Recent developments in isocyanide based multicomponent reactions in applied chemistry

Chemical Reviews

Volumn 106, Issue 1, 2006, Pages 17-89

  Dömling, Alexander ^a  

^a ABC Pharma   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; BIOCHEMISTRY; CATALYSTS; CONDENSATION REACTIONS; ENZYME INHIBITION; MOLECULAR DYNAMICS; ORGANIC COMPOUNDS; PHASE TRANSITIONS; PROTEINS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

CYCLOADDITIONS; ISOCYANIDE; MULTICOMPONENT REACTIONS (MCRS); NATURAL PRODUCT SYNTHESIS; PHASE TRANSFER CATALYSTS;

STEREOCHEMISTRY;

CYANIDE; ENZYME INHIBITOR; HETEROCYCLIC COMPOUND;

CHEMICAL MODEL; CHEMISTRY; COMBINATORIAL CHEMISTRY; DRUG DESIGN; METHODOLOGY; REVIEW; SYNTHESIS;

CHEMISTRY, PHARMACEUTICAL; COMBINATORIAL CHEMISTRY TECHNIQUES; CYANIDES; DRUG DESIGN; ENZYME INHIBITORS; HETEROCYCLIC COMPOUNDS; MODELS, CHEMICAL;

EID: 31544434530     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr0505728     Document Type: Review

References (328)

1. Multicomponent reactions; Zhu, J., Bienaymé, H., Eds.; Wiley: Weinheim, 2005.
2. Nishiyama, Y.; Katahira, C.; Sonoda, N. Tetrahedron Lett. 2004, 45, 8539.
3. Portlock, D. E.; Naskar, D.; West, L.; Ostaszewski, R.; Chen, J. J. Tetrahedron Lett. 2003, 44, 5121.
4. 2, RCHO, RCOR). However, less than 1000 boronic acids and isocyanides are available at the moment.
5. Bohacek, R. S.; McMartin, C.; Guida, W. C. Med. Chem. Rev. 1996, 16, 3.
6. Tietze, L. F. Chem. Rev. 1996, 96, 115.
7. Fayol, A.; Zhu, J. Org. Lett. 2005, 7, 239.
8. Beck, B.; Hess, S.; Dömling, A. Bioorg. Med. Chem. Lett. 2000, 10, 1701.
9. The author has created a database of more than 500 different scaffolds amenable by MCR reactions, which is growing daily. See also http:// www.organic-chemistry.org/Highlights/mcr.shtm.
10. Notable exceptions are the also formally divalent carbenes and carbon monoxide.
11. Bossio, R.; Marcaccini, S.; Pepino, R.; Marcos, C. F. J. Chem. Educ. 2000, 77, 382.
12. Ugi, I.; Werner, B.; Dömling, A. Targets Heterocycl. Syst. 2000, 4, 1.
13. Hulme, C.; Nixey, T. Curr. Opin. Drug Discovery Dev. 2003, 6, 921.
14. Ning, M.; Li, Z.; Zhao, W. Huaxue Jinzhan 2003, 15, 186.
15. Nerdinger, S.; Beck, B. Chemtracts 2003, 16, 233.
16. Zhu, J. Eur. J. Org. Chem. 2003, 7, 1133.
17. Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51.
18. Ugi, I. Pure Appl. Chem. 2001, 73, 187.
19. Bienaymé, H.; Schmitt, P. Actual. Chim. 2000, 9, 29.
20. Dömling, A. Curr. Opin. Chem. Biol. 2002, 6, 306.
21. Ugi, I.; Dömling, A. Comb. Chem. 2000, 287.
22. Ugi, I.; Dömling, A.; Werner, B. J. Heterocycl. Chem. 2000, 37, 647.
23. Dömling, A. Curr. Opin. Chem. Biol. 2000, 4, 318.
24. Sapi, J.; Laronze, J.-Y. ARKIVOC 2004, 208.
25. Orru, R. V. A.; de Greef, M. Synthesis 2003, 1471.
26. Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem.-Eur. J. 2000, 6, 3321.
27. Ugi, I.; Heck, S. Comb. Chem. High Throughput Screening 2001, 4, 1.
28. Dömling, A.; Ugi, I. Angew. Chem., Intl. Ed. 2000, 39, 3168.
29. Lockhoff, O.; Frappa, I. Comb. Chem. High Throughput Screening 2002, 5, 361.
30. Ramon, D., J.; Jus, M. Angew. Chem., Intl. Ed. 2005, 44, 1602.
31. van Leusen, D.; van Leusen, A., M. Org. React. (N. Y.) 2001, 57, 417.
