Immobilized aldehydes and olefins in the solid support synthesis of tetrahydroquinolines via a three component condensation

Tetrahedron

Volumn 54, Issue 28, 1998, Pages 7987-7996

  Kiselyov, Alexander S ^a   Smith II, Leon ^a   Virgilio, Alex ^a   Armstrong, Robert W ^a  

^a AMGEN INC   (United States)

Author keywords

Aldehydes; Condensations; Olefins; Solid phase synthesis

Indexed keywords

ALDEHYDE; ALKENE; ANILINE; TETRAHYDROISOQUINOLINE DERIVATIVE; TRIFLUOROACETIC ACID;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; POLYMERIZATION; PRIORITY JOURNAL; SOLID PHASE EXTRACTION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032499988     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00446-3     Document Type: Article

References (41)

1. (1) (a) Armstrong, R.W.; Combs, A.P.; Tempest, P.A.; Brown, S.D.; Keating, T.A. Acc. Chem. Res. 1996,29,123;
2. (b) Armstrong, R.W.; Brown, S.D.; Keating, T.A.; Tempest, P.A. Combinatorial Chemistry, Synthesis and Application, Ed. by S.R. Wilson and A.W. Czarnik, Wiley-Interscience, New York 1997, 153;
3. c) Ugi, I.; Domling, A.; Horl, W. Endeavour 1994, 18, 1152.
4. (2) (a) Tempest, P.A.; Brown, S.D.; Armstrong, R.W. Angew. Chem., Int. Ed. Engl. 1996, 35, 640;
5. (b) Keating, T.A.; Armstrong, R.W. J. Org. Chem. 1996, 61, 8935;
6. (c) Keating, T.A.; Armstrong, R.W. J. Am. Chem. Soc. 1995, 117, 7842;
7. (d) Keating, T.A.; Armstrong, R.W. J. Am. Chem. Soc. 1996, 118, 2574.
8. (3) (a) Grieco, P.; Bahsas, A. Tetrahedron Lett. 1988, 29, 5855;
9. (b) Hayes, T.K.; Kiely, J.S.; Forood, B.; Brady, T.P. Books of Abstracts, 213th ACS National Meeting, Part 2, ACS, San Francisco, 1997, 275;
10. (c) Campos, P.J.; Lamaza, I.; Rodriguez, M.A.; Canal, G. Tetrahedron Lett. 1997, 38, 6741.
11. (4) (a) Clerici, A.; Porta, O. Tetrahedron Lett. 1990, 31, 2069;
12. (b) Mellor, J.M.; Merriman, G.D.; Riviere, P. Tetrahedron Lett. 1991, 32, 6115;
13. (c) Mellor, J.M.; Merriman, G.D. Tetrahedron 1995, 51, 6115;
14. (d) Cabral, J.; Laszlo, P. Tetrahedron Lett. 1989, 30, 7237;
15. (e) Povarov, L.S. Russ. Chem. Rev. 1967, 36, 656;
16. f) Lucchini, V.; Prato, M.; Scorrano, G.; Tecilla, P. J. Org. Chem. 1988, 53, 2251;
17. g) Nomura, Y.; Kimura, M.; Takeuchi, S.; Tomoda, S. Chem. Lett. 1978, 267;
18. h) Cheng, Y.S.; Ho, E.; Mariano, P.S.; Ammon, H.L. J. Org. Chem. 1985, 56, 5678;
19. i) Job, T.; Hagihara, N. Tetrahedron Lett. 1967, 4199;
20. j) Annunziata, R.; Cinquini, M.; Cozzi, F.; Molteni, V.; Schupp, O. Tetrahedron 1997, 53, 9715.
21. (5) (a) Kobayashi, S.; Nagayama, S. J. Org. Chem. 1996, 61, 2256;
22. (b) Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1996, 118, 8977;
23. c) Kobayashi, S.; Ishitani, H.; Nagayama, S. Synthesis 1995, 1095;
24. d) Kobayashi, S.; Araki, M.; Ishitani, H.; Nagayama, S.; Hachiya, I. SynLett 1995, 233;
25. e) Kobayashi, S.; Ishitani, H.; Nagayama, S. Chem. Lett. 1995, 423.
26. (6) For synthesis of tetrahydroquinolines and their biological activity see for example: (a) Katritzky, A.R.; Rachwal, S.; Rachwal, B. Tetrahedron 1996, 52, 15031;
27. (b) Kokwaro, G.O.; Taylor, G. Drug Chem. Toxicol. 1990, 13, 347;
28. c) Prankerd, R.J.; Ahmed, S.M. J. Pharm. Pharmacol. 1992, 44, 259;
29. (d) Prankerd, R.J.; Ahmed, S.M. J. Pharm. Pharmacol. 1992, 44, 261;
30. (e) Kimura, T.; Imanishi, S.; Arita, M. J. Cardivasc. Pharmacol. 1989, 13, 767;
31. (f) Rekka, E.; Mannhold, R.M.; Bast, A.; Timmerman, H. Biochem. Pharmacol. 1990, 39, 95;
32. (g) Leeson, P.D.; Carling, R.W.; Moore, K.W., Moseley, A.M.; Smith, J.D.; Stevenson, G.; Chan, T.; Baker, R.; Foster, A.C.; Grimwood, S.; Kemp, J.A.; Marshall, G.R.; Hoogsteen, K. J. Med. Chem. 1992, 35, 1954;
33. (h) Pangalos, M.N.; Francis, P.T.; Foster, A.C.; Pearson, R.C.A.; Middlemiss, D.N.; Bowen, D.M. Brain Res. 1992, 596, 223;
34. (i) Yoneda, Y.; Suzuki, T.; Ogita, K.; Han, D. J. Neurochem. 1993, 60, 634;
35. j) Sarges, R.; Gallagher, A.; Chambers, T.J.; Yen, L.-A. J. Med. Chem. 1993, 36, 2828;
36. k) Anzini, M.; Capelli, A.; Vomero, S.; Giorgi, G.; Langer, T.; Hamon, M.; Merahi, N.; Emerit, B.M.; Cagnotto, A.; Skorupska, M.; Mennini, T.; Pinto, J.C. J. Med. Chem. 1995, 38, 2692.
37. (7) Kiselyov, A.S.; Armstrong, R.W. Tetrahedron Lett. 1997, 38, 6163.
38. (8) Prepared according to Fivush, A.M.; Willson, T.M. Tetrahedron Lett. 1997, 38, 7151.
39. 1H NMR, ESIMS, and HPLC.
40. (10) Hird, N.W.; Irie, K.; Nagai, K. Tetrahedron Lett. 1997, 38, 7111; similar to the observations described in this paper, we found that efficient preparation of the target olefin resin 3 or 4 required rigorously dried aldehyde resin.
41. (11) The nonreacted Schiff base, the common impurity in the synthesis of tetrahydroquinolines using resinbound aniline, was not detected.