A new heterocyclic multicomponent reaction for the combinatorial synthesis of fused 3-aminoimidazoles

Angewandte Chemie - International Edition

Volumn 37, Issue 16, 1998, Pages 2234-2237

  Bienaymé, Hugues ^a   Bouzid, Kamel ^a  

^a SANOFI   (France)

Author keywords

Combinatorial chemistry; Cycloadditions; Heterocycles; Multicomponent reactions

Indexed keywords

EID: 0031661388     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19980904)37:16<2234::AID-ANIE2234>3.0.CO;2-R     Document Type: Article

References (34)

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12. Selected examples: a) H. Bienaymé, K. Bouzid, Tetrahedron Lett. 1998, 39, 2735-2738; b) A. S. Kiselyov, R. W. Armstrong, Tetrahedron Lett. 1997, 38, 6163-6166; c) A. Gopalsamy, P. V. Pallai, Tetrahedron Lett. 1997, 38, 907-910; d) S. Sarshar, D. Siev, A. M. M. Mjalli, Tetrahedron Lett. 1996, 37, 835-838; e) O. Lack, L. Weber, Chimia 1996, 50, 445-447; f) P. Wipf, A. Cunnigham, Tetrahedron Lett. 1995, 36, 7819-7822.
13. Selected examples: a) H. Bienaymé, K. Bouzid, Tetrahedron Lett. 1998, 39, 2735-2738; b) A. S. Kiselyov, R. W. Armstrong, Tetrahedron Lett. 1997, 38, 6163-6166; c) A. Gopalsamy, P. V. Pallai, Tetrahedron Lett. 1997, 38, 907-910; d) S. Sarshar, D. Siev, A. M. M. Mjalli, Tetrahedron Lett. 1996, 37, 835-838; e) O. Lack, L. Weber, Chimia 1996, 50, 445-447; f) P. Wipf, A. Cunnigham, Tetrahedron Lett. 1995, 36, 7819-7822.
14. Selected examples: a) H. Bienaymé, K. Bouzid, Tetrahedron Lett. 1998, 39, 2735-2738; b) A. S. Kiselyov, R. W. Armstrong, Tetrahedron Lett. 1997, 38, 6163-6166; c) A. Gopalsamy, P. V. Pallai, Tetrahedron Lett. 1997, 38, 907-910; d) S. Sarshar, D. Siev, A. M. M. Mjalli, Tetrahedron Lett. 1996, 37, 835-838; e) O. Lack, L. Weber, Chimia 1996, 50, 445-447; f) P. Wipf, A. Cunnigham, Tetrahedron Lett. 1995, 36, 7819-7822.
15. Selected examples: a) H. Bienaymé, K. Bouzid, Tetrahedron Lett. 1998, 39, 2735-2738; b) A. S. Kiselyov, R. W. Armstrong, Tetrahedron Lett. 1997, 38, 6163-6166; c) A. Gopalsamy, P. V. Pallai, Tetrahedron Lett. 1997, 38, 907-910; d) S. Sarshar, D. Siev, A. M. M. Mjalli, Tetrahedron Lett. 1996, 37, 835-838; e) O. Lack, L. Weber, Chimia 1996, 50, 445-447; f) P. Wipf, A. Cunnigham, Tetrahedron Lett. 1995, 36, 7819-7822.
16. Selected examples: a) H. Bienaymé, K. Bouzid, Tetrahedron Lett. 1998, 39, 2735-2738; b) A. S. Kiselyov, R. W. Armstrong, Tetrahedron Lett. 1997, 38, 6163-6166; c) A. Gopalsamy, P. V. Pallai, Tetrahedron Lett. 1997, 38, 907-910; d) S. Sarshar, D. Siev, A. M. M. Mjalli, Tetrahedron Lett. 1996, 37, 835-838; e) O. Lack, L. Weber, Chimia 1996, 50, 445-447; f) P. Wipf, A. Cunnigham, Tetrahedron Lett. 1995, 36, 7819-7822.
17. Selected examples: a) H. Bienaymé, K. Bouzid, Tetrahedron Lett. 1998, 39, 2735-2738; b) A. S. Kiselyov, R. W. Armstrong, Tetrahedron Lett. 1997, 38, 6163-6166; c) A. Gopalsamy, P. V. Pallai, Tetrahedron Lett. 1997, 38, 907-910; d) S. Sarshar, D. Siev, A. M. M. Mjalli, Tetrahedron Lett. 1996, 37, 835-838; e) O. Lack, L. Weber, Chimia 1996, 50, 445-447; f) P. Wipf, A. Cunnigham, Tetrahedron Lett. 1995, 36, 7819-7822.
