"Multi-component reactions: Emerging chemistry in drug discovery" 'from Xylocain to Crixivan'

Current Medicinal Chemistry

Volumn 10, Issue 1, 2003, Pages 51-80

  Hulme, Christopher ^a   Gore, Vijay ^a  

^a AMGEN INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRROLIDONE DERIVATIVE; 2(1H) QUINOXALINONE DERIVATIVE; ANTHRANILIC ACID DERIVATIVE; ANTIDEPRESSANT AGENT; BENZAZEPINE DERIVATIVE; BENZIMIDAZOLE DERIVATIVE; BENZODIAZEPINE DERIVATIVE; BENZOTHIAZEPINE DERIVATIVE; BLOOD CLOTTING FACTOR 10A INHIBITOR; BUPIVACAINE; CARBAPENEM DERIVATIVE; CEPHALOSPORIN DERIVATIVE; IMIDAZOLE; IMIDAZOLE DERIVATIVE; INDINAVIR; INDOLE DERIVATIVE; LIDOCAINE; MACROCYCLIC COMPOUND; NATURAL PRODUCT; NOCARDICIN A; NOCARDICINIC ACID DERIVATIVE; OXAZOLE DERIVATIVE; PENICILLIN DERIVATIVE; PIPERAZINEDIONE; PIPERIDONE DERIVATIVE; PRILOCAINE; PROTEIN TYROSINE PHOSPHATASE; PROTON PUMP INHIBITOR; PYRROCAINE; UNINDEXED DRUG;

ANTIBACTERIAL ACTIVITY; CHEMICAL REACTION; COMBINATORIAL CHEMISTRY; COMBINATORIAL LIBRARY; DNA TEMPLATE; DRUG RESEARCH; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; NONHUMAN; REACTION OPTIMIZATION; REVIEW; STRUCTURE ACTIVITY RELATION;

ANIMALS; CHEMISTRY; CYCLIZATION; HUMANS; INDICATORS AND REAGENTS; INDINAVIR; LIDOCAINE; PHARMACOLOGY;

EID: 0037238724     PISSN: 09298673     EISSN: None     Source Type: Journal    
DOI: 10.2174/0929867033368600     Document Type: Review

References (181)

1. Ugi, I. Angew. Chem. Int. Ed. Engl. 1962, 1, 8.
2. Ugi, I.; Steinbruckner, C. Chem Ber. 1961, 94, 734.
3. Ugi, I.; Domling, A.; Horl, W. Endeavor, 1994, 18, 115.
4. Ugi, I.; Steinbruckner, C. DE-B 1,1959, 103, 337
5. An excellent review of the fields describes these early suggestions: Domling, A.; Ugi, I. Angew. Chem. Int. Ed. 2000, 39, 3168.
6. Weber, L. Curr. Opin. Chem. Biol. 2000, 4, 295.
7. Hantzsch, A. Ber. Dtsch. Chem. Ges. 1890, 23, 1474.
8. Biginelli, P. Ber. Dtsch. Chem. Ges. 1890, 91, 349.
9. Biginelli, P. Ber. Dtsch. Chem. Ges. 1893, 26, 447.
10. Bucherer, H.T.; Fischbeck, H.T. J. Prakt. Chem. 1934, 140, 24.
11. Bergs, H. Ger. Patent 1929, 566 094.
12. Armstrong, R. W.; Brown, S. D.; Keating, T.A.; Tempest, P.A. In Combinatorial Chemistry. Synthesis and Application; Wilson, S. R.; Czarnik, A. W, Eds.; John Wiley: New York, 1997; pp. 153-190.
