Synthesis of rigid hydrophobic tetrazoles using an Ugi multi-component heterocyclic condensation

Tetrahedron Letters

Volumn 39, Issue 18, 1998, Pages 2735-2738

  Bienaymé, Hugues ^a   Bouzid, K ^a  

^a SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

TETRAZOLE DERIVATIVE;

ARTICLE; CYCLIZATION; DNA LIBRARY; DRUG SYNTHESIS; NONHUMAN; NUCLEOTIDE SEQUENCE; PEPTIDE SYNTHESIS; PROTEIN SECONDARY STRUCTURE; REACTION ANALYSIS; SOLID PHASE EXTRACTION;

EID: 0032580464     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00283-4     Document Type: Article

References (34)

1. 1. Hermkens, P.H.H. ; Ottenbeijm, H.C.J. ; Rees, D.C. Tetrahedron, 1997, 53, 5643-5678. Balkenhohl, F. ; von den Bussche-Hünnefeld, C. ; Lansky, A. ; Zechel, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337. Thompson, L.A. ; Ellman, J.A. Chem. Rev. 1996, 96, 555-600. Gordon, E.M. ; Barrett, R.W. ; Dower, W.J. ; Fodor, S.P.A. ; Gallop, M.A. J. Med. Chem. 1994, 37, 1233-1251 and 1385-1401.
2. 1. Hermkens, P.H.H. ; Ottenbeijm, H.C.J. ; Rees, D.C. Tetrahedron, 1997, 53, 5643-5678. Balkenhohl, F. ; von den Bussche-Hünnefeld, C. ; Lansky, A. ; Zechel, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337. Thompson, L.A. ; Ellman, J.A. Chem. Rev. 1996, 96, 555-600. Gordon, E.M. ; Barrett, R.W. ; Dower, W.J. ; Fodor, S.P.A. ; Gallop, M.A. J. Med. Chem. 1994, 37, 1233-1251 and 1385-1401.
3. 1. Hermkens, P.H.H. ; Ottenbeijm, H.C.J. ; Rees, D.C. Tetrahedron, 1997, 53, 5643-5678. Balkenhohl, F. ; von den Bussche-Hünnefeld, C. ; Lansky, A. ; Zechel, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337. Thompson, L.A. ; Ellman, J.A. Chem. Rev. 1996, 96, 555-600. Gordon, E.M. ; Barrett, R.W. ; Dower, W.J. ; Fodor, S.P.A. ; Gallop, M.A. J. Med. Chem. 1994, 37, 1233-1251 and 1385-1401.
4. 1. Hermkens, P.H.H. ; Ottenbeijm, H.C.J. ; Rees, D.C. Tetrahedron, 1997, 53, 5643-5678. Balkenhohl, F. ; von den Bussche-Hünnefeld, C. ; Lansky, A. ; Zechel, C. Angew. Chem. Int. Ed. Engl. 1996, 35, 2288-2337. Thompson, L.A. ; Ellman, J.A. Chem. Rev. 1996, 96, 555-600. Gordon, E.M. ; Barrett, R.W. ; Dower, W.J. ; Fodor, S.P.A. ; Gallop, M.A. J. Med. Chem. 1994, 37, 1233-1251 and 1385-1401.
5. 2. Some recent examples of multi-component reactions : Kiselyov, A.S. ; Armstrong, R.W. Tetrahedron Lett. 1997, 38, 6163-6166. Kobayashi, S. ; Akiyama, R. ; Moriwaki, M. Tetrahedron Lett. 1997, 38, 4819-4822. Cavicchioli, M. ; Sixdenier, E. ; Derrey, A. ; Bouyssi, D. ; Balme, G. Tetrahedron Lett. 1997, 38, 1763-1766. Gopalsamy, A. ; Pallai, P.V. Tetrahedron Lett. 1997, 38, 907-910. Petasis, N.A. ; Zavialov, I.A. J. Am. Chem. Soc. 1997, 119, 445-446. Hamper, B.C. ; Dukesherer, D.R. ; South, M.S. Tetrahedron Lett. 1996, 37, 3671-3674. Kobayashi, S. ; Nagayama, S. J. Am. Chem. Soc. 1996, 118, 8977-8978. Armstrong, R.W. ; Combs, A.P. ; Tempest, P.A., Brown, S.D. ; Keating, T.A. Acc. Chem. Res. 1996, 29, 123-131. Lack. O. ; Weber, L. Chimia, 1996, 50, 445-447 Ugi, J. ; Goebel, M. Tetrahedron Lett. 1995, 36, 6043-6046.
6. 2. Some recent examples of multi-component reactions : Kiselyov, A.S. ; Armstrong, R.W. Tetrahedron Lett. 1997, 38, 6163-6166. Kobayashi, S. ; Akiyama, R. ; Moriwaki, M. Tetrahedron Lett. 1997, 38, 4819-4822. Cavicchioli, M. ; Sixdenier, E. ; Derrey, A. ; Bouyssi, D. ; Balme, G. Tetrahedron Lett. 1997, 38, 1763-1766. Gopalsamy, A. ; Pallai, P.V. Tetrahedron Lett. 1997, 38, 907-910. Petasis, N.A. ; Zavialov, I.A. J. Am. Chem. Soc. 1997, 119, 445-446. Hamper, B.C. ; Dukesherer, D.R. ; South, M.S. Tetrahedron Lett. 1996, 37, 3671-3674. Kobayashi, S. ; Nagayama, S. J. Am. Chem. Soc. 1996, 118, 8977-8978. Armstrong, R.W. ; Combs, A.P. ; Tempest, P.A., Brown, S.D. ; Keating, T.A. Acc. Chem. Res. 1996, 29, 123-131. Lack. O. ; Weber, L. Chimia, 1996, 50, 445-447 Ugi, J. ; Goebel, M. Tetrahedron Lett. 1995, 36, 6043-6046.