18. With respect to generation of diversity and intense industrial competition, this may become a serious concern.
19. C. G. Newton, Exp. Opin. Ther. Patents 1997, 7, 1183-1194.
20. Other multicomponent reactions can benefit from entropie activation through this bridging strategy. Interestingly, such reactions are also high-yielding and reliable: a) A. Demharter, W. Horl, E. Herdtweck, I. Ugi, Angew Chem. 1996, 108, 185-187; Angew. Chem. Int. Ed. Engl. 1996, 35, 173-175; b) I. Ugi, A. Demharter, W. Hörl, T. Schmid, Tetrahedron 1996, 52, 11657-11664.
21. Other multicomponent reactions can benefit from entropie activation through this bridging strategy. Interestingly, such reactions are also high-yielding and reliable: a) A. Demharter, W. Horl, E. Herdtweck, I. Ugi, Angew Chem. 1996, 108, 185-187; Angew. Chem. Int. Ed. Engl. 1996, 35, 173-175; b) I. Ugi, A. Demharter, W. Hörl, T. Schmid, Tetrahedron 1996, 52, 11657-11664.
22. Other multicomponent reactions can benefit from entropie activation through this bridging strategy. Interestingly, such reactions are also high-yielding and reliable: a) A. Demharter, W. Horl, E. Herdtweck, I. Ugi, Angew Chem. 1996, 108, 185-187; Angew. Chem. Int. Ed. Engl. 1996, 35, 173-175; b) I. Ugi, A. Demharter, W. Hörl, T. Schmid, Tetrahedron 1996, 52, 11657-11664.
23. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-101 255. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: (+44) 1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
24. A similar multicomponent access to 3-aminoimidazo[1,2a]pyridines was recently disclosed: a) C. Blackburn, B. Guan, P. Fleming, K. Shiosaki, S. Tsai, Tetrahedron Lett., in press; for other routes, see b) J.-L. Moutou, M. Schmitt, V. Collot, J.-J. Bourguignon, Tetrahedron Lett. 1996, 37, 1787-1790; c) J. C. Teulade, R. Escale, H. Viols, J. P. Chapat, G. Grassy, A. Carpy, J. M. Léger, J. Chem. Soc. Perkin Trans. I 1983, 2663-2667; d) G. Saint-Ruf, B. Loukalou, C. N'Zouzi, J. Heterocycl. Chem. 1981, 18, 1565-1570; e) N. W. Bristow, P. T. Charlton, D. A. Peak, W. F. Short, J. Chem. Soc. 1954, 616-629.
25. A similar multicomponent access to 3-aminoimidazo[1,2a]pyridines was recently disclosed: a) C. Blackburn, B. Guan, P. Fleming, K. Shiosaki, S. Tsai, Tetrahedron Lett., in press; for other routes, see b) J.-L. Moutou, M. Schmitt, V. Collot, J.-J. Bourguignon, Tetrahedron Lett. 1996, 37, 1787-1790; c) J. C. Teulade, R. Escale, H. Viols, J. P. Chapat, G. Grassy, A. Carpy, J. M. Léger, J. Chem. Soc. Perkin Trans. I 1983, 2663-2667; d) G. Saint-Ruf, B. Loukalou, C. N'Zouzi, J. Heterocycl. Chem. 1981, 18, 1565-1570; e) N. W. Bristow, P. T. Charlton, D. A. Peak, W. F. Short, J. Chem. Soc. 1954, 616-629.