13. See histogram featured in Bienayme, H.; Hulme, C; Oddon, G.; Schmitt, P. Chem. Eur. J. 2000, 6, 3321.
14. Schreiber, S.L. Bioorg. Med. Chem. 1998, 6, 1127.
15. Mason, J.S.; Morize, I.; Menard, P.R.; Cheney, D.L.; Labaudiniere, R.L.; Hulme, C. J. Med. Chem. 1999, 42, 3251.
16. Freidinger, R. M.; Current Opinion in Chemical Biology 1999, 3, 395.
17. Patchett, A. A.; Nargund, R. P. Annual Reports in Medicinal Chemistry 2000, 35, 289.
18. Lin, J.H.; Ostovic, D.; Vacca, J.P. Pharmaceutical Biotechnology 1998, 11, 233.
19. Reider, P.J. Chimia, 1997, 51, 306.
20. Passerini, M. Gazz. Chim. Ital. 1921, 51, 126.
21. Passerini, M. Gazz. Chim. Ital. 1921, 51, 181.
22. Gautier, A. Ann. Chim. (Paris) 1869, 112, 316.
23. 50 < 10mg/kg (mouse, p.o. or s.c. administration)].
24. Note when dealing with low molecular weight isocyanides, it is advisable to wash all glassware in methanolic/HCl solutions to convert the reagent to its corresponding hydrated & non-pungent formamide.
25. Appel, R.; Kleistuck, R.; Ziehn, K.D Angew. Chem. Int. Ed. Engl. 1977, 10, 132.
26. Barton, D.H.R.; Bowles, T.; Husinec, S.; Forbes, J.E.; Llobera, A.; Porter, A.E.A.; Zard, S.Z. Tetrahedron Lett. 1988, 29, 3343.
27. O'Neil, I.A.; Baldwin, J.E. Synlett 1990, 603.
28. The majority are available from ACB blocks at www.ACBBLOCKS.com.
29. Keating, T.A.; Armstrong, R.W. J. Am. Chem. Soc. 1995, 117, 7842.
30. Moran, E. J.; Tellew, J.E.; Zhao, Z.; Armstrong, R.W. J Org. Chem. 1993, 58, 7848.
31. Armstrong, R.W.; Tellew, J.E.; Moran, E.J. J. Org. Chem. 1992, 57, 2208.
32. Semple, J.E.; Owens, T.D.; Nguyen, K.; Levy, O.E. Org. Lett. 2000, 2, 2769.
33. Semple, J.E.; Rowley, D.C.; Brunck, T.K.; Ripka, W.C. Bioorg. Med. Chem. Lett. 1997, 7, 315.
34. Otto, H.H.; Schirmeister, T. Chem. Rev. 1997, 97, 133.
35. Banfi, L.; Guanti, G.; Riva, R. Chem. Commun. 2000, 985.
36. Jones, W.; Tadesse, S.; Chenera, B.; Viswanadhan, V.; Hulme, C. A.C.S, 223nd, American Chemical Society Meeting & Exposition, April 2002, New Orleans.
37. Dunn, B.M. Structure and Function of the Aspartic Proteases: Genetics, Structures, and Mechanisms; Plenum Press: New York, 1991; Vol. 306, xviii, 585 pp.
38. Takahashi, K. Aspartic Proteinases: Structure, Function, Biology, and Biomedical Implications; Plenum Press: New York, 1995.2.
39. Lee, C.E.; Kick, E.K.; Ellman, J.A. J. Am. Chem. Soc. 1998, 120, 9735-47.
40. Vassar, R.; Bennett, B. D.; Babu-Khan, S.; Kahn, S.; Mendiaz, E. A.; Denis, P.; Teplow, D. B.; Ross, S.; Amarante, P.; Leoloff, R.; Luo, Y.; Fisher, S.; Fuller, J.; Edenson, S.; Lile, J.; Jarosinski, M. A.; Biere, A. L.; Curran, E.; Burgess, T.; Louis, J. -C.; Collins, F.; Treanor, J.; Rogers, G.; Citron, M. Science 1999, 286, 735.
41. Selkoe, D. Trends Cell Biol. 1998, 8, 447
42. Selkoe, D. Nature 1999, 399A, 23.
43. Sinha, S.; Lieberburg, I. Proc. Natl. Acad. Sci. USA 1999, 96, 11049.
44. Pearlman, R.S.; Smith K.M. J. Chem. Inf. Comput. Sci. 1999, 39, 28.
45. Zabrocki, J.; Smith, G.D.; Dunbar, J.B.; Iijima, H.; Marshall, G.R. J. Am. Chem. Soc. 1988, 110, 5875.
46. Yu, K-L.; Johnson, R.L. J. Org. Chem. 1987, 52, 2051.
47. Marshall, G.R.; Humblet, C.; Van Opdenbosch, N.; Zabrocki, J. In Peptides: Synthesis-Structure-Function; Proceedings of the Seventh American Peptide Symposium; Rich, D.H., Gross, E., Eds.; Pierce Chemical: Rockford, IL, 1981; pp 669-672.