7. 2. Some recent examples of multi-component reactions : Kiselyov, A.S. ; Armstrong, R.W. Tetrahedron Lett. 1997, 38, 6163-6166. Kobayashi, S. ; Akiyama, R. ; Moriwaki, M. Tetrahedron Lett. 1997, 38, 4819-4822. Cavicchioli, M. ; Sixdenier, E. ; Derrey, A. ; Bouyssi, D. ; Balme, G. Tetrahedron Lett. 1997, 38, 1763-1766. Gopalsamy, A. ; Pallai, P.V. Tetrahedron Lett. 1997, 38, 907-910. Petasis, N.A. ; Zavialov, I.A. J. Am. Chem. Soc. 1997, 119, 445-446. Hamper, B.C. ; Dukesherer, D.R. ; South, M.S. Tetrahedron Lett. 1996, 37, 3671-3674. Kobayashi, S. ; Nagayama, S. J. Am. Chem. Soc. 1996, 118, 8977-8978. Armstrong, R.W. ; Combs, A.P. ; Tempest, P.A., Brown, S.D. ; Keating, T.A. Acc. Chem. Res. 1996, 29, 123-131. Lack. O. ; Weber, L. Chimia, 1996, 50, 445-447 Ugi, J. ; Goebel, M. Tetrahedron Lett. 1995, 36, 6043-6046.
8. 2. Some recent examples of multi-component reactions : Kiselyov, A.S. ; Armstrong, R.W. Tetrahedron Lett. 1997, 38, 6163-6166. Kobayashi, S. ; Akiyama, R. ; Moriwaki, M. Tetrahedron Lett. 1997, 38, 4819-4822. Cavicchioli, M. ; Sixdenier, E. ; Derrey, A. ; Bouyssi, D. ; Balme, G. Tetrahedron Lett. 1997, 38, 1763-1766. Gopalsamy, A. ; Pallai, P.V. Tetrahedron Lett. 1997, 38, 907-910. Petasis, N.A. ; Zavialov, I.A. J. Am. Chem. Soc. 1997, 119, 445-446. Hamper, B.C. ; Dukesherer, D.R. ; South, M.S. Tetrahedron Lett. 1996, 37, 3671-3674. Kobayashi, S. ; Nagayama, S. J. Am. Chem. Soc. 1996, 118, 8977-8978. Armstrong, R.W. ; Combs, A.P. ; Tempest, P.A., Brown, S.D. ; Keating, T.A. Acc. Chem. Res. 1996, 29, 123-131. Lack. O. ; Weber, L. Chimia, 1996, 50, 445-447 Ugi, J. ; Goebel, M. Tetrahedron Lett. 1995, 36, 6043-6046.
9. 2. Some recent examples of multi-component reactions : Kiselyov, A.S. ; Armstrong, R.W. Tetrahedron Lett. 1997, 38, 6163-6166. Kobayashi, S. ; Akiyama, R. ; Moriwaki, M. Tetrahedron Lett. 1997, 38, 4819-4822. Cavicchioli, M. ; Sixdenier, E. ; Derrey, A. ; Bouyssi, D. ; Balme, G. Tetrahedron Lett. 1997, 38, 1763-1766. Gopalsamy, A. ; Pallai, P.V. Tetrahedron Lett. 1997, 38, 907-910. Petasis, N.A. ; Zavialov, I.A. J. Am. Chem. Soc. 1997, 119, 445-446. Hamper, B.C. ; Dukesherer, D.R. ; South, M.S. Tetrahedron Lett. 1996, 37, 3671-3674. Kobayashi, S. ; Nagayama, S. J. Am. Chem. Soc. 1996, 118, 8977-8978. Armstrong, R.W. ; Combs, A.P. ; Tempest, P.A., Brown, S.D. ; Keating, T.A. Acc. Chem. Res. 1996, 29, 123-131. Lack. O. ; Weber, L. Chimia, 1996, 50, 445-447 Ugi, J. ; Goebel, M. Tetrahedron Lett. 1995, 36, 6043-6046.
10. 2. Some recent examples of multi-component reactions : Kiselyov, A.S. ; Armstrong, R.W. Tetrahedron Lett. 1997, 38, 6163-6166. Kobayashi, S. ; Akiyama, R. ; Moriwaki, M. Tetrahedron Lett. 1997, 38, 4819-4822. Cavicchioli, M. ; Sixdenier, E. ; Derrey, A. ; Bouyssi, D. ; Balme, G. Tetrahedron Lett. 1997, 38, 1763-1766. Gopalsamy, A. ; Pallai, P.V. Tetrahedron Lett. 1997, 38, 907-910. Petasis, N.A. ; Zavialov, I.A. J. Am. Chem. Soc. 1997, 119, 445-446. Hamper, B.C. ; Dukesherer, D.R. ; South, M.S. Tetrahedron Lett. 1996, 37, 3671-3674. Kobayashi, S. ; Nagayama, S. J. Am. Chem. Soc. 1996, 118, 8977-8978. Armstrong, R.W. ; Combs, A.P. ; Tempest, P.A., Brown, S.D. ; Keating, T.A. Acc. Chem. Res. 1996, 29, 123-131. Lack. O. ; Weber, L. Chimia, 1996, 50, 445-447 Ugi, J. ; Goebel, M. Tetrahedron Lett. 1995, 36, 6043-6046.
