Microwave-mediated derivatization of poly(styrene-co-allyl alcohol), a key step for the soluble polymer-assisted synthesis of heterocycles

Tetrahedron

Volumn 55, Issue 9, 1999, Pages 2687-2694

  Vanden Eynde, Jean Jacques ^a   Rutot, Delphine ^a  

^a UNIVERSITY OF MONS   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

HETEROCYCLIC COMPOUND; POLY[(STYRENE)CO(ALLYL ALCOHOL)]; POLYMER; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG STRUCTURE; MICROWAVE IRRADIATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 0033605396     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00051-4     Document Type: Article

References (49)

1. (a) Terret, N.K.; Gardner, M.; Gordon, D.W.; Kobylecki, R.J.; Steele, J. Tetrahedron, 1995, 51, 8135-8173. (b) Früchtel, J.S.; Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 17-42. (c) Balkenhol, F.; von dem Bussche-Hünnefeld, C., Lansky, A.; Zechel, C. Angew. Chem. Int. Ed. Engl., 1996, 35, 2288-2337. (d) James, I.W. Molecular Diversity, 1996, 2, 175-180. (e) Hermkens, P.H.H.; Ottenheijm, H.C.J.; Rees, D. Tetrahedron, 1996, 52, 4527-4554. (f) Hermkens, P.H.H.; Ottenheijm, H.C.J.; Rees, D Tetrahedron, 1997, 53, 5643-5678
2. (a) Terret, N.K.; Gardner, M.; Gordon, D.W.; Kobylecki, R.J.; Steele, J. Tetrahedron, 1995, 51, 8135-8173. (b) Früchtel, J.S.; Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 17-42. (c) Balkenhol, F.; von dem Bussche-Hünnefeld, C., Lansky, A.; Zechel, C. Angew. Chem. Int. Ed. Engl., 1996, 35, 2288-2337. (d) James, I.W. Molecular Diversity, 1996, 2, 175-180. (e) Hermkens, P.H.H.; Ottenheijm, H.C.J.; Rees, D. Tetrahedron, 1996, 52, 4527-4554. (f) Hermkens, P.H.H.; Ottenheijm, H.C.J.; Rees, D Tetrahedron, 1997, 53, 5643-5678
3. (a) Terret, N.K.; Gardner, M.; Gordon, D.W.; Kobylecki, R.J.; Steele, J. Tetrahedron, 1995, 51, 8135-8173. (b) Früchtel, J.S.; Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 17-42. (c) Balkenhol, F.; von dem Bussche-Hünnefeld, C., Lansky, A.; Zechel, C. Angew. Chem. Int. Ed. Engl., 1996, 35, 2288-2337. (d) James, I.W. Molecular Diversity, 1996, 2, 175-180. (e) Hermkens, P.H.H.; Ottenheijm, H.C.J.; Rees, D. Tetrahedron, 1996, 52, 4527-4554. (f) Hermkens, P.H.H.; Ottenheijm, H.C.J.; Rees, D Tetrahedron, 1997, 53, 5643-5678
4. (a) Terret, N.K.; Gardner, M.; Gordon, D.W.; Kobylecki, R.J.; Steele, J. Tetrahedron, 1995, 51, 8135-8173. (b) Früchtel, J.S.; Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 17-42. (c) Balkenhol, F.; von dem Bussche-Hünnefeld, C., Lansky, A.; Zechel, C. Angew. Chem. Int. Ed. Engl., 1996, 35, 2288-2337. (d) James, I.W. Molecular Diversity, 1996, 2, 175-180. (e) Hermkens, P.H.H.; Ottenheijm, H.C.J.; Rees, D. Tetrahedron, 1996, 52, 4527-4554. (f) Hermkens, P.H.H.; Ottenheijm, H.C.J.; Rees, D Tetrahedron, 1997, 53, 5643-5678
5. (a) Terret, N.K.; Gardner, M.; Gordon, D.W.; Kobylecki, R.J.; Steele, J. Tetrahedron, 1995, 51, 8135-8173. (b) Früchtel, J.S.; Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 17-42. (c) Balkenhol, F.; von dem Bussche-Hünnefeld, C., Lansky, A.; Zechel, C. Angew. Chem. Int. Ed. Engl., 1996, 35, 2288-2337. (d) James, I.W. Molecular Diversity, 1996, 2, 175-180. (e) Hermkens, P.H.H.; Ottenheijm, H.C.J.; Rees, D. Tetrahedron, 1996, 52, 4527-4554. (f) Hermkens, P.H.H.; Ottenheijm, H.C.J.; Rees, D Tetrahedron, 1997, 53, 5643-5678
6. (a) Terret, N.K.; Gardner, M.; Gordon, D.W.; Kobylecki, R.J.; Steele, J. Tetrahedron, 1995, 51, 8135-8173. (b) Früchtel, J.S.; Jung, G. Angew. Chem. Int. Ed. Engl. 1996, 35, 17-42. (c) Balkenhol, F.; von dem Bussche-Hünnefeld, C., Lansky, A.; Zechel, C. Angew. Chem. Int. Ed. Engl., 1996, 35, 2288-2337. (d) James, I.W. Molecular Diversity, 1996, 2, 175-180. (e) Hermkens, P.H.H.; Ottenheijm, H.C.J.; Rees, D. Tetrahedron, 1996, 52, 4527-4554. (f) Hermkens, P.H.H.; Ottenheijm, H.C.J.; Rees, D Tetrahedron, 1997, 53, 5643-5678
7. (a) Shemyakin, M.M.; Ovchinnikov, Y.A.; Kinyushkin, A.A.; Kozhevnikova, I.V. Tetrahedron Lett., 1965, 27, 2323-2327. (b) Mutter, M; Hagenmaier, H.; Bayer, E. Angew. Chem. Int. Ed. Engl., 1971, 10, 811-812. (c) Bayer, E.; Mutter, M., Nature, 1972, 237, 512-513. (d) Douglas, S.P.; Whithfield, D.M.; Krepinsky, J.J. J. Am. Chem. Soc., 1991, 113, 5095-5097. (e) Ranucci, E.; Spagnoli, G.; Sartore, L.; Ferruti, P. Macromol. Chem. Phys., 1994, 195, 3469-3479. (f) Bonara, G.M. Applied Biochem. Biotech., 1995, 54, 3-17. (g) Douglas, S.P.; Whitfield, D.M.; Krepinsky, J.J. J. Am. Chem. Soc., 1995, 117, 2116-2117. (h) Bonara, G.M.; Baldan, A; Schiavon, O.; Ferruti, P.; Veronese, F.M. Tetrahedron Lett., 1996, 37, 4761-4764. (i) Gravert, D.J.; Janda, K.D. Chem. Rev., 1997, 97, 489-509. (j) Wentworth Jr., P.; Vandersteen, A.M.; Janda, K.D. Chem. Commun., 1997, 759-760.
8. (a) Shemyakin, M.M.; Ovchinnikov, Y.A.; Kinyushkin, A.A.; Kozhevnikova, I.V. Tetrahedron Lett., 1965, 27, 2323-2327. (b) Mutter, M