48. Abell, A.D.; Foulds, G.J. J. Chem. Soc. Perkin Trans. 1 1997, 17, 2475.
49. Nixey, T.; Hulme, C. Tetrahedron Lett. 2002, in press.
50. Salvino, J.; Kumar, V.N.; Orton, E.; Airey, J.; Kiesow, T.; Crawford, K.; Rose, M.; Krolikowski, P.; Drew, M.; Engers, D.; Krolinkowski, D.; Herpin, T.; Gardyan, M.; McGeehan, G.; Labaudiniere, R. J. Comb. Chem. 2000, 2(6), 691.
51. Drew, M.; Orton, E.; Krolikowski, P.; Salvino, J.; Kumar, N.V. J. Comb. Chem. 2000, 2(1), 8.
52. Jones, W.; Overland, D.; Poppe, L.; Cardenas, J.; Pate, M.; Hulme, C. LabAutomation 2002, T002.
53. Noda, A.; Noda, H.; Imamura, T.; Ono, Y.; Morita, M.; Kai, N.; Mine, S.; Goto, S. Yakugaku Zasshi 1991, 111, 499.
54. Ager, I.R.; Barnes, A.C.; Danswan, G.W.; Hairsine, P.W.; Kay, P.D.; Matharu, S.S.; Miller, P.; Robson, P. J. Med. Chem. 1988, 31, 1098.
55. Campiani, G.; Cappelli, A.; Nacci, V.; Anzini, M.; Vomero, S.; Hamon, M.; Cagnotto, A.; Fracasso, C.; Uboldi, C.; Caccia, S.; Consolo, S.; Manninni, T. J. Med. Chem. 1997, 40, 3670.
56. Kobayashi, K.; Irisawa, S.; Matoba, T.; Matsumoto, T.; Yoneda, K.; Morikawa, O.; Konishi, H. Bull. Chem. Soc. Jpn. 2001, 74, 1109.
57. Bossio, R.; Marcaccini, S.; Pepino, R. Heterocycles 1986, 24, 2003.
58. Bossio, R.; Marcaccini, S.; Pepino, R. Tetrahedron Lett. 1986, 27, 4643.
59. Bossio, R.; Marcaccini, S.; Pepino, R. Heterocycles, 1986, 24, 2411.
60. Bossio, R.; Marcaccini, S.; Pepino, R.; Torroba, T.; Valle, G. Synthesis 1987, 1138.
61. Bossio, R.; Marcaccini, S.; Pepino, R. Liebigs Ann. Chem. 1991, 1107.
62. Ugi, I.; Steinbruckner, C.; DE-B 1,103,337, 1959.
63. Nakamura, M.; Inoue, J.; Yamada, T. Bioorg Med. Chem. Lett. 2000, 10, 2807.
64. Bossard, M.J.; Tomaszek, T.A.; Thomso, S.K.; Amegadzie, B.Y.; Hanings, C.R.; Jones, C.; Kurdyla, J.T.; McNulty, D.E.; Drake, F.H.; Gowen, M.; Levy, M.A. J. Biol. Chem. 1996, 271, 12517.
65. Katunuma, N.; Kominami, E. Rev. Physiol. Biochem. Pharmacol. 1987, 108, 1.
66. Wang, K.K.W.; Yuen, P.-W. Trends Pharmacol. Sci. 1994, 15, 412.
67. Floyd, C.D. Harnett, L.A.; Miller, A.; Patel, S.; Saroglou, L.; Whittaker, M. Synlett 1998, 637.
68. Burns, C.J.; Groneberg, R.D.; Salvino, J.M.; McGeehan, G.; Condon, S.M.; Morris, R.; Morrissette, M.; Mathew, R.; Darnbrough, S; Neuenschwander, K.; Scotese, A.; Djuric, S.W.; Ullrich, J.; Labaudiniere, R. Angew. Chem. 1998, 110, 3044; Angew. Chem. Int. Ed. Engl. 1998, 37, 2848.