32. Dyker, G. Org. Synth. Highlights IV 2000, 53.
33. Orru, R.; V., A.; de Greef, M. Synthesis 2003, 10, 1471.
34. Weber, L.; Dömling, A. PharmaChem 2004, 3, 31.
35. Dömling, A.; Ugi, I. Angew. Chem., Intl. Ed. 2000, 39, 3168.
36. Bock, H.; Ugi. J. Prakt. Chem. 1997, 339, 385.
37. Gassman, P. G.; Guggenheim, T. L. J. Am. Chem. Soc. 1982, 104, 5849.
38. Zhu, C.; Yuan, F.; Gu, W.; Pan, Y. Chem. Commun. 2003, 692.
39. Burdack, C.; Kolb, J. Production of chiral isocyanides that have a high structural diversity. WO 2003102532.
40. Ugi, I.; Kaufhold, G. Liebigs Ann. Chem. 1967, 709, 11.
41. Marquarding, D.; Hoffman, P.; Heitzer, H.; Ugi, I. J. Am. Chem. Soc. 1970, 92, 1969.
42. Kunz, H.; Sager, W. Angew. Chem., Intl. Ed. Engl. 1987, 26, 557.
43. Ross, G. F.; Herdtweck, E.; Ugi, I. Tetrahedron 2002, 58, 6127.
44. Zech, G.; Kunz, H. Chem.-Eur. J. 2004, 10, 4136.
45. Oertel, K.; Zech, G.; Kunz, H. Angew. Chem., Int. Ed. 2000, 39, 1431.
46. Drabik, J. M.; Achatz, J.; Ugi, I. Proc. Est. Acad. Sci., Chem. 2002 51, 156.
47. Dyker, G.; Breitenstein, K.; Henkel, G. Tetrahedron: Asymmetry 2002, 13, 1929.
48. Basso, A.; Banfi, L.; Riva, R.; Guanti, G. Tetrahedron Lett. 2004, 45, 587.
49. Basso, A.; Banfi, L.; Riva, R.; Guanti, G. J. Org. Chem. 2005, 70, 575.
50. Kelly, C. L.; Lawrie, K. W. M.; Morgan, P.; Willis, C. L. Tetrahedron Lett. 2000, 41, 8001.
51. Frey, R.; Galbraith, S., G.; Guelfi, S.; Lamberth, C.; Zeller, M. Synlett 2003, 1536.
52. Denmark, S.;, E.; Fan, Y. J. Am. Chem. Soc. 2003, 125, 7825.
53. Kusebauch, U.; Beck, B.; Messer, K.; Herdtweck, E.; Dömling, A. Org. Lett. 2003, 5, 4021.
54. Andreana, P. R.; Liu, C. C.; Schreiber, S. L. Org. Lett. 2004, 6, 4231.
55. Kern, O. T.; Motherwell, W. B. Chem. Commun. 2003, 2988.
56. Kern, O. T.; Motherwell, W. B. Chem. Commun. 2005, 1787.
57. Sun, X.; Janvier, P.; Zhao, G.; Bienaymé, H.; Zhu, J. Org. Lett. 2001, 3, 877.
58. Falomi, M.; Giacomelli, G.; Porcheddu, A.; Dettori, G. Ear. J. Org. Chem. 2000, 3217 and references cited therein.
59. Janvier, P.; Sun, X.; Bienaymé, H.; Zhu, J. J. Am. Chem. Soc. 2002, 124, 2560.
60. Gámez-Montanô, R.; González-Zamora, E.; Potier, P.; Zhu, J. Tetrahedron 2002, 58, 6351.
61. González-Zamora, E.; Fayol, A.; Bois-Choussy, M.; Chiaroni, A.; Zhu, J. Chem. Commun. 2001, 1684.
62. Fayol, A.; Zhu, J. Angew. Chem. 2002, 114, 3785;
63. Fayol, A.; Zhu, J. Angew. Chem., Int. Ed. 2002, 41, 3633.
64. Janvier, P.; H. Bienaymé, H.; Zhu, J. Angew. Chem. 2002, 114, 4467;
65. Janvier, P.; H. Bienaymé, H.; Zhu, J. Angew. Chem., Int. Ed. 2002, 41, 4291.
66. Janvier, P.; Bois-Choussy, M.; Bienaymé, H.; Zhu, J. Angew. Chem., Int. Ed. 2003, 42, 811.
67. Lobregat, V.; Alcaraz, G.; Bienaymé, H.; Vaultier, M. Chem. Commun. 2001, 817.
68. Bonne, D.; Dekhane, M.; Zhu, J. Org. Lett. 2004, 6, 4771.
69. Dömling, A.; Illgen, K. Synthesis 2005, 11, 662.
70. Kolb, J.; Beck, B.; Almstetter, M.; Heck, S,; Herdtweck, E.; Dömling A Mol. Diversity 2003, 6, 297.
71. Henkel, B.; Sax, M.; Dömling, A. Tetrahedron Lett. 2003, 44, 3679.
72. Henkel, B.; Westner, B.; Dömling, A. Synlett 2003, 2410.
73. 1 Kolb, J.; Beck, B.; Dömling, A. Tetrahedron Lett. 2002, 43, 6897.
74. Henkel, B.; Beck, B.; Westner, B.; Mejat, B.; Dömling, A. Tetrahedron Lett. 2003, 44, 8947.
75. Illgen, K.; Nerdinger, S.; Fuchs, T.; Friedrich, C.; Weber, L.; Herdtweck, E. Synlett 2004, 53.
76. Basso, A.; Banfi, L.; Guanti, G.; Riva, R.; Riu, A. Tetrahedron Lett. 2004, 45, 6109.
77. Mironov, M. A.; Ivantsova, M. N.; Mokrushin, V. S. Mol. Diversity 2003, 6, 193.
78. Pirrung, M. C.; Das Sarma, K. J. Am. Chem. Soc. 2004, 126, 444.
79. Hanusch-Kompa, C. Dissertation, Technische Universität München, 1997.
80. Pirrung, M. C.; Das, S. K. Synlett 2004, 1425.
81. Dömling, A. In Multicompoent Reactions; Zhu, J., Bienaymé, H., Eds.; Wiley-VCH: 2005.
82. Marcaccini, S.; Pepino, R.; Paoli, P.; Rossi, P.; Torroba, T. J. Chem. Res., Synop. 2001, 11, 465.
83. Illgen, K.; Nerdinger, S.; Behnke, D.; Friedrich, C. Org. Lett. 2005, 7, 39.
84. Carballares, S.; Espinosa, J. F. Org. Lett. 2005, 7, 2329.
85. Colin, T.; El Kaïm, L.; Gaultier, L.; Grimaud, L.; Gatay, L.; Michaut, V. Tetrahedron Lett. 2004, 45, 5611
86. Shabaani, A.; Bazgir, A.; Soleomani, K.; Bijanzahdeh, H. R. J. Fluorine Chem. 2002, 116, 93.
87. El Kaim, L.; Gaultier, L.; Grimaud, L.; Vieu, E. Tetrahedron Lett. 2004, 45, 8047
88. Ugi, I.; Fetzer, U. Chem. Ber. 1960, 94, 1116.
89. Chen, J. J.; Deshpande, S. V. Tetrahedron Lett. 2003, 44, 8873.
90. Schlemminger, I.; Janknecht, H.-H.; Maison, W.; Saak, W.; Martens, J. Tetrahedron Lett. 2000, 41, 7289.
91. Gedey, S.; Van der Eycken, J.; Fueloep, F. Org. Lett. 2002, 4, 1967.
92. Gedey, S.; Van der Eycken, J.; Fueloep, F. Lett. Org. Chem. 2004, 1, 215.
93. Gedey, S.; Vainiotalo, P.; Zupko, I.; de Witte, P. A. M.; Fueloep, F. J. Heterocycl. Chem. 2003, 40, 951.
94. Dinsmore, C. J.; Beshore, D. C. Tetrahedron 2002, 58, 3297.
95. Boehm, J. C.; Kingsbury, W. D. J. Org. Chem. 1986, 51, 2307.
96. Endo, A.; Yanagisawa, A.; Abe, M.; Tohma, S.; Kan, T.; Fukuyama, T. J. Am. Chem. Soc. 2002, 124, 6552.
97. (a) Hulme, C.; Morrissette, M. M.; Volz, F. A.; Burns, C. J. Tetrahedron Lett. 1998, 38, 1113.