11. 2. Some recent examples of multi-component reactions : Kiselyov, A.S. ; Armstrong, R.W. Tetrahedron Lett. 1997, 38, 6163-6166. Kobayashi, S. ; Akiyama, R. ; Moriwaki, M. Tetrahedron Lett. 1997, 38, 4819-4822. Cavicchioli, M. ; Sixdenier, E. ; Derrey, A. ; Bouyssi, D. ; Balme, G. Tetrahedron Lett. 1997, 38, 1763-1766. Gopalsamy, A. ; Pallai, P.V. Tetrahedron Lett. 1997, 38, 907-910. Petasis, N.A. ; Zavialov, I.A. J. Am. Chem. Soc. 1997, 119, 445-446. Hamper, B.C. ; Dukesherer, D.R. ; South, M.S. Tetrahedron Lett. 1996, 37, 3671-3674. Kobayashi, S. ; Nagayama, S. J. Am. Chem. Soc. 1996, 118, 8977-8978. Armstrong, R.W. ; Combs, A.P. ; Tempest, P.A., Brown, S.D. ; Keating, T.A. Acc. Chem. Res. 1996, 29, 123-131. Lack. O. ; Weber, L. Chimia, 1996, 50, 445-447 Ugi, J. ; Goebel, M. Tetrahedron Lett. 1995, 36, 6043-6046.
12. 2. Some recent examples of multi-component reactions : Kiselyov, A.S. ; Armstrong, R.W. Tetrahedron Lett. 1997, 38, 6163-6166. Kobayashi, S. ; Akiyama, R. ; Moriwaki, M. Tetrahedron Lett. 1997, 38, 4819-4822. Cavicchioli, M. ; Sixdenier, E. ; Derrey, A. ; Bouyssi, D. ; Balme, G. Tetrahedron Lett. 1997, 38, 1763-1766. Gopalsamy, A. ; Pallai, P.V. Tetrahedron Lett. 1997, 38, 907-910. Petasis, N.A. ; Zavialov, I.A. J. Am. Chem. Soc. 1997, 119, 445-446. Hamper, B.C. ; Dukesherer, D.R. ; South, M.S. Tetrahedron Lett. 1996, 37, 3671-3674. Kobayashi, S. ; Nagayama, S. J. Am. Chem. Soc. 1996, 118, 8977-8978. Armstrong, R.W. ; Combs, A.P. ; Tempest, P.A., Brown, S.D. ; Keating, T.A. Acc. Chem. Res. 1996, 29, 123-131. Lack. O. ; Weber, L. Chimia, 1996, 50, 445-447 Ugi, J. ; Goebel, M. Tetrahedron Lett. 1995, 36, 6043-6046.
13. 2. Some recent examples of multi-component reactions : Kiselyov, A.S. ; Armstrong, R.W. Tetrahedron Lett. 1997, 38, 6163-6166. Kobayashi, S. ; Akiyama, R. ; Moriwaki, M. Tetrahedron Lett. 1997, 38, 4819-4822. Cavicchioli, M. ; Sixdenier, E. ; Derrey, A. ; Bouyssi, D. ; Balme, G. Tetrahedron Lett. 1997, 38, 1763-1766. Gopalsamy, A. ; Pallai, P.V. Tetrahedron Lett. 1997, 38, 907-910. Petasis, N.A. ; Zavialov, I.A. J. Am. Chem. Soc. 1997, 119, 445-446. Hamper, B.C. ; Dukesherer, D.R. ; South, M.S. Tetrahedron Lett. 1996, 37, 3671-3674. Kobayashi, S. ; Nagayama, S. J. Am. Chem. Soc. 1996, 118, 8977-8978. Armstrong, R.W. ; Combs, A.P. ; Tempest, P.A., Brown, S.D. ; Keating, T.A. Acc. Chem. Res. 1996, 29, 123-131. Lack. O. ; Weber, L. Chimia, 1996, 50, 445-447 Ugi, J. ; Goebel, M. Tetrahedron Lett. 1995, 36, 6043-6046.
14. 2. Some recent examples of multi-component reactions : Kiselyov, A.S. ; Armstrong, R.W. Tetrahedron Lett. 1997, 38, 6163-6166. Kobayashi, S. ; Akiyama, R. ; Moriwaki, M. Tetrahedron Lett. 1997, 38, 4819-4822. Cavicchioli, M. ; Sixdenier, E. ; Derrey, A. ; Bouyssi, D. ; Balme, G. Tetrahedron Lett. 1997, 38, 1763-1766. Gopalsamy, A. ; Pallai, P.V. Tetrahedron Lett. 1997, 38, 907-910. Petasis, N.A. ; Zavialov, I.A. J. Am. Chem. Soc. 1997, 119, 445-446. Hamper, B.C. ; Dukesherer, D.R. ; South, M.S. Tetrahedron Lett. 1996, 37, 3671-3674. Kobayashi, S. ; Nagayama, S. J. Am. Chem. Soc. 1996, 118, 8977-8978. Armstrong, R.W. ; Combs, A.P. ; Tempest, P.A., Brown, S.D. ; Keating, T.A. Acc. Chem. Res. 1996, 29, 123-131. Lack. O. ; Weber, L. Chimia, 1996, 50, 445-447 Ugi, J. ; Goebel, M. Tetrahedron Lett. 1995, 36, 6043-6046.
