Solid phase synthesis of 2-acyl-3,7,8-substituted-5-oxo-2- azabicyclo[2.2.2]octane and triaza analogs: Resin activation/capture approach/REACAP technology

Tetrahedron Letters

Volumn 40, Issue 18, 1999, Pages 3491-3494

  Chen, Chixu ^a   Munoz, Benito ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 ACYL 3,7,8 5 OXO 2 AZABICYCLO[2.2.2]OCTANE DERIVATIVE; ALKANE DERIVATIVE; BICYCLO COMPOUND; N ACYL 2 DIHYDRO 4 PYRIDONE DERIVATIVE; TRIAZA DERIVATIVE; TRIAZENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; DIASTEREOISOMER; REACTION ANALYSIS; STEREOCHEMISTRY; STEREOSPECIFICITY; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

EID: 0033617326     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00539-0     Document Type: Article

References (19)

1. 1 For reviews see: a) Kaldor, S.W.; Siegel, M.G. Comb. Chem. Mol. Diversity Drug Disc. 1998, 307-335. b) Kauver, L.M.; Laborde, E. Curr. Opin. Drug Disc. Dev. 1998, 1 (1), 66-70. c) Gordon, E.M.; Patel, D.V.; Jacobs, J.W.; Gordeev, M.F.; Zhou, J. Chimia. 1997, 51 (11), 821-825 d) James, I.W. Mol, Diversity. 1998, 3 (3), 181-190. e) Baxter, A.D. Curr. Opin. Chem. Biol. 1997, 1 (1), 79-85. f) Wilson, S.; Czamik, A..W. Combi. Chem.: Syn. and Appl. 1997, Wiley, New York. g) Kantorowski, E.J.; Kurth, M.J. Mol. Diversity 1997, 2 (4), 207-216.
2. 1 For reviews see: a) Kaldor, S.W.; Siegel, M.G. Comb. Chem. Mol. Diversity Drug Disc. 1998, 307-335. b) Kauver, L.M.; Laborde, E. Curr. Opin. Drug Disc. Dev. 1998, 1 (1), 66-70. c) Gordon, E.M.; Patel, D.V.; Jacobs, J.W.; Gordeev, M.F.; Zhou, J. Chimia. 1997, 51 (11), 821-825 d) James, I.W. Mol, Diversity. 1998, 3 (3), 181-190. e) Baxter, A.D. Curr. Opin. Chem. Biol. 1997, 1 (1), 79-85. f) Wilson, S.; Czamik, A..W. Combi. Chem.: Syn. and Appl. 1997, Wiley, New York. g) Kantorowski, E.J.; Kurth, M.J. Mol. Diversity 1997, 2 (4), 207-216.
3. 1 For reviews see: a) Kaldor, S.W.; Siegel, M.G. Comb. Chem. Mol. Diversity Drug Disc. 1998, 307-335. b) Kauver, L.M.; Laborde, E. Curr. Opin. Drug Disc. Dev. 1998, 1 (1), 66-70. c) Gordon, E.M.; Patel, D.V.; Jacobs, J.W.; Gordeev, M.F.; Zhou, J. Chimia. 1997, 51 (11), 821-825 d) James, I.W. Mol, Diversity. 1998, 3 (3), 181-190. e) Baxter, A.D. Curr. Opin. Chem. Biol. 1997, 1 (1), 79-85. f) Wilson, S.; Czamik, A..W. Combi. Chem.: Syn. and Appl. 1997, Wiley, New York. g) Kantorowski, E.J.; Kurth, M.J. Mol. Diversity 1997, 2 (4), 207-216.
4. 1 For reviews see: a) Kaldor, S.W.; Siegel, M.G. Comb. Chem. Mol. Diversity Drug Disc. 1998, 307-335. b) Kauver, L.M.; Laborde, E. Curr. Opin. Drug Disc. Dev. 1998, 1 (1), 66-70. c) Gordon, E.M.; Patel, D.V.; Jacobs, J.W.; Gordeev, M.F.; Zhou, J. Chimia. 1997, 51 (11), 821-825 d) James, I.W. Mol, Diversity. 1998, 3 (3), 181-190. e) Baxter, A.D. Curr. Opin. Chem. Biol. 1997, 1 (1), 79-85. f) Wilson, S.; Czamik, A..W. Combi. Chem.: Syn. and Appl. 1997, Wiley, New York. g) Kantorowski, E.J.; Kurth, M.J. Mol. Diversity 1997, 2 (4), 207-216.
5. 1 For reviews see: a) Kaldor, S.W.; Siegel, M.G. Comb. Chem. Mol. Diversity Drug Disc. 1998, 307-335. b) Kauver, L.M.; Laborde, E. Curr. Opin. Drug Disc. Dev. 1998, 1 (1), 66-70. c) Gordon, E.M.; Patel, D.V.; Jacobs, J.W.; Gordeev, M.F.; Zhou, J. Chimia. 1997, 51 (11), 821-825 d) James, I.W. Mol, Diversity. 1998, 3 (3), 181-190. e) Baxter, A.D. Curr. Opin. Chem. Biol. 1997, 1 (1), 79-85. f) Wilson, S.; Czamik, A..W. Combi. Chem.: Syn. and Appl. 1997, Wiley, New York. g) Kantorowski, E.J.; Kurth, M.J. Mol. Diversity 1997, 2 (4), 207-216.