98. (b) Hulme, C.; Peng, J.; Louridas, B.; Menard, P.; Krolikowski, P.; Kumar, N. V. Tetrahedron Lett. 1998, 38, 8047.
99. (a) Szardenings, A. K.; Burkoth, T. S.; Lu, H. H.; Tien, D. W.; Campbell, D. A. Tetrahedron 1997, 53, 6573.
100. (b) Szardenings, A. K.; Antonenko, V.; Campbell, D. A.; DeFrancisco, N.; Ida, S.; Shi, L.; Sharkov, N.; Tien, N.; Wang, Y.; Navre, M. J. Med. Chem. 1999, 42, 1384.
101. Zychlinsky, S.; Ugi, I. Heterocycles 1998, 49, 29.
102. Hulme, C.; Cherrier, M.-P. Tetrahedron Lett. 1999, 40, 5295.
103. Rossen, K.; Sager, J.; DiMichele, Tetrahedron Lett. 1997, 38, 3183.
104. (a) Marcaccini, S.; Pepino, R.; Pozo, M. A. Tetrahedron Lett. 2001, 42, 2727.
105. (b) Bossio, R.; Marcos, M. F.; Marcaccini, S.; Pepino, R. Tetrahedron Lett. 1997, 38, 2519.
106. (a) Ugi, I.; Demharter, A.; Hörl, W.; Schmid, T. Tetrahedron 1996, 52, 11657.
107. (b) Ugi, I.; Hörl, W.; Hanusch-Kompa, C.; Schmid, T.; Herdtweck, E. Heterocycles 1998, 47, 11657.
108. Marcaccini, S.; Pepino, R.; Pozo, M., C. Tetrahedron Lett. 2001, 42, 2727.
109. Cho, S.; Keum, G.; Kang, S. B.; Han, S.-Y.; Kim, Y. Mol. Diversity 2003, 6, 283.
110. Kennedy, A. L.; Fryer, A. M.; Josey, J. A. Org. Lett. 2002, 4, 1167.
111. Kim, Y. B.; Choi, E. H.; Keum, G.; Kang, S. B.; Lee, D. H.; Koh, H. Y.; Kim, Y. Org. Lett. 2001, 3, 4149.
112. Sung, K.; Chen, F.-L.; Chung, M.-J. Mol. Diversity 2003, 6, 213.
113. Zimmer, R.; Ziemer, A.; Gruner, M.; Brudgam, L; Hartl, H.; Reissig, H.-U. Synthesis 2001, 1649.
114. Kim, Y. B.; Park, S. J.; Keum, G.; Jang, M. S.; Kang, S. B.; Lee, D. H.; Kim, Y. Bull. Korean Chem. Soc. 2002, 23, 1277.
115. Godet, T.; Bonvin, Y.; Vincent, G.; Merle, D.; Thozet, A.; Ciufolini, M. Org. Lett. 2004, 6, 3281.
116. Marcaccini, S.; Pepino, R.; Pozo, M. C.; Basurto, S.; Garcia-Valverde, M.; Torroba, T. Tetrahedron Lett. 2004, 45, 3999.
117. Cheng, J.-F.; Chen, M.; Arrhenius, T.; Nadzan, A. Tetrahedron Lett. 2002, 43, 6293.
118. Faggi, C.; Garcia-Valverde, M.; Marcaccini, S.; Pepino, R.; Pozo, M. C. Synthesis 2003, 1553.
119. Marcos, C. F.; Marcaccini, S.; Pepino, R.; Polo, C.; Torroba, T. Synthesis 2003, 691.
120. Marcaccim, S.; Pepino, R.; Polo, C.; Pozo, M. C. Synthesis 2001, 85.
121. Ugi, I.; Böttner, E. Justus Liebigs Ann. Chem. 1963, 670, 74.
122. Diaz, J. L.; Miguel, M.; Lavilla, R. J. Org. Chem. 2004, 69, 3550.
123. Paulvannan, K. J. Org. Chem. 2004, 69, 1207.
124. Wright, D. L.; Robotham, C. V.; Aboud, K. Tetrahedron Lett. 2002, 43, 943.
125. Sello, J. K.; Andreana, P. R.; Lee, D.; Schreiber, S. L. Org. Lett. 2003, 5, 4125.
126. Dömling, A. Carr. Opin. Chem. Biol. 2002, 6, 306.
127. Oikawa, M.; Ikoma, M.; Sasaki, M. Tetrahedron Lett. 2005, 46, 415.
128. Akritopoulou-Zanze, I.; Gracias, V.; Moore, J. D.; Djuric, S. W. Tetrahedron Lett. 2004, 45, 3421.
129. Akritopoulou-Zanze, I.; Gracias, V.; Djuric, S. W. Tetrahedron Lett. 2004, 45, 8439.
130. Bon, R. S.; Hong, C.; Bouma, M. J.; Schmitz, R. F.; De Kanter, F. J. J.; Lutz, M.; Spek, A. L.; Orru, R. V. A. Org. Lett. 2003, 5, 3759.