69. Newton, R. C.; Decicco, C. P. J. Med. Chem. 1999, 42, 2295.
70. Cao, X.; Moran, E.J.; Siev, D.; Lio, A.; Ohashi, C.; Mjalli, A.M.M. Bioorg. Med. Chem Lett. 1995, 5, 2953.
71. Hunter, T. Curr. Opin. Cell Biol. 1989, 1, 1168.
72. Brown-Schimmer, S.; Johnson, K.A.; Hill, D.E.; Olefsky, J.M.; Bruskin, A.M. Cancer Res. 1992, 52, 478.
73. Woodford-Thomas, T.A.; Rhodes, J.D.; Dixon, J.E. J. Cell Biol. 1992, 117, 401.
74. Kenner, K.A.; Hill, D.E.; Olefsky, J.M.; Kusari, J. J. Biol. Chem. 1993, 268, 25455.
75. Zanke, B.; Squire, J.; Griesser, H.; Henry, M.; Suzuki, H.; Patterson, B.; Minden, M.; Mak, T.W. Leukemia 1994, 8, 236.
76. Hunter, D.H.; Sim, S.K. J. Am. Chem. Soc. 1969, 91, 2602.
77. Weber, L.; Wallbaum, S.; Broger, C.; Gubernator, K. Angew. Chem. Int. Ed. Engl. 1995, 34, 2280.
78. Simanek, E.E.; McGarvey, G.J.; Jablonski, J.A.; Wong, C.-H. Chem. Rev. 1998, 98, 833.
79. Bradley, H.; Fitzpatrick, G. Glass, W.K.; Kunz, H.; Murphy, P.V. Org. Lett. 2001, 3, 2629.
80. Nielsen, P. E.; Egholm, M. Peptide Nucleic Acids, Horizon Scientific: Wymondham 1999.
81. Maison, W.; Sclemminger, I.; Westerhoff, Ole; Martens, J. Bioorg. Med. Chem. Lett. 2000, 8, 1343.
82. Maison, W.; Schlemminger, I.; Westerhoff, O.; Martens, J. Bioorg. Chem. Lett. 1999, 9, 581.
83. Ugi, I.; Wischofer, E. Chem. Ber. 1962, 95, 136.
84. Isenring, H.P.; Hofheinz, W. Synthesis 1981, 385.
85. Hashimoto, M.; Komori, T.; Kamiya, T. J. Am. Chem. Soc. 1976, 98, 3023.
86. Harriman, G.C.B. Tetrahedron Lett. 1997, 38, 5591.
87. Hanusch-Kompa, C.; Ugi, I. Tetrahedron Lett. 1998, 39, 2725.
88. Short, K.M.; Mjalli, A.M.M. Tetrahedron Lett. 1997, 38, 359.
89. Hanusch-Kompe, C.; Ugi, I. Tetrahedron Lett. 1998, 39, 2725.
90. Hulme, C.; Jones W.J. unpublished results.
91. Zhang, J.; Jacobsen, A.; Rusche, J.R.; Herlihy, W. J. Org. Chem. 1999, 64, 1074.
92. Demharter, A.; Hoerl, W., Herdtweck, E.; Ugi, I. Angew. Chem. Int. Ed. Engl. 1996, 35, 173.
93. Ugi, I.; Goebel, M.; Gruber, B.; Heilingbrunner, M.; Heiss, B.; Hoerl, W.; Kern, O.; Starnecker, M. Tetrahedron 1996, 52, 11657.