15. 3. Ugi reactions have been extensively used both in solution and solid phase : Ugi, I. ; Goebel, M. ; Gruber, B. ; Heilingbrunner, M. ; Heiß, C. ; Hörl, W. ; Kern, O. ; Starnecker, M. Res. Chem. lntermed. 1996, 22, 625-644. Harriman, G.C.B. ; Tetrahedron Lett. 1997, 38, 5591-5594. Rossen, K. ; Sager, J. ; DiMichele, L.M. Tetrahedron Lett. 1997; 38, 3183-3186. Short, K.M. ; Mjalli, A.M.M. Tetrahedron Lett. 1997, 38, 359-352. Sutherlin, D.P. ; Stark, T.M. ; Hughes, R.; Armstrong, R.W. J. Org. Chem. 1996, 61, 8350-8354. Ugi, I. ; Demharter, A. ; Hörl. W. ; Schmid, T. Tetrahedron. 1996, 52, 11657-11664. Demharter, A. ; Hörl, W. ; Eberhardt, H. ; Ugi, I. Angew. Chem. Int. Ed. Engl. 1996, 35, 173-175. Keating, T.A. ; Armstrong, R.W. J. Org. Chem 1996, 61, 8935-8939. Keatiug, T.A. ; Armstrong, R.W. J. Am. Chem. Soc. 1996, 118, 2574-2583. Mjalli. A.M.M. ; Sarshar. S. ; Baiga, T.J. Tetrahedron Lett. 1996, 37, 2943-2946. Strocker, A.M. ; Keating, T.A. ; Tempest, P.A. ; Armstrong, R.W. Tetrahedron Lett. 1996, 37, 1149-1152. Zhang, C. ; Moran, E.J. ; Woiwode, T.F. ; Short, K.M. ; Mjalli, A.M.M. Tetrahedron Lett. .1996, 37, 751-754. Tempest, P.A. ; Brown, S.D. : Armstrong, R.W. Angew. Chem. Int. Ed. Engl. 1996, 35, 640-642.
16. 3. Ugi reactions have been extensively used both in solution and solid phase : Ugi, I. ; Goebel, M. ; Gruber, B. ; Heilingbrunner, M. ; Heiß, C. ; Hörl, W. ; Kern, O. ; Starnecker, M. Res. Chem. lntermed. 1996, 22, 625-644. Harriman, G.C.B. ; Tetrahedron Lett. 1997, 38, 5591-5594. Rossen, K. ; Sager, J. ; DiMichele, L.M. Tetrahedron Lett. 1997; 38, 3183-3186. Short, K.M. ; Mjalli, A.M.M. Tetrahedron Lett. 1997, 38, 359-352. Sutherlin, D.P. ; Stark, T.M. ; Hughes, R.; Armstrong, R.W. J. Org. Chem. 1996, 61, 8350-8354. Ugi, I. ; Demharter, A. ; Hörl. W. ; Schmid, T. Tetrahedron. 1996, 52, 11657-11664. Demharter, A. ; Hörl, W. ; Eberhardt, H. ; Ugi, I. Angew. Chem. Int. Ed. Engl. 1996, 35, 173-175. Keating, T.A. ; Armstrong, R.W. J. Org. Chem 1996, 61, 8935-8939. Keatiug, T.A. ; Armstrong, R.W. J. Am. Chem. Soc. 1996, 118, 2574-2583. Mjalli. A.M.M. ; Sarshar. S. ; Baiga, T.J. Tetrahedron Lett. 1996, 37, 2943-2946. Strocker, A.M. ; Keating, T.A. ; Tempest, P.A. ; Armstrong, R.W. Tetrahedron Lett. 1996, 37, 1149-1152. Zhang, C. ; Moran, E.J. ; Woiwode, T.F. ; Short, K.M. ; Mjalli, A.M.M. Tetrahedron Lett. .1996, 37, 751-754. Tempest, P.A. ; Brown, S.D. : Armstrong, R.W. Angew. Chem. Int. Ed. Engl. 1996, 35, 640-642.
17. 3. Ugi reactions have been extensively used both in solution and solid phase : Ugi, I. ; Goebel, M. ; Gruber, B. ; Heilingbrunner, M. ; Heiß, C. ; Hörl, W. ; Kern, O. ; Starnecker, M. Res. Chem. lntermed. 1996, 22, 625-644. Harriman, G.C.B. ; Tetrahedron Lett. 1997, 38, 5591-5594. Rossen, K. ; Sager, J. ; DiMichele, L.M. Tetrahedron Lett. 1997; 38, 3183-3186. Short, K.M. ; Mjalli, A.M.M. Tetrahedron Lett. 1997, 38, 359-352. Sutherlin, D.P. ; Stark, T.M. ; Hughes, R.; Armstrong, R.W. J. Org. Chem. 1996, 61, 8350-8354. Ugi, I. ; Demharter, A. ; Hörl. W. ; Schmid, T. Tetrahedron. 1996, 52, 11657-11664. Demharter, A. ; Hörl, W. ; Eberhardt, H. ; Ugi, I. Angew. Chem. Int. Ed. Engl. 1996, 35, 173-175. Keating, T.A. ; Armstrong, R.W. J. Org. Chem 1996, 61, 8935-8939. Keatiug, T.A. ; Armstrong, R.W. J. Am. Chem. Soc. 1996, 118, 2574-2583. Mjalli. A.M.M. ; Sarshar. S. ; Baiga, T.J. Tetrahedron Lett. 1996, 37, 2943-2946. Strocker, A.M. ; Keating, T.A. ; Tempest, P.A. ; Armstrong, R.W. Tetrahedron Lett. 1996, 37, 1149-1152. Zhang, C. ; Moran, E.J. ; Woiwode, T.F. ; Short, K.M. ; Mjalli, A.M.M. Tetrahedron Lett. .1996, 37, 751-754. Tempest, P.A. ; Brown, S.D. : Armstrong, R.W. Angew. Chem. Int. Ed. Engl. 1996, 35, 640-642.