131. Yoshida, H.; Fukushima, H.; Ohshita, J.; Kunai, A. Tetrahedron Lett. 2004, 45, 8659.
132. El Kaïm, L.; Gautier, L.; Grimaud, L.; Michaut, V. Synlett 2003, 1844.
133. Ancel, J. E.; El Kaïm, L.; Gadras, A.; Grimaud L.; Jana, N. K. Tetrahedron Lett. 2002, 43, 8319.
134. Behnke, D.; Taube, R.; Illgen, K.; Nerdinger, S.; Herdtweck, E. Synlett 2004, 688
135. Lindhorst, T.; Bock, H.; Ugi, I. Tetrahedron 1999, 55, 7741.
136. Rikimaru, K.; Yanagisawa, A.; Kann, T.; Fukuyama, T. Synlett 2004, 41.
137. Müller, S.; Neidlein, R. Helv. Chim. Acta 2002, 85, 2222.
138. Lengyel, I.; Cesare, V.; Taldone, T. Tetrahedron 2004, 60, 1107.
139. Banfi, L.; Basso, A.; Guanti, G.; Riva, R. Tetrahedron Lett. 2004, 45, 6637.
140. Marcaccini, S.; Pepino, R.; Torroba, T.; Miguel, D.; Garcia-Valverde, M. Tetrahedron Lett. 2002, 43, 8591.
141. Marcaccini, S.; Miguel, D.; Torroba, T.; Garcia-Valverde, M. J. Org. Chem. 2003, 68, 3315.
142. Nakamura, M.; Inoue, J.; Yamada, T. Bioorg. Med. Chem. Lett. 2000, 10, 2807.
143. Campian, E.; Lou, B.; Saneii, H. Tetrahedron Lett. 2002, 43, 8467.
144. Masdeu, C.; Diaz, J. L.; Miguel, M.; Jimenez, O.; Lavilla, R. Tetrahedron Lett. 2004, 45, 7907.
145. Oguri, H.; Schreiber, L. S. Org. Lett. 2005, 7, 47.
146. Keung, W.; Bakir, F.; Patron, A. P.; Rogers, D.; Priest, C. D.; Darmohusodo, V. Tetrahedron Lett. 2004, 45, 733.
147. Dömling, A. In Multicomponent reactions; Zhu, J., Bienaymé, H., Eds.; Wiley: Weinheim, 2005; p 76.
148. Dömling, A.; Herdtweck, Tetrahedron Lett., in press.
149. Gouge, V.; Jubault, P.; Quirion, J.-C. Tetrahedron Lett. 2004, 45, 773.
150. Gracias, V.; Moore, J. D.; Djuric, S. W. Tetrahedron Lett. 2004, 45, 417.
151. Xiang, Z.; Luo, T.; Lu, K.; Cui, J.; Shi, X.; Fathi, R.; Chen, J.; Yang, Z. Org. Lett. 2004, 6, 3155.
152. Beck, B.; Magnin-Lachaux, M.; Herdtweck, E.; Dömling, A. Org. Lett. 2001, 3, 2875.
153. Beck, B.; Picard, A.; Herdtweck, E.; Dömling, A. Org. Lett. 2004, 6, 39.
154. Krelaus, R.; Westermann, B. Tetrahedron Lett. 2004, 45, 5987.
155. Banfi, L.; Basso, A.; Guanti, G.; Riva, R. Tetrahedron Lett. 2003, 44, 7655.
156. Beck, B.; Larbig, G.; Mejat, B,; Magnin-Lachaux, M.; Picard, A.; Herdtweck, E.; Dömling, A. Org. Lett. 2003, 5, 1047.
157. Naskar, D.; Roy, A.; Seibel, W. L.; West, L.; Portlock, D. E. Tetrahedron Lett. 2003, 44, 6297.
158. Dömling, A.; Ugi, I. Angew. Chem., Intl. Ed. Engl. 1993, 32, 563.
159. Constabel, F.; Ugi, I. Tetrahedron 2001, 57, 5785.
160. Ugi, I.; Ebert B.; Hörl, W. Chemosphere 2001, 43, 75.
161. Gröbke, K.; Weber, L.; Mehlin, F. Synlett 1998, 661.
162. Ireland, S. M.; Tye, H.; Whittaker, M. Tetrahedron Lett. 2003, 44, 469.
163. Varma, R. S.; Kumar, D. Tetrahedron Lett. 1999, 40, 7665.
164. Chen, J. J.; Golebiowski, A.; McClenaghan, J.; Klopfenstein, S. R.; West, L. Tetrahedron Lett. 2001, 42, 2269.
165. Mandair, G. S.; Light, M.; Russell, A.; Hursthouse, M.; Bradley, M. Tetrahedron Lett. 2002, 43, 4267.
166. Lyon, Michael A.; Kercher, Timothy S. Org. Lett. 2004, 6, 4989,
167. Lu, Y.; Zhang, W. QSAR Comb. Sci. 2004, 23, 827.
168. Tempest, P.; Ma, V.; Thomas, S.; Hua, Z.; Kelly, M. G.; Hulme, C. Tetrahedron Lett. 2001, 42, 4959.
169. Tempest, P.; Pettus, L.; Gore, V.; Hulme, C. Tetrahedron Lett. 2003, 44, 1947.
170. Zhang, W.; Tempest, P. Tetrahedron Lett. 2004, 45, 6757.
171. Nixey, T.; Kelly, M.; Semin, D.; Hulme, C. Tetrahedron Lett. 2002, 43, 3681.
172. Nixey, T.; Tempest, P.; Hulme, C. Tetrahedron Lett. 2002, 43, 1637.
173. Hulme, C.; Ma, L.; Cherrier, M.-P.; Romano, J. J.; Morton, G.; Duquenne, C.; Salvino, J.; Labaudiniere, R. Tetrahedorn Lett. 2000, 41, 1883.
174. Golebiowski, A.; Jozwik, J.; Klopfenstein, S. R.; Colson, A.-O.; Grieb, A. L.; Russell, A. F.; Rastogi, V. L.; Diven, C. F.; Portlock, D. E.; Chen, J. J. J. Comb. Chem. 2002, 4, 584.
175. Golebiowski, A.; Klopfenstein, S. R.; Shan, X.; Chen, J. J.; Colson, A.-O.; Grieb, A. L.; Russell, A. F. Org. Lett. 2000, 2, 2615.