94. Bienayme, H.; Bouzid, K. Angew. Chem. Int. Ed. 1998, 37, 2234.
95. Chen, J.J.; Golebiowski, A.; McClenaghan, J.; Klopfenstein, S.R. West, L. Tetrahedron Lett. 2001, 42, 2269.
96. Blackburn, C.; Guan, B.; Fleming, P.; Shiosaki, K.; Tsai, S. Tetrahedron Lett. 1998, 39, 3635.
97. Varma, R.S.; Kumar, D. Tetrahedron Lett. 1999, 40, 7665.
98. Varma, R.S. Heterocyclic Chemistry 1999, 36, 1565.
99. Mandair, G.S.; Light, M.; Russell, A.; Hursthouse, M.; Bradley, M. Tetrahedron Lett. 2002, 43, 4267.
100. Sun, X.; Janvier, P.; Zhao, G.; Bienayme, H.; Zhu, J. Org. Lett. 2001, 3, 877.
101. Janvier, P.; Sun, X.; Bienayme, H.; Zhu, J. J. Am. Chem. Soc. 2001, 124, 2560.
102. Zhao, G.; Sun, X.S.; Bienayme, H.; Zhu, J. J. Am. Chem. Soc. 2001, 123, 6700.
103. Fairlie, D.P.; Abbenante, G.; March, D.R. Curr. Med. Chem. 1995, 2, 654.
104. Palfreyman, M.G. Expert Opin. Invest. Drugs 1998, 1201.
105. Mitchison, T.J. Chem. Biol. 1994, 1, 3.
106. McDowell, R.S.; Blackburn, B.K.; Gadek, T.R.; McGee, L.R.; Rawson, T.; Reynolds, M.E.; Robarge, K.D.; Somers, T.C.; Thorsett, E.D.; Tischler, M.; Webb, R.R. and Venuti, M.C. J. Am. Chem. Soc. 1994, 116, 5077-5083.
107. Cho, N.S.; Song, K.Y.; Parkanyi, C. J. Heterocycl. Chem. 1989, 26, 1807.
108. Bunin, B.A.; Ellman, J.A. J. Am. Chem. Soc. 1992, 114, 10997.
109. Keating, T.A.; Armstrong, R.W. J. Am. Chem. Soc. 1996, 118, 2574. For earlier syntheses of 1,4-benzodiazepines
110. see Gates, M. J. Org. Chem. 1980, 45, 1675.
111. Uskokovic, M.; Iacobelli, J.; Wenner, W. J. Org. Chem. 1962, 27, 3606.
112. Keating, T.A.; Armstrong, R.W. J. Org. Chem. 1996, 61, 8935.
113. Hulme, C.; Tang, S-Y.; Burns, C. J.; Morize, I.; Labaudiniere, R. J. Org. Chem. 1998, 63, 8021.
114. Hulme, C.; Morrissette, M.; Volz, F.; Burns, C. Tetrahedron Lett. 1998, 39, 1113.
115. Hulme, C.; Peng, J.; Louridas, B.; Menard, P.; Krolikowski, P.; Kumar, N.V. Tetrahedron Lett., 1998, 39, 8047.
116. Note that MP-carbonate (Argonaut Technologies) was used to facilitate cyclization in the ketopiperazine series.
117. Ugi, I.; Zychlinski, A.V. Heterocycles 1998, 49, 29.
118. Nixey, T.; Tempest, P.; Hulme, C. Tetrahedron Lett. 2002, 43, 1637.
119. Hulme, C.; Ma, L.; Romano, J.; Cherrier, M.P.; Salvino, J.; Labaudiniere, R. Tetrahedron Lett. 2000, 41, 1889.
120. Keating, T.A.; Armstrong, R.W. J. Am. Chem. Soc. 1996, 118, 2574.
121. Mjalli, A.M.M. Sarshar, S. Baiga, T.J. Tetrahedron Lett. 1996, 37, 2943.
122. Miller, J.F.; Koch, K.; Piscopio, A.D. 1997, 214th ACS National Meeting, Las Vegas, NY, ORGN-232.
123. Lindhorst, T.; Bock, H.; Ugi, I. Tetrahedron 1999, 55, 7411.
124. Kennedy, A.L.; Fryer, A.M.; Josey, J.A. Org. Lett. 2002, 4, 1167.
125. Hulme, C.; Peng, J.; Morton, G.; Salvino, J.M.; Herpin, T.; Labaudiniere, R. Tetrahedron Lett. 1998, 39, 7227.
126. Flynn, D. L.; Zelle, R. E.; Grieco, P. A. J. Org. Chem. 1983, 48, 2424.
127. Plunkett, M.J.; Ellman, J.A. J. Org. Chem. 1995, 60, 6006.
128. Hulme, C.; Cherrier, M.P. Tetrahedron Lett. 1999, 40, 5295.
129. Kelder, J.; Grootenhuis, P.D.J.; Bayada, D.M.; Delbressine, L.P.C.; Ploemen, J-P. Pharmaceutical Research 1999, 16, 1514.