18. 3. Ugi reactions have been extensively used both in solution and solid phase : Ugi, I. ; Goebel, M. ; Gruber, B. ; Heilingbrunner, M. ; Heiß, C. ; Hörl, W. ; Kern, O. ; Starnecker, M. Res. Chem. lntermed. 1996, 22, 625-644. Harriman, G.C.B. ; Tetrahedron Lett. 1997, 38, 5591-5594. Rossen, K. ; Sager, J. ; DiMichele, L.M. Tetrahedron Lett. 1997; 38, 3183-3186. Short, K.M. ; Mjalli, A.M.M. Tetrahedron Lett. 1997, 38, 359-352. Sutherlin, D.P. ; Stark, T.M. ; Hughes, R.; Armstrong, R.W. J. Org. Chem. 1996, 61, 8350-8354. Ugi, I. ; Demharter, A. ; Hörl. W. ; Schmid, T. Tetrahedron. 1996, 52, 11657-11664. Demharter, A. ; Hörl, W. ; Eberhardt, H. ; Ugi, I. Angew. Chem. Int. Ed. Engl. 1996, 35, 173-175. Keating, T.A. ; Armstrong, R.W. J. Org. Chem 1996, 61, 8935-8939. Keatiug, T.A. ; Armstrong, R.W. J. Am. Chem. Soc. 1996, 118, 2574-2583. Mjalli. A.M.M. ; Sarshar. S. ; Baiga, T.J. Tetrahedron Lett. 1996, 37, 2943-2946. Strocker, A.M. ; Keating, T.A. ; Tempest, P.A. ; Armstrong, R.W. Tetrahedron Lett. 1996, 37, 1149-1152. Zhang, C. ; Moran, E.J. ; Woiwode, T.F. ; Short, K.M. ; Mjalli, A.M.M. Tetrahedron Lett. .1996, 37, 751-754. Tempest, P.A. ; Brown, S.D. : Armstrong, R.W. Angew. Chem. Int. Ed. Engl. 1996, 35, 640-642.
19. 3. Ugi reactions have been extensively used both in solution and solid phase : Ugi, I. ; Goebel, M. ; Gruber, B. ; Heilingbrunner, M. ; Heiß, C. ; Hörl, W. ; Kern, O. ; Starnecker, M. Res. Chem. lntermed. 1996, 22, 625-644. Harriman, G.C.B. ; Tetrahedron Lett. 1997, 38, 5591-5594. Rossen, K. ; Sager, J. ; DiMichele, L.M. Tetrahedron Lett. 1997; 38, 3183-3186. Short, K.M. ; Mjalli, A.M.M. Tetrahedron Lett. 1997, 38, 359-352. Sutherlin, D.P. ; Stark, T.M. ; Hughes, R.; Armstrong, R.W. J. Org. Chem. 1996, 61, 8350-8354. Ugi, I. ; Demharter, A. ; Hörl. W. ; Schmid, T. Tetrahedron. 1996, 52, 11657-11664. Demharter, A. ; Hörl, W. ; Eberhardt, H. ; Ugi, I. Angew. Chem. Int. Ed. Engl. 1996, 35, 173-175. Keating, T.A. ; Armstrong, R.W. J. Org. Chem 1996, 61, 8935-8939. Keatiug, T.A. ; Armstrong, R.W. J. Am. Chem. Soc. 1996, 118, 2574-2583. Mjalli. A.M.M. ; Sarshar. S. ; Baiga, T.J. Tetrahedron Lett. 1996, 37, 2943-2946. Strocker, A.M. ; Keating, T.A. ; Tempest, P.A. ; Armstrong, R.W. Tetrahedron Lett. 1996, 37, 1149-1152. Zhang, C. ; Moran, E.J. ; Woiwode, T.F. ; Short, K.M. ; Mjalli, A.M.M. Tetrahedron Lett. .1996, 37, 751-754. Tempest, P.A. ; Brown, S.D. : Armstrong, R.W. Angew. Chem. Int. Ed. Engl. 1996, 35, 640-642.
20. 3. Ugi reactions have been extensively used both in solution and solid phase : Ugi, I. ; Goebel, M. ; Gruber, B. ; Heilingbrunner, M. ; Heiß, C. ; Hörl, W. ; Kern, O. ; Starnecker, M. Res. Chem. lntermed. 1996, 22, 625-644. Harriman, G.C.B. ; Tetrahedron Lett. 1997, 38, 5591-5594. Rossen, K. ; Sager, J. ; DiMichele, L.M. Tetrahedron Lett. 1997; 38, 3183-3186. Short, K.M. ; Mjalli, A.M.M. Tetrahedron Lett. 1997, 38, 359-352. Sutherlin, D.P. ; Stark, T.M. ; Hughes, R.; Armstrong, R.W. J. Org. Chem. 1996, 61, 8350-8354. Ugi, I. ; Demharter, A. ; Hörl. W. ; Schmid, T. Tetrahedron. 1996, 52, 11657-11664. Demharter, A. ; Hörl, W. ; Eberhardt, H. ; Ugi, I. Angew. Chem. Int. Ed. Engl. 1996, 35, 173-175. Keating, T.A. ; Armstrong, R.W. J. Org. Chem 1996, 61, 8935-8939. Keatiug, T.A. ; Armstrong, R.W. J. Am. Chem. Soc. 1996, 118, 2574-2583. Mjalli. A.M.M. ; Sarshar. S. ; Baiga, T.J. Tetrahedron Lett. 1996, 37, 2943-2946. Strocker, A.M. ; Keating, T.A. ; Tempest, P.A. ; Armstrong, R.W. Tetrahedron Lett. 1996, 37, 1149-1152. Zhang, C. ; Moran, E.J. ; Woiwode, T.F. ; Short, K.M. ; Mjalli, A.M.M. Tetrahedron Lett. .1996, 37, 751-754. Tempest, P.A. ; Brown, S.D. : Armstrong, R.W. Angew. Chem. Int. Ed. Engl. 1996, 35, 640-642.