176. Faggi, C.; Marcaccini, S.; Pepino, R.; Pozo, M. C. Synthesis 2002, 18, 2756.
177. Cuny, G.; Bois-Choussy, M.; Zhu, J. J. Am. Chem. Soc. 2004, 126, 14475.
178. Marcaccini, S.; Miliciani, M.; Pepino, R. Tetrahedron Lett. 2005, 46, 711.
179. Kennedy, A. L.; Fryer, A. M.; Josey, J. A. Org. Lett. 2002, 4, 1167.
180. Tempest, P.; Ma, V.; Kelly, M. G.; Jones, W.; Hulme, C. Tetrahedron Lett. 2001, 42, 4963.
181. Umkehrer, M.; Kolb, J.; Burdack, C.; Ross, G.; Hiller, W. Tetrahedron Lett. 2004, 45, 6421.
182. Cristau, P.; Vors, J.-P.; Zhu, J. Org. Lett. 2001, 3, 4079.
183. Cristau, P.; Vors, J.-P.; Zhu, J. Tetrahedron 2003, 59, 7859.
184. Cristau, P.; Vors, J.-P.; Zhu, J. Tetrahedron Lett. 2003, 44, 5575.
185. Winterfeldt, E.; Schumann, D.; Dillinger, H. J. Chem. Ber. 1969, 102, 1656.
186. Yavari, I.; Adib, M.; Sayahi, M. H. J. Chem. Soc., Perkin Trans. 1 2002, 2343.
187. Nair, V.; Vinod, A. U. Chem. Commun. 2000, 1019
188. Yadav, J. S.; Reddy, S. B. V.; Shubashree, S.; Shadiv, K.; Naidu, J. J. Synthesis 2004, 2376.
189. Nair, V.; Vinod, A. U. J. Org. Chem. 2001, 66,4427.
190. Nair, V.; Vinod, A. U.; Nair, J. S.; Sreekanth, A. R.; Rath, N. P. Tetrahedron Lett. 2000, 41, 6675.
191. Nair, V.; Mathen, J. S.; Vinod, A. U.; Varma, R. L. Chem. Lett. 2001, 738.
192. Nair, V.; Vinod, A. U.; Ramesh, R.; Menon, R. S.; Varma, R. L.; Mathew, S.; Chiaroni, A. Heterocycles 2002, 58, 147.
193. Baharfar, R.; Hosseini, J. J. Chem. Res., Synop. 2003, 616.
194. Shaabani, A.; Teimouri, M., B.; Arab-Ameri, S. Tetrahedron Lett. 2004, 45, 8409.
195. Yavari, I.; Djahaniani, H.; Nasiri, F. Tetrahedron Lett. 2004, 45, 7099.
196. Shaabani, A.; Teimouri, M. B.; Bijanzadeh, H. R. J. Chem. Res., Synop. 2002, 381.
197. Yavari, I.; Nasiri, F.; Moradi, L.; Djahaniani, H. Tetrahedron 2003, 59, 9409.
198. Shaabani, A.; Teimouri, M., B.; Bazgir, A.; Bijanzadeh, H. R. Mol. Diversity 2003, 6, 199.
199. Shaabani, A.; Teimouri, M. B.; Bijanzadeh, H. R. J. Chem. Res., Synop. 2003, 578.
200. Shaabani, A.; Teimouri, M. B.; Bijanzadeh, H. R. Tetrahedron Lett. 2002, 43, 9151.
201. Shaabani, A.; Teimouri, M. B. J. Chem. Res., Synop. 2002, 433.
202. Nair, V.; Menon, R. S.; Vinod, A. U.; Viji, S. Tetrahedron Lett. 2002, 43, 2293.
203. Shaabani, A.; Teimouri, M. B.; Bager, M. J. Chem. Res., Synop. 2003, 732.
204. Shaabani, A.; Teimouri, M. B.; Bager, M.; Bijanzadeh, H. R. Monatsh. Chem. 2004, 135, 589.
205. Shurov, S. N. Chem. Heterocycl. Compd. 2002, 38, 1529.
206. The earliest report of a C-nucleophile is: Ugi, I.; Betz, W.; Offermann, K. The tropylium ion as α-addition partner of isonitriles. Ber. 1964, 97, 3008.
207. Kobayashi, K.; Takagoshi, K.; Kondo, S.; Morikawa, O.; Konishi, H. Bull. Chem. Soc. Jpn. 2004, 77, 553.
208. Mironov, M. A.; Mokrushin, V. S.; Maltsev, S. S. Synlett 2003, 943.
209. Kamijo, S.; Yamamoto, Y. J. Am. Chem. Soc. 2002, 124, 11940.
210. Cao, C.; Shi, Y.; Odom, A. L. J. Am. Chem. Soc. 2003, 125, 2880.
211. Salustre, C. G.; Whitby, R. J.; Furber, M. Angew. Chem., Intl. Ed. 2000, 39, 4156.
212. Salustre, C. G.; Whitby, R. J.; Furber, M. Tetrahedron Lett. 2001, 42, 6191.
213. Onitsuka, K.; Suzuki, S.; Takahashi, S. Tetrahedron Lett. 2002, 43, 6197.
214. Kishore, K.; Tetala, R.; Whitby, R. J.; Light, M. E.; Hurtshouse, M. B. Tetrahedron Lett. 2004, 45, 6991.
215. Saluste, G. C.; Crampler, S.; Furber, M.; Whitby, R. J. Tetrahedron Lett. 2004, 45, 6995.
216. Oshita, M.; Yamashita, K.; Tobisu, M.; Chatani, N. J. Am. Chem. Soc. 2005, 127, 761.
217. Wang, L.; Woods, K. W.; Li, Q.; Barr, K. J.; McCroskey, R. W.; Hannick, S. M.; Gherke, L.; Credo, R. B.; Hai, Y.-H.; Marsh, K.; Warner, R.; Lee, J. Y.; Zielinski-Mozng, N.; Frost, D.; Rosenberg, S. H.; Sham, H. L. J. Med. Chem. 2002, 45, 1697.
218. van Leusen; van Leusen. Org. React. 2003, 7.
219. Sisko, J.; Mellinger, M. Pure Appl. Chem. 2002, 74, 1349.
220. Sisko, J.; Kassick, A. J.; Mellinger, M.; Filan, J. J.; Allen, A.; Olsen, M. A. J. Org. Chem. 2000, 65, 1516.
221. Several companies meanwhile provide hundreds of substituted Tosmics; see, for example, www.synthatex.com or www.jwpharmiab.com.
