorg. Med. Chem. 10 (2002) 167
152. 074,790. Smith C.D., and Lawrence D.S. PCT Int. Appl. WO (2001)
153. Smith C.D., and Lawrence D.S. Chem. Abstr. 135 (2001) 303910
154. Heidempergher F., Pevarello P., Pillan A., Pinciroli V., Torre A.D., Speciale C., Marconi M., Cini M., Toma S., Greco F., and Varasi M. Farmaco 54 (1999) 152
155. Ferlin M.G., Gatto B., Chiarelotto G., and Palumbo M. Bioorg. Med. Chem. 9 (2001) 1843
156. Ferlin M.G., Gatto B., Chiarelotto G., and Palumbo M. Bioorg. Med. Chem. 8 (2000) 1415
157. He L., Chang H.-X., Chou T.-C., Savaraj N., and Cheng C.C. Eur. J. Med. Chem. 38 (2003) 101
158. Caprio V., Guyen B., Opoku-Boahen Y., Mann J., Gowan S., Kelland L.M., Read M.A., and Neidle S. Bioorg. Med. Chem. Lett. 10 (2000) 2063
159. Ablordeppey S.Y., Fan P., Li S., Clark A.M., and Hufford C.D. Bioorg. Med. Chem. 10 (2002) 1337
160. Chen L.-L., Chen Y.-L., and Tzeng C.-C. Chinese Pharm. J. 55 (2003) 49
161. Chen Y.-L., Chen I.-L., Lu C.-M., Tzeng C.-C., Tsao L.-T., and Wang J.-P. Bioorg. Med. Chem. 11 (2003) 3921
162. Togawa S., Mano T., Yano S., Shinji J., and Togawa S. Jpn. Kokai Tokkyo Koho JP 240 (2001) 543
163. Mano T., Yano S., and Shinji J. Chem. Abstr. 135 (2001) 205568
164. Simsek R., Safak C., Erol K., Ataman S., Ulgen M., and Linden A. Amn.-Forsch. 53 (2003) 159
165. Simsek R., Safak C., Erol K., Ataman S., Ulgen M., and Linden A. Chem. Abstr. 139 (2003) 239639
166. Howard T.T., Lingerfelt B.M., Purnell B.L., Scott A.E., Price C.A., Townes H.M., McNulty L.A., Handl H.L., Summerville K., Hudson S.J., Bowen J.P., Kiakos K., Hartley J.A., and Lee M. Bioorg. Med. Chem. 10 (2002) 2941
167. Marco J.L., De los Rios C., Carreiras M.C., Banos J.E., Badia A., and Vivas N.M. Arch. Pharm. (Weinheim, Ger.) 335 (2002) 347
168. Marco J.L., De los Rios C., Carreiras M.C., Banos J.E., Badia A., and Vivas N.M. Chem. Abstr. 138 (2003) 265139
169. Gopal M., Shenoy S., and Doddamani L.S. J. Photochem. Photobiology B: Biology 72 (2003) 69
170. Denmark. Seek P., and Kirsch G. XVIII International Symposium on Medicinal Chemistry (ISMC2004) (15-19 August 2004) 349. http://www.ismc2004.dk/index.php/Main/10/0
171. Chen J., Deady L.W., Desneves J., Kaye A.J., Finlay G.J., Baguley B.C., and Denny W.A. Bioorg. Med. Chem 8 (2000) 2461
172. Gopal M., Shahabuddin M.S., and Inamdar S.R. Proc. Indian Acad. Sci. (Chem. Sci.) 114 (2002) 687