21. 3. Ugi reactions have been extensively used both in solution and solid phase : Ugi, I. ; Goebel, M. ; Gruber, B. ; Heilingbrunner, M. ; Heiß, C. ; Hörl, W. ; Kern, O. ; Starnecker, M. Res. Chem. lntermed. 1996, 22, 625-644. Harriman, G.C.B. ; Tetrahedron Lett. 1997, 38, 5591-5594. Rossen, K. ; Sager, J. ; DiMichele, L.M. Tetrahedron Lett. 1997; 38, 3183-3186. Short, K.M. ; Mjalli, A.M.M. Tetrahedron Lett. 1997, 38, 359-352. Sutherlin, D.P. ; Stark, T.M. ; Hughes, R.; Armstrong, R.W. J. Org. Chem. 1996, 61, 8350-8354. Ugi, I. ; Demharter, A. ; Hörl. W. ; Schmid, T. Tetrahedron. 1996, 52, 11657-11664. Demharter, A. ; Hörl, W. ; Eberhardt, H. ; Ugi, I. Angew. Chem. Int. Ed. Engl. 1996, 35, 173-175. Keating, T.A. ; Armstrong, R.W. J. Org. Chem 1996, 61, 8935-8939. Keatiug, T.A. ; Armstrong, R.W. J. Am. Chem. Soc. 1996, 118, 2574-2583. Mjalli. A.M.M. ; Sarshar. S. ; Baiga, T.J. Tetrahedron Lett. 1996, 37, 2943-2946. Strocker, A.M. ; Keating, T.A. ; Tempest, P.A. ; Armstrong, R.W. Tetrahedron Lett. 1996, 37, 1149-1152. Zhang, C. ; Moran, E.J. ; Woiwode, T.F. ; Short, K.M. ; Mjalli, A.M.M. Tetrahedron Lett. .1996, 37, 751-754. Tempest, P.A. ; Brown, S.D. : Armstrong, R.W. Angew. Chem. Int. Ed. Engl. 1996, 35, 640-642.
22. 3. Ugi reactions have been extensively used both in solution and solid phase : Ugi, I. ; Goebel, M. ; Gruber, B. ; Heilingbrunner, M. ; Heiß, C. ; Hörl, W. ; Kern, O. ; Starnecker, M. Res. Chem. lntermed. 1996, 22, 625-644. Harriman, G.C.B. ; Tetrahedron Lett. 1997, 38, 5591-5594. Rossen, K. ; Sager, J. ; DiMichele, L.M. Tetrahedron Lett. 1997; 38, 3183-3186. Short, K.M. ; Mjalli, A.M.M. Tetrahedron Lett. 1997, 38, 359-352. Sutherlin, D.P. ; Stark, T.M. ; Hughes, R.; Armstrong, R.W. J. Org. Chem. 1996, 61, 8350-8354. Ugi, I. ; Demharter, A. ; Hörl. W. ; Schmid, T. Tetrahedron. 1996, 52, 11657-11664. Demharter, A. ; Hörl, W. ; Eberhardt, H. ; Ugi, I. Angew. Chem. Int. Ed. Engl. 1996, 35, 173-175. Keating, T.A. ; Armstrong, R.W. J. Org. Chem 1996, 61, 8935-8939. Keatiug, T.A. ; Armstrong, R.W. J. Am. Chem. Soc. 1996, 118, 2574-2583. Mjalli. A.M.M. ; Sarshar. S. ; Baiga, T.J. Tetrahedron Lett. 1996, 37, 2943-2946. Strocker, A.M. ; Keating, T.A. ; Tempest, P.A. ; Armstrong, R.W. Tetrahedron Lett. 1996, 37, 1149-1152. Zhang, C. ; Moran, E.J. ; Woiwode, T.F. ; Short, K.M. ; Mjalli, A.M.M. Tetrahedron Lett. .1996, 37, 751-754. Tempest, P.A. ; Brown, S.D. : Armstrong, R.W. Angew. Chem. Int. Ed. Engl. 1996, 35, 640-642.