222. Dombroski, Mark A.; Letavic, Michael A.; McClure, Kim F. U. S. Pat. Appl. Publ. (2004), US 2004092547.
223. Dombroski, M. A.; Letavic, M. A.; McClure, K. F. Preparation of 5-(phenylheteroaryl)-1,3-dihydro-2-benziniidazolone MAP kinase inhibitors as anti-inflammatory agents. 2002, WO 2002072576.
224. Hulme, C. In Multicomponent reactions; Zhu, J., Bienaymé, H., Eds.; Wiley: Weinheim, 2005; p 328.
225. Bräuer, S.; Ahmstetter, M.; Antuch, W.; Behnke, D.; Taube, R.; Furer, P.; Hess, S. J. Comb. Chem. 2005, 7, 218.
226. Shoda, M.; Harada, T.; Kogami, Y.; Tsujita, R.; Akashi, H.; Kouji, H.; Stahura, F. L.; Xue, L.; Bajorath, J. J. Med. Chem. 2004, 47, 4286.
227. Guery, S.; Schmitt, M.; Bourguignon, J.-J. Synlett 2002, 2003.
228. Giblin, G. M. P.; Hall, A.; Lewell, X. Q.; Miller, N. D. Preparation of 3-(imidazol-1-yI)benzoic acid derivatives for the treatment of conditions mediated by the action of PGE2 at EP1 receptors. WO 2004083185.
229. Armour, D. R.; Bell, A. S.; Edwards, P. J.; Ellis, D.; Hepworth, D.; Lewis, M. L.; Smith, C. R. Preparation of heterocycly1carboxamides as oxytocin inhibitors. WO 2004020414.
230. Borthwick, A. D.; Hatley, R. J.; Hickey, D. M. B.; Liddle, J.; Livermore, D. G. H.; Mason, A. M.; Miller, N. D.; Nerozzi, F.; Sollis, S. L.; Szardenings, A. K.; Wyatt, P. G. Preparation of substituted diketopiperazines as oxytocin antagonists. WO 2003053443.
231. Costantino, G.; Marinozzi, M.; Camaioni, E.; Natalini, B.; Sarichelou, I.; Micheli, F.; Cavanni, P.; Faedo, S.; Noe, C.; Moroni, F.; Pellicciari, R. Farmaco 2004, 59, 93.
232. Nishizawa, R.; Takaoka, Y.; Shibayama, S. Preparation of nitrogen-containing heterocyclic derivatives as chemokine receptor CCR5 antagonists and drugs containing the same as the active ingredient. WO 2004080966.
233. Gerlach, M.; Maul, C. Preparation of imidazopyridineamines and analogs as analgesics. WO 2001027119
234. 28 Barker, M. D.; Demaine, D. A.; House, D.; Inglis, G. G. A.; Johnston, M. J.; Jones, H. T.; Macdonald, S. J. F.; Mclay, I. M.; Shanahan, S.; Skone, P. A.; Vinader, M. V. Preparation of heterocycle-substituted N-benzoxazinylpropanamides as glucocorticoid receptor binders and agonists for the treatment of inflammatory, allergic and skin diseases. WO 2004071389.
235. Hulme, C. In Multicomponent reactions; Zhu, J., Bienaymé, H., Eds.; Wiley: Weinheim, 2005; p 333.
236. Musonda, C. C.; Taylor, D.; Lehman, J.; Gut, J.; Rosenthal, P. J.; Chibale, K. Bioorg. Med. Chem. Lett. 2004, 14, 3901.
237. Chapman, T. M.; Davies, I. G.; Gu, B.; Block, T. M.; Scopes, D. I. C.; Hay, P. A.; Courtney, S. M.; McNeill, L. A.; Schofield, C. J.; Davis, B. G. J. Am. Chem. Soc. 2005, 127, 506.
238. Nerdinger, S.; Fuchs, T.; Illgen, K.; Eckl, R. Aryl amides that inhibit factor Xa activity. WO 2002068390.
239. Weber, L.; Fuchs, T.; Illgen, K.; Dömling, A.; Cappi, M. Compounds that inhibit tryptase activity. WO 200114320.
240. Sheehan, S. M.; Masters, J. J.; Wiley, M. R.; Young, S. C.; Liebeschuetz, J. W.; Jones, S. D.; Murray, C. W.; Franciskovich, J. B.; Engel, D. B.; Weber, W. W.; Marimuthu, J.; Kyle, J. A.; Smallwood, J. K.; Farmen, M. W.; Smith, G. F. Bioorg. Med. Chem. Lett. 2003, 13, 2255.
241. Alig, L.; Groebke, Z. K.; Obst, U. Preparation of water-soluble phenylglycine derivatives as pharmaceuticals. WO 2003066588.
242. Groebke Zbinden, K.; Banner, D. W.; Ackermann, J.; D'Arcy, A.; Kirchhofer, D.; Ji, Y.-H.; Tschopp, T. B.; Wallbaum, S.; Weber, L. Bioorg. Med. Chem. Lett. 2005, 15, 817.
243. Staveski, M. M.; Sneddon, S. F. Preparation of (α-acyloxyacetamides as kallikrein and urokinase inhibitors. WO 2003101941.
244. Lin, X. P.; Wenwei, L.; Xiaomin, Z. Synthesis 2002, 1017.
245. Ugi, I.; Dömling, A.; Gruber, B.; Heilingbrunner, M.; Heiss, C.; Hörl, W. Formale Unterstützung bei Multikomponentenreaktionen-Automatisierung der Synthesechemie. In Software-Entwicklung in der Chemie; R. Moll (Hrsg.), Frankfurt: Gesellschaft Deutscher Chemiker, 1995; pp 113-128 (Tagungsband zu GDCh-Workshop 16.-18.11.1994).
246. Rossen, K.; Sager, J.; DiMichele, L. M. Tetrahedron Lett. 1997, 38, 3183.
247. Yehia, N. A. M.; Antuch, W.; Beck, B.; Hess, S.; Schauer-Vukasinovic, V.; Almstetter, M.; Furer, P.; Herdtweck, E.; Domling, A. Bioorg. Med. Chem. Lett. 2004, 14, 3121.