130. Hulme, C.; Ma, L.; Labaudiniere, R. Tetrahedron Lett. 2000, 41, 1509.
131. Szardenings, A.K.; Antonenko, V.; Campbell, D.A.; DeFrancisco, N.; Ida, S.; Shi, L.; Sharkov, N.; Tien, D.; Wang, Y.; Navre, M. J. Med. Chem. 1999, 42, 1348.
132. Hulme, C.; Ma, L.; Romano, J.; Morton, G.; Tang, S-Y.; Cherrier, M-P.; Choi, S.; Labaudiniere, R. Tetrahedron Lett. 2000, 41, 1883.
133. Ugi, I.; Steinbruckner, C. Chem. Ber. 1961, 94, 2802.
134. Keating, T. A.; Armstrong, R. W. J. Org. Chem. 1998, 63, 867-871.
135. Karabelas, K.; Lepisto, M.; Sjo, P. WO9932483-A1.
136. Miller, K. E.; Carpenter, J. F.; Brooks, R. R. Cardiovasc. Drugs Ther. 1998, 12(1), 83.
137. Busch, A. E.; Eigenberger, B.; Jurkiewicz, N. K.; Salata, J. J.; Pica, A.; Suessbrich, H.; Lang, F. Br. J. Pharmacol. 1998, 123(1), 23.
138. Edmunds, J. J.; Klutchko, S.; Hamby, J. M.; Bunker, A. M.; Connolly, C. J. C.; Winters, R. T.; Quin, J.; Sircar, I.; Hodges, J. C. J. Med. Chem. 1995, 38(19), 3759. For previous syntheses of hydantoins see:
139. Hanessian, S.; Yang, R-Y, Tetrahedron Lett. 1996, 37, 5835.
140. Short, K.M.; Ching, B.W.; Mjalli, A.M.M. Tetrahedron Lett. 1996, 37, 7489.
141. Dressman, B. A.; Spangle, L.A.; Kaldor, S.W.; Tetrahedron Lett. 1996, 37, 937.
142. Kim, S.W.; Ahn, S.Y.; Koh, J.S.; Lee, J.H.; Ro, S.; Cho, H.Y. Tetrahedron Lett. 1997, 38, 4603.
143. PS-tris-amine was purchased from Argonaut Technologies.
144. Tempest, P.; Kelly, M.; Hulme, C. Tetrahedron Lett. 2001, 42, 4959.
145. Pigini, M.; Bousquet, P.; Carotti, A.; Dontenwill, M.; Gianella, M.; Moriconi, R.; Piergentili, A.; Quaglia, W.; Tayebati, S.K.; Brasili, L.; Bioorg. Med. Chem. 1997, 5, 833.
146. Harfenist, M.; Heuser, D.J.; Joyner, C.T.; Batchelor, J.F.; White, H.L.; J. Med Chem. 1996, 39, 1857.
147. Jackson, H.C.; Griffin, I.J.; Nutt, D.J.; Br. J. Pharmacol. 1991, 104, 258.
148. Tibirica, E.; Feldman, J.; Mermet, C.; Gonon, F.; Bousquet, P. J. Pharmacol. 1987, 134, 1.
149. Gilbert, I.; Rees, D.C.; Richardson, R.S. Tetrahedron Lett. 1991, 32, 2277.
150. Jones, R.C.F.; Ward, G.J. Tetrahedron Lett. 1988, 29, 3853.
151. Zhao, Z.; Arnaiz, D.; Griedel, B.; Sakata, S.; Dallas, J.; Whitlow, M.; Trinh, L.; Post, J.; Liang, A.; Morrissey, M.; Shaw, K. Bioorg. Med. Chem. Lett. 2000, 10, 963.