23. 3. Ugi reactions have been extensively used both in solution and solid phase : Ugi, I. ; Goebel, M. ; Gruber, B. ; Heilingbrunner, M. ; Heiß, C. ; Hörl, W. ; Kern, O. ; Starnecker, M. Res. Chem. lntermed. 1996, 22, 625-644. Harriman, G.C.B. ; Tetrahedron Lett. 1997, 38, 5591-5594. Rossen, K. ; Sager, J. ; DiMichele, L.M. Tetrahedron Lett. 1997; 38, 3183-3186. Short, K.M. ; Mjalli, A.M.M. Tetrahedron Lett. 1997, 38, 359-352. Sutherlin, D.P. ; Stark, T.M. ; Hughes, R.; Armstrong, R.W. J. Org. Chem. 1996, 61, 8350-8354. Ugi, I. ; Demharter, A. ; Hörl. W. ; Schmid, T. Tetrahedron. 1996, 52, 11657-11664. Demharter, A. ; Hörl, W. ; Eberhardt, H. ; Ugi, I. Angew. Chem. Int. Ed. Engl. 1996, 35, 173-175. Keating, T.A. ; Armstrong, R.W. J. Org. Chem 1996, 61, 8935-8939. Keatiug, T.A. ; Armstrong, R.W. J. Am. Chem. Soc. 1996, 118, 2574-2583. Mjalli. A.M.M. ; Sarshar. S. ; Baiga, T.J. Tetrahedron Lett. 1996, 37, 2943-2946. Strocker, A.M. ; Keating, T.A. ; Tempest, P.A. ; Armstrong, R.W. Tetrahedron Lett. 1996, 37, 1149-1152. Zhang, C. ; Moran, E.J. ; Woiwode, T.F. ; Short, K.M. ; Mjalli, A.M.M. Tetrahedron Lett. .1996, 37, 751-754. Tempest, P.A. ; Brown, S.D. : Armstrong, R.W. Angew. Chem. Int. Ed. Engl. 1996, 35, 640-642.
24. 3. Ugi reactions have been extensively used both in solution and solid phase : Ugi, I. ; Goebel, M. ; Gruber, B. ; Heilingbrunner, M. ; Heiß, C. ; Hörl, W. ; Kern, O. ; Starnecker, M. Res. Chem. lntermed. 1996, 22, 625-644. Harriman, G.C.B. ; Tetrahedron Lett. 1997, 38, 5591-5594. Rossen, K. ; Sager, J. ; DiMichele, L.M. Tetrahedron Lett. 1997; 38, 3183-3186. Short, K.M. ; Mjalli, A.M.M. Tetrahedron Lett. 1997, 38, 359-352. Sutherlin, D.P. ; Stark, T.M. ; Hughes, R.; Armstrong, R.W. J. Org. Chem. 1996, 61, 8350-8354. Ugi, I. ; Demharter, A. ; Hörl. W. ; Schmid, T. Tetrahedron. 1996, 52, 11657-11664. Demharter, A. ; Hörl, W. ; Eberhardt, H. ; Ugi, I. Angew. Chem. Int. Ed. Engl. 1996, 35, 173-175. Keating, T.A. ; Armstrong, R.W. J. Org. Chem 1996, 61, 8935-8939. Keatiug, T.A. ; Armstrong, R.W. J. Am. Chem. Soc. 1996, 118, 2574-2583. Mjalli. A.M.M. ; Sarshar. S. ; Baiga, T.J. Tetrahedron Lett. 1996, 37, 2943-2946. Strocker, A.M. ; Keating, T.A. ; Tempest, P.A. ; Armstrong, R.W. Tetrahedron Lett. 1996, 37, 1149-1152. Zhang, C. ; Moran, E.J. ; Woiwode, T.F. ; Short, K.M. ; Mjalli, A.M.M. Tetrahedron Lett. .1996, 37, 751-754. Tempest, P.A. ; Brown, S.D. : Armstrong, R.W. Angew. Chem. Int. Ed. Engl. 1996, 35, 640-642.
25. 3. Ugi reactions have been extensively used both in solution and solid phase : Ugi, I. ; Goebel, M. ; Gruber, B. ; Heilingbrunner, M. ; Heiß, C. ; Hörl, W. ; Kern, O. ; Starnecker, M. Res. Chem. lntermed. 1996, 22, 625-644. Harriman, G.C.B. ; Tetrahedron Lett. 1997, 38, 5591-5594. Rossen, K. ; Sager, J. ; DiMichele, L.M. Tetrahedron Lett. 1997; 38, 3183-3186. Short, K.M. ; Mjalli, A.M.M. Tetrahedron Lett. 1997, 38, 359-352. Sutherlin, D.P. ; Stark, T.M. ; Hughes, R.; Armstrong, R.W. J. Org. Chem. 1996, 61, 8350-8354. Ugi, I. ; Demharter, A. ; Hörl. W. ; Schmid, T. Tetrahedron. 1996, 52, 11657-11664. Demharter, A. ; Hörl, W. ; Eberhardt, H. ; Ugi, I. Angew. Chem. Int. Ed. Engl. 1996, 35, 173-175. Keating, T.A. ; Armstrong, R.W. J. Org. Chem 1996, 61, 8935-8939. Keatiug, T.A. ; Armstrong, R.W. J. Am. Chem. Soc. 1996, 118, 2574-2583. Mjalli. A.M.M. ; Sarshar. S. ; Baiga, T.J. Tetrahedron Lett. 1996, 37, 2943-2946. Strocker, A.M. ; Keating, T.A. ; Tempest, P.A. ; Armstrong, R.W. Tetrahedron Lett. 1996, 37, 1149-1152. Zhang, C. ; Moran, E.J. ; Woiwode, T.F. ; Short, K.M. ; Mjalli, A.M.M. Tetrahedron Lett. .1996, 37, 751-754. Tempest, P.A. ; Brown, S.D. : Armstrong, R.W. Angew. Chem. Int. Ed. Engl. 1996, 35, 640-642.