6. 1 For reviews see: a) Kaldor, S.W.; Siegel, M.G. Comb. Chem. Mol. Diversity Drug Disc. 1998, 307-335. b) Kauver, L.M.; Laborde, E. Curr. Opin. Drug Disc. Dev. 1998, 1 (1), 66-70. c) Gordon, E.M.; Patel, D.V.; Jacobs, J.W.; Gordeev, M.F.; Zhou, J. Chimia. 1997, 51 (11), 821-825 d) James, I.W. Mol, Diversity. 1998, 3 (3), 181-190. e) Baxter, A.D. Curr. Opin. Chem. Biol. 1997, 1 (1), 79-85. f) Wilson, S.; Czamik, A..W. Combi. Chem.: Syn. and Appl. 1997, Wiley, New York. g) Kantorowski, E.J.; Kurth, M.J. Mol. Diversity 1997, 2 (4), 207-216.
7. 1 For reviews see: a) Kaldor, S.W.; Siegel, M.G. Comb. Chem. Mol. Diversity Drug Disc. 1998, 307-335. b) Kauver, L.M.; Laborde, E. Curr. Opin. Drug Disc. Dev. 1998, 1 (1), 66-70. c) Gordon, E.M.; Patel, D.V.; Jacobs, J.W.; Gordeev, M.F.; Zhou, J. Chimia. 1997, 51 (11), 821-825 d) James, I.W. Mol, Diversity. 1998, 3 (3), 181-190. e) Baxter, A.D. Curr. Opin. Chem. Biol. 1997, 1 (1), 79-85. f) Wilson, S.; Czamik, A..W. Combi. Chem.: Syn. and Appl. 1997, Wiley, New York. g) Kantorowski, E.J.; Kurth, M.J. Mol. Diversity 1997, 2 (4), 207-216.
8. 2. Chen, C.; Munoz, B. Tetrahedron Lett. 1998, 39, 6781-6784.
9. 3. Chen, C.; McDonald, I.A.; Munoz, B. Tetrahedron Lett. 1998, 39, 217-220.
10. 4. Chen, C.; Munoz, B. Tetrahedron Lett. 1998, 39, 3401-3404.
11. 5. For solution acyl-pyridinium examples see a) Comins, D.L.; Joseph, S.P.; Hong, H.; Al-awar, R.S.; Foti, C. J.; Zhang, Y.-M.; Chen, X.; LaMunyon, D.H.; Guarra-Weltzien, M. Pure. Appl. Chem. 1997, 63, 477-481. b) Comins, D.L.; Joseph, S. P.; Goehring, R.R. J. Am. Chem. Soc. 1994, 116, 4719-4728.
12. 5. For solution acyl-pyridinium examples see a) Comins, D.L.; Joseph, S.P.; Hong, H.; Al-awar, R.S.; Foti, C. J.; Zhang, Y.-M.; Chen, X.; LaMunyon, D.H.; Guarra-Weltzien, M. Pure. Appl. Chem. 1997, 63, 477-481. b) Comins, D.L.; Joseph, S. P.; Goehring, R.R. J. Am. Chem. Soc. 1994, 116, 4719-4728.
13. 6. For other solid phase Diels-Alder reactions see a) Wendeborn, S.; Mesmaeker, A.D.; Brill, W. K.-D. Synlett 1998, 865-868. b) Crawshaw, M.; Hird, N.W.; Irie, K.; Nagai, K. Tetrahedron Lett. 1997, 38, 7115-7118. c) Wang, Y.; Wilson, S.R. Tetrahedron Lett. 1997, 38, 4021-4024.
14. 6. For other solid phase Diels-Alder reactions see a) Wendeborn, S.; Mesmaeker, A.D.; Brill, W. K.-D. Synlett 1998, 865-868. b) Crawshaw, M.; Hird, N.W.; Irie, K.; Nagai, K. Tetrahedron Lett. 1997, 38, 7115-7118. c) Wang, Y.; Wilson, S.R. Tetrahedron Lett. 1997, 38, 4021-4024.
15. 6. For other solid phase Diels-Alder reactions see a) Wendeborn, S.; Mesmaeker, A.D.; Brill, W. K.-D. Synlett 1998, 865-868. b) Crawshaw, M.; Hird, N.W.; Irie, K.; Nagai, K. Tetrahedron Lett. 1997, 38, 7115-7118. c) Wang, Y.; Wilson, S.R. Tetrahedron Lett. 1997, 38, 4021-4024.
16. 7. For examples of solution phase Diels-Alder reactions see a) Comins, D.L; Al-awar, R.S. J. Org. Chem. 1992, 57, 4098-4103. b) Polniaszek, R.P.; Dillard, L.W. J. Org. Chem. 1992, 57, 4103-4110.
17. 7. For examples of solution phase Diels-Alder reactions see a) Comins, D.L; Al-awar, R.S. J. Org. Chem. 1992, 57, 4098-4103. b) Polniaszek, R.P.; Dillard, L.W. J. Org. Chem. 1992, 57, 4103-4110.
18. 4Si: C 68.33; H 6.37; N 5.90. Found: C 66.71; H, 6.43; N 5.79.
19. 13C NMR. However, the Diels-Alder reaction was stereospecific.