26. A similar multicomponent access to 3-aminoimidazo[1,2a]pyridines was recently disclosed: a) C. Blackburn, B. Guan, P. Fleming, K. Shiosaki, S. Tsai, Tetrahedron Lett., in press; for other routes, see b) J.-L. Moutou, M. Schmitt, V. Collot, J.-J. Bourguignon, Tetrahedron Lett. 1996, 37, 1787-1790; c) J. C. Teulade, R. Escale, H. Viols, J. P. Chapat, G. Grassy, A. Carpy, J. M. Léger, J. Chem. Soc. Perkin Trans. I 1983, 2663-2667; d) G. Saint-Ruf, B. Loukalou, C. N'Zouzi, J. Heterocycl. Chem. 1981, 18, 1565-1570; e) N. W. Bristow, P. T. Charlton, D. A. Peak, W. F. Short, J. Chem. Soc. 1954, 616-629.
27. A similar multicomponent access to 3-aminoimidazo[1,2a]pyridines was recently disclosed: a) C. Blackburn, B. Guan, P. Fleming, K. Shiosaki, S. Tsai, Tetrahedron Lett., in press; for other routes, see b) J.-L. Moutou, M. Schmitt, V. Collot, J.-J. Bourguignon, Tetrahedron Lett. 1996, 37, 1787-1790; c) J. C. Teulade, R. Escale, H. Viols, J. P. Chapat, G. Grassy, A. Carpy, J. M. Léger, J. Chem. Soc. Perkin Trans. I 1983, 2663-2667; d) G. Saint-Ruf, B. Loukalou, C. N'Zouzi, J. Heterocycl. Chem. 1981, 18, 1565-1570; e) N. W. Bristow, P. T. Charlton, D. A. Peak, W. F. Short, J. Chem. Soc. 1954, 616-629.
28. A similar multicomponent access to 3-aminoimidazo[1,2a]pyridines was recently disclosed: a) C. Blackburn, B. Guan, P. Fleming, K. Shiosaki, S. Tsai, Tetrahedron Lett., in press; for other routes, see b) J.-L. Moutou, M. Schmitt, V. Collot, J.-J. Bourguignon, Tetrahedron Lett. 1996, 37, 1787-1790; c) J. C. Teulade, R. Escale, H. Viols, J. P. Chapat, G. Grassy, A. Carpy, J. M. Léger, J. Chem. Soc. Perkin Trans. I 1983, 2663-2667; d) G. Saint-Ruf, B. Loukalou, C. N'Zouzi, J. Heterocycl. Chem. 1981, 18, 1565-1570; e) N. W. Bristow, P. T. Charlton, D. A. Peak, W. F. Short, J. Chem. Soc. 1954, 616-629.
29. [4 + 1] Cycloaddition of isonitriles with various heterodienes is known, though none of the reported examples are of synthetic value in the context of high-throughput synthesis: a) S. Marcaccini, Org. Prep. Proced. Int. 1993, 25, 141-208, and references therein: b) C. Buron, L. El Kaïm, A. Uslu, Tetrahedron Lett. 1997, 38, 8027-8030; c) J. A. Deyrup, M. M. Vestling, W. V. Hagan, H. Y. Yun, Tetrahedron 1969, 25, 1467-1478.
30. [4 + 1] Cycloaddition of isonitriles with various heterodienes is known, though none of the reported examples are of synthetic value in the context of high-throughput synthesis: a) S. Marcaccini, Org. Prep. Proced. Int. 1993, 25, 141-208, and references therein: b) C. Buron, L. El Kaïm, A. Uslu, Tetrahedron Lett. 1997, 38, 8027-8030; c) J. A. Deyrup, M. M. Vestling, W. V. Hagan, H. Y. Yun, Tetrahedron 1969, 25, 1467-1478.
31. [4 + 1] Cycloaddition of isonitriles with various heterodienes is known, though none of the reported examples are of synthetic value in the context of high-throughput synthesis: a) S. Marcaccini, Org. Prep. Proced. Int. 1993, 25, 141-208, and references therein: b) C. Buron, L. El Kaïm, A. Uslu, Tetrahedron Lett. 1997, 38, 8027-8030; c) J. A. Deyrup, M. M. Vestling, W. V. Hagan, H. Y. Yun, Tetrahedron 1969, 25, 1467-1478.
32. a) P.A. Grieco, A. Bahsas, Tetrahedron Lett. 1988, 29, 5855-5858;
33. b) J. M. Mellor, G. Merriman, H. Rataj, G. Reid, Tetrahedron Lett. 1996, 37, 2615-2618, and references therein.
34. Library syntheses and purification will be reported separately.