248. Banfi, L.; Guanti, G.; Riva, R. Chem. Commun. 2000, 985.
249. Semple, E.; Owens, T. D.; Nguyen, K.; Levy, O. E. Org. Lett. 2000, 2, 2769.
250. Banfi, L.; Guanti, G.; Riva, R.; Basso, A.; Calcagno, E. Tetrahedron Lett. 2002, 43, 4067.
251. Banfi, L.; Basso, A.; Guanti, G.; Riva, R. Mol. Diversity 2003, 6, 227.
252. Cuny, G.; Gamez-Montano, R.; Zhu, J. Tetrahedron 2004, 60,4879.
253. Nixey, T.; Hulme, C. Tetrahedron Lett. 2002, 43, 6833.
254. Neidlein, R. Arch. Pharm. 1966, 299, 603.
255. Oaksmith, J. M.; Peters, U.; Ganem, B. J. Am. Chem. Soc. 2004, 126, 13606.
256. Floyd, C. D.; Harnett, L. A.; Miller, A.; Patel, S.; Saroglou, L.; Whittaker, M. Synlett 1996, 637.
257. Thormann, M.; Almstetter, M. Method of preparation of bioisosteres of actinonin of interest as metalloproteinase inhibitors. WO 2004099124.
258. Nakamura, M.; Yamaguchi, M.; Sakai, O.; Inoue, J. Bioorg. Med. Chem. Lett. 2003, 11, 1371.
259. Lockhoff, O.; Frappa, I. Comb. High Throughput Screening 2002, 5, 361.
260. Liu, L.; Li, C. P.; Cochran, S.; Ferro, V. Bioorg. Med. Chem. Lett. 2004, 14, 2221.
261. (a) Li, Y.; Zhang, X.; Chu, S.; Yu, K.; Guan, H. Carbohydr. Res. 2004, 339, 873.
262. (b) Zhang, X. R.; Li, Y. X.; Chu, S. D.; Yu, K. Y.; Guan, H. S. Chin. Chem. Lett. 2003, 14, 1130.
263. Bradley, H.; Fitzpatrick, G.; Glass, W. K.; Kunz, H.; Murphy, P. V. Org. Lett. 2001, 3, 2629.
264. Parks, D. J.; LaFrance, L. V.; Calvo, R. R.; Milkiewicz, K. L.; Gupta, V.; Lattanze, J.; Ramachandren, K.; Carver, T. E.; Petrella, E. C.; Cummings, M. D.; Maguire, D.; Grasberger, B. L.; Lu, T. Bioorg. Med. Chem. Lett. 2005, 15, 765.
265. Grasberger, B. L.; Lu, T.; Schubert, C.; Parks, D. J.; Carver, T. E.; Koblish, H. K.; Cummings, M. D.; LaFrance, L. V.; Milkiewicz, K. L.; Calvo, R. R.; Maguire, D.; Lattanze, J.; Franks, C. F.; Zhao, S.; Ramachandren, K.; Bylebyl, G. R.; Zhang, M.; Marithey, C. L.; Petrella, E. C.; Pantoliano, M. W.; Deckman, I. C.; Spurlino, J. C.; Maroney, A. C.; Tomczuk, B. E.; Molloy, C. J.; Bone, R. F. J. Med. Chem. 2005, 48, 909.
266. Suda, A.; Ohta, A.; Sudoh, M.; Tsukuda, T.; Shimma, N. Heterocycles 2001, 55, 1023.
267. Owens, T. D.; Araldi, G.-L.; Nutt, R. F.; Semple, J. E. Tetrahedron Lett. 2001, 42, 6271.
268. Owens, Timothy D.; Semple, J. Edward Org. Lett. 2001, 3, 3301.
269. Endo, A.; Yanagisawa, A.; Abe, M.; Tohma, S.; Kan, T.; Fukuyama, T. J. Am. Chem. Soc. 2002, 124, 6552.
270. Mori, K.; Rikimaru, K.; Kan, T.; Fukuyama, T. Org. Lett. 2004, 6, 3095.
271. Rikimaru, K.; Mori, K.; Kan, T.; Fukuyama, T. Chem. Commun. 2005, 394.
272. Dömling, A.; Beck, B. Org. Lett., submitted.
273. Alla, S.; Choi, S.-Y.; Condeiu, C.; Dhanoa, D.; Difranco, E.; Krokhina, G.; Li, K.; Thiagarajan, B.; Zhang, W.-C. Preparation of amino acid derivatives as pharmaceuticals. W02003010130.
274. Kazmaier, U.; Hebach, C. Synlett 2003, 1591.
275. Yamada, T.; Ichino, T.; Hanyu, M.; Ninomiya, D.; Yanagihara, R.; Miyazawa, T.; Murashima, T. Org. Biomol. Chem. 2004, 2, 2335.
276. Hanyu, M.; Murashima, T.; Miyazawa; Yamada, T. Tetrahedron Lett. 2004, 45, 8871.
277. Bayer, T.; Riemer, C.; Kessler, H. J. Peptide Sci. 2001, 7, 250.
278. Costa, S. P.; Maia, H. L.; Pereira-Lima, S. M. Org. Biomol. Chem. 2003, 1, 1475.
279. Jiang, W.-Q.; Costa S. P. G.; Maia, H. L. S. Org. Biomol. Chem. 2003, 1, 3804.
280. Hebach, C.; Kazmaier, U. Chem. Commun. 2003, 5, 596.
281. Dömling, A. Nucleotides Nucleotides 1998, 17, 1667.
282. Dömling, A.; Chi, K.-Z.; Barrère, M. Bioorg. Med. Chem. Lett. 1999, 9, 2871
283. Maison, W.; Schlemminger, I.; Westerhoff, O.; Martens, J. Bioorg. Med. Chem. 2000, 8, 1343.
284. Baldoli, C.; Giannini, C.; Licandro, E.; Maiorana, S.; Zinzalla, G. Synlett 2004, 1044.
285. Baldoli, C.; Maiorana, S.; Licandro, E.; Zinzalla, G.; Perdicchia, D. Org. Lett. 2002, 4, 4341.
286. Xu, P.; Zhang, T.; Wang, W.; Zou, X.; Zhang, X.; Fu, Y. Synthesis 2003, 8, 1171.
287. Shibata, N.; Das, B. K.; Takeuchi, Y. Perkin 1 2000, 24, 4234.
288. Kvumar Das, B.; Shibata, N.; Takeuchi, Y. J. Chem. Soc., Perkin Trans. I 2002, 197.
289. Zakrzewski, J.; Jezierska, J.; Hupko, J. Org. Lett. 2004, 6, 695.
290. Some patents of Ivar Ugi involving IMCR based polymers: Ugi, I.; Bonin, W. v. Polyester amides. 1963, BE 630577 19630801.