26. 3. Ugi reactions have been extensively used both in solution and solid phase : Ugi, I. ; Goebel, M. ; Gruber, B. ; Heilingbrunner, M. ; Heiß, C. ; Hörl, W. ; Kern, O. ; Starnecker, M. Res. Chem. lntermed. 1996, 22, 625-644. Harriman, G.C.B. ; Tetrahedron Lett. 1997, 38, 5591-5594. Rossen, K. ; Sager, J. ; DiMichele, L.M. Tetrahedron Lett. 1997; 38, 3183-3186. Short, K.M. ; Mjalli, A.M.M. Tetrahedron Lett. 1997, 38, 359-352. Sutherlin, D.P. ; Stark, T.M. ; Hughes, R.; Armstrong, R.W. J. Org. Chem. 1996, 61, 8350-8354. Ugi, I. ; Demharter, A. ; Hörl. W. ; Schmid, T. Tetrahedron. 1996, 52, 11657-11664. Demharter, A. ; Hörl, W. ; Eberhardt, H. ; Ugi, I. Angew. Chem. Int. Ed. Engl. 1996, 35, 173-175. Keating, T.A. ; Armstrong, R.W. J. Org. Chem 1996, 61, 8935-8939. Keatiug, T.A. ; Armstrong, R.W. J. Am. Chem. Soc. 1996, 118, 2574-2583. Mjalli. A.M.M. ; Sarshar. S. ; Baiga, T.J. Tetrahedron Lett. 1996, 37, 2943-2946. Strocker, A.M. ; Keating, T.A. ; Tempest, P.A. ; Armstrong, R.W. Tetrahedron Lett. 1996, 37, 1149-1152. Zhang, C. ; Moran, E.J. ; Woiwode, T.F. ; Short, K.M. ; Mjalli, A.M.M. Tetrahedron Lett. .1996, 37, 751-754. Tempest, P.A. ; Brown, S.D. : Armstrong, R.W. Angew. Chem. Int. Ed. Engl. 1996, 35, 640-642.
27. 3. Ugi reactions have been extensively used both in solution and solid phase : Ugi, I. ; Goebel, M. ; Gruber, B. ; Heilingbrunner, M. ; Heiß, C. ; Hörl, W. ; Kern, O. ; Starnecker, M. Res. Chem. lntermed. 1996, 22, 625-644. Harriman, G.C.B. ; Tetrahedron Lett. 1997, 38, 5591-5594. Rossen, K. ; Sager, J. ; DiMichele, L.M. Tetrahedron Lett. 1997; 38, 3183-3186. Short, K.M. ; Mjalli, A.M.M. Tetrahedron Lett. 1997, 38, 359-352. Sutherlin, D.P. ; Stark, T.M. ; Hughes, R.; Armstrong, R.W. J. Org. Chem. 1996, 61, 8350-8354. Ugi, I. ; Demharter, A. ; Hörl. W. ; Schmid, T. Tetrahedron. 1996, 52, 11657-11664. Demharter, A. ; Hörl, W. ; Eberhardt, H. ; Ugi, I. Angew. Chem. Int. Ed. Engl. 1996, 35, 173-175. Keating, T.A. ; Armstrong, R.W. J. Org. Chem 1996, 61, 8935-8939. Keatiug, T.A. ; Armstrong, R.W. J. Am. Chem. Soc. 1996, 118, 2574-2583. Mjalli. A.M.M. ; Sarshar. S. ; Baiga, T.J. Tetrahedron Lett. 1996, 37, 2943-2946. Strocker, A.M. ; Keating, T.A. ; Tempest, P.A. ; Armstrong, R.W. Tetrahedron Lett. 1996, 37, 1149-1152. Zhang, C. ; Moran, E.J. ; Woiwode, T.F. ; Short, K.M. ; Mjalli, A.M.M. Tetrahedron Lett. .1996, 37, 751-754. Tempest, P.A. ; Brown, S.D. : Armstrong, R.W. Angew. Chem. Int. Ed. Engl. 1996, 35, 640-642.
28. 4. Ugi, I. Angew. Chem. Int. Ed. Engl. 1982, 21, 810-819. Ugi, I. Angew. Chem. Int. Ed. Engl. 1962, 1, 8-. Ugi, I. ; Meyr, R. Chem. Ber. 1961, 2229-2233. Ugi, I. ; Steinbruckner, C. Chem. Ber. 1961, 734-742.
29. 4. Ugi, I. Angew. Chem. Int. Ed. Engl. 1982, 21, 810-819. Ugi, I. Angew. Chem. Int. Ed. Engl. 1962, 1, 8-. Ugi, I. ; Meyr, R. Chem. Ber. 1961, 2229-2233. Ugi, I. ; Steinbruckner, C. Chem. Ber. 1961, 734-742.
30. 4. Ugi, I. Angew. Chem. Int. Ed. Engl. 1982, 21, 810-819. Ugi, I. Angew. Chem. Int. Ed. Engl. 1962, 1, 8-. Ugi, I. ; Meyr, R. Chem. Ber. 1961, 2229-2233. Ugi, I. ; Steinbruckner, C. Chem. Ber. 1961, 734-742.
31. 4. Ugi, I. Angew. Chem. Int. Ed. Engl. 1982, 21, 810-819. Ugi, I. Angew. Chem. Int. Ed. Engl. 1962, 1, 8-. Ugi, I. ; Meyr, R. Chem. Ber. 1961, 2229-2233. Ugi, I. ; Steinbruckner, C. Chem. Ber. 1961, 734-742.
32. 5. Herdeis, C. ; Dimmerling, A. Arch. Pharm. 1986, 319, 473-475. Schöllkopf, U. ; Porsch, P-H. ; Lau, H-H. Liebigs Ann. Chem. 1979, 1444-1446.
33. 5. Herdeis, C. ; Dimmerling, A. Arch. Pharm. 1986, 319, 473-475. Schöllkopf, U. ; Porsch, P-H. ; Lau, H-H. Liebigs Ann. Chem. 1979, 1444-1446.
34. 6. An alcoholic solvent is not only necessary for the in situ desylilation of trimethylsilylazide, but is also advantageous for the four-component reaction.