152. Zarrinmayeh, H.; Nunes, A.; Ornstein, P.; Zimmerman, D.; Arnold, B.; Schober, D.; Gackenheimer, S.; Bruns, R.; Hipskind, P.; Britton, T.; Cantrell, B.; Gehlert, D. J. Med. Chem. 1998, 41, 2709.
153. Horn, J. Clin. Ther. 2000, 22, 266.
154. Nixey, T.; Tempest, P.; Hulme, C. Tetrahedron Lett. 2002, 43, 1637.
155. Astra AB WO9813368 (1998), WO9946260 (1999), WO9946264 (1999)
156. Masumoto, K. 118th Annual Meet. Pharm. Soc. Jpn. (March 31 - April 12, Kyoto), 1998, Abst. 01(XD) 10-1.
157. Tempest, P.; Ma, V.; Kelly, M.G.; Jones, W.J.; Hulme, C. Tetrahedron Lett. 2001, 4963.
158. Morales, G. A.; Corbett, J. W.; Degrado, W. F. J. Org. Chem. 1998, 63, 1172.
159. Phillips, G. B.; Wei, G-P Tetrahedron Lett. 1996, 37, 4887.
160. Tumelty, D.; Schwarz, M. K.; Cao, K.; Needels, M. C. Tetrahedron Lett. 1999, 40, 6185.
161. Stephensen, H.; Zaragoza, F. Tetrahedron Lett. 1999, 40, 5799.
162. Lee, J.; Gauthier, D.; Rivero, R. A. J. Org. Chem. 1999, 64, 3060.
163. Schwarz, M. K.; Tumelty, D.; Gallop, M.A. J. Org. Chem. 1999, 64, 2219.
164. Kiselyov, A.S.; Smith, L.; Tempest, P. Tetrahedron 1999, 55, 14813.
165. 3 modified Ugi reaction producing fused tetrazoles see, Bienayme, H. Tetrahedron Lett. 1998, 2735.
166. Nixey, T.; Kelly, M.; Hulme, C. Tetrahedron Lett. 2000, 41, 8729.
167. Nixey, T.; Kelly, M.; Semin, D.; Hulme, C. Tetrahedron Lett. 2002, 43, 3681.
168. Paulvannan, K. Tetrahedron Lett. 1999, 40, 1851.
169. Piscopio, A.D.; Miller, J.F.; Koch, K.; Tetrahedron 1999, 55, 8189.
170. Maison, W.; Lutzen, A.; Kosten, M.; Scleminger, I.; Westerhoff, O.; Saa, W.; Martens, J. J. Chem. Soc. Perkin Trans. 2000, 1, 1867.
171. Golebiowski, A.; Klopfenstein, S.R.; Shao, X.; Chen, J.J.; Colson, A-O.; Grieb, A.L.; Russell, A.F. Org. Lett. 2000, 2, 2615
172. Giannis, A.; Kolter, T. Angew. Chem. Int. Ed. Engl. 1993, 32, 1244.
173. van Leusen, A.M.; Wildeman, J.; Oldenziel, O.H. J. Org. Chem. 1977, 42, 1153.
174. Sisko, J.; Kassick, A.J.; Mellinger, M.; Filan, J.J.; Allen, A.; Olsen, M.A. J. Org. Chem. 2000, 65, 1516.
175. Lee, D.; Sello, J.K.; Schreiber, S.L. Org. Lett. 2000, 2, 709.
176. Rossen, K.; Sager, J.; DiMichele, L.M. Tetrahedron Lett. 1997, 38, 3183.
177. Mishani, E.; Dence, C.S.; McCarthy, T.J.; Welch, M.J. Tetrahedron Lett. 1996, 37, 319.
178. Kim, B.M.; Evans, B.E.; Gilbert, K.F.; Hanifin, C.M.; Vacca, J.P.; Michelson, S.R.; Darke, P.L.; Zugay, J.A.; Simini E.A. Bioorg. Med. Chem. Lett. 1995, 5, 2707.
179. Rossen, K.; Pye, P.J.; DiMichele, L.M.; Volante, R.P.; Reider, P.J. Tetrahedron Lett. 1998, 39, 6823.
180. Lack, O.; Weber, L. Chimia 1996, 50, 445.
181. Domling, A. Combinatorial Chemistry & High Throughput Screening, 1998, 1, 1.