291. Ugi, I. Polyisonitriles. 1963, DE 1158500 19631205.
292. Ugi, I. Polyamides. 1964, F 1353227 19640221.
293. Bonin, W. v.; Ugi, I. Cross-linked carboxyl-containing copolymers. 1964, BE 635759 19640203.
294. Bonin, W. v.; Fetzner, U.; Ugi, I. Heat-stable acrylic polymers. 1964, DE 1181422 19641112.
295. Ugi, I. Alkyl-substituted phenylene diisonitriles. U. S. 1972, US 3636036.
296. de Nooy, A., E.; Capitani, D.; Masci, G.; Crescenzi, V. Biomacromolecules 2000, 1, 259.
297. Crescenzi, V.; Francescangeh, A.; Renier, D.; Bellim, D. Biopolymers 2002, 64, 86.
298. Crescenzi, S. V.; Francescangeli, A.; Segre, A. L.; Capitani, D.; Mannina, L.; Renier, D.; Bellini, D. Macromol. Biosci. 2002, 2, 272.
299. de Nooy, A. E. J.; Rori, V.; Masci, G.; Dentini, M.; Crescenzi, V. Carbohydr. Res. 2000, 324, 116.
300. Bu, H.; Kjoniksen, A.-L.; Knudsen, K. D.; Nystroem, B. Biomacromolecules 2004, 5, 1470.
301. Crescenzi, V.; Francescangeli, A.; Capitani, D.; Mannina, L.; Renier, D.; Bellini, D. Carbohydr. Polym. 2003, 53, 311.
302. Robotham, C. V.; Baker, C.; Cuevas, B.; Abboud, K.; Wright D. L. Mol. Diversity 2003, 6, 237.
303. Brahmachary, E.; Ling, F. H.; Svec, F.; Freehet, J. M. J. J. Comb. Chem. 2003, 5, 441.
304. Hulme, C.; Peng, J.; Morton, G.; Salvino, J. M.; Hrpin, T.; Labaudiniere, R. Tetrahedron Lett. 1998, 39, 7227.
305. Kulkarni, B. A.; Ganesan, A. Tetrahedron Lett. 1999, 40, 5633.
306. Barrett, A. G. M.; Cramp, S. M.; Hennessy, A. K.; Procopiou, P. A.; Roberts, R. S. Org. Lett. 2001, 3, 271.
307. Gravel, M.; Berube, C. D.; Hall, D. G. J. Comb. Chem. 2000, 2, 228.
308. Kim, S. W.; Bauer, S. M.; Armstrong, R. W. Tetrahedron Lett. 1998, 39, 6993.
309. Tempest, P. A.; Brown, S. D.; Armstrong, R. W. Angew. Chem., Intl. Ed. Engl. 1996, 35, 640.
310. Piscopio, A. D.; Miller, J. F.; Koch, K. Tetrahedron 1999, 55, 8189.
311. Hulme, C.; Ma, L.; Kumar, N. V.; Krolikowski, P. H.; Allen, A. C.; Labaudiniere, R. Tetrahedron Lett. 2000, 41, 1509.
312. Oikawa, M.; Ikoma, M.; Sasaki, M. Tetrahedron Lett. 2004, 45, 2371.
313. Henkel, B.; Sax, M.; Dömling, A. Tetrahedron Lett. 2003, 44, 7015.
314. Henkel, B.; Weber, L. Synlett 2002, 1877.
315. Chen, J. Process for making and using isocyanide group-containing resins via the formylation of amino acid moiety-containing polymers followed by their dehydration. PCT Int. Appl. 2001, WO 2001058861.
316. Chen, J., J.; Golebiowski, A.; Klopfenstein, S., R.; West, L. Tetrahedron Lett. 2002, 43, 4083.
317. Ley, S. V.; Taylor, S. J. Bioorg. Med Chem. Lett. 2002, 12, 1813.
318. Ziegler, T.; Gerling, S.; Lang, M. Angew Chem., Intl. Ed. 2000, 39, 2109.
319. Launay, D.; Booth, S.; Clemens, I.; Merritt, A.; Bradley, M. Tetrahedron Lett. 2002, 43, 7201.
320. Tye, H.; Whittaker, M. Org. Biomol. Chem. 2004, 2, 813.
321. Mitchell, M. C.; Spikmans, V.; de Mello, A. I Analyst 2001, 126, 24.
322. Mitchell, M. C.; Spikmans, V.; Manz, A.; de Mello, A. J. J. Chem. Soc., Perkin Trans. 1 2001, 514.
323. Liu, X.-C.; Clark, D. S.; Dordick, I S. Biotechnol. Bioeng. 2000, 69, 457.
324. Ostazewski, R.; Portlock, D. E.; Fryszkowska, A.; Jeziorska, K. Pure Appl. Chem. 2003, 75, 413.
325. Williams, L. Color encoded parallel synthesis. Proceedings of ECSOC-3, [and] Proceedings of ECSOC-4, Sept. 1-30, 1999 and 2000, p 200. http:// pages.unibas.ch/mdpi/ecsoc-3/b000llb000l.htm.
326. March, J. Advanced Organic Chemistry; Wiley-Interscience: New York, 1985.
327. Ugi, I.; Steinbrückner, C. Chem. Ber. 1961, 94, 734.
328. Fewell, S. W.; Smith, C. M.; Lyon, M. M.; Dumitrescu, T. P.; Wipf, P.; Day, B. W.; Brodsky, J. L. J. Biol. Chem. 2004, 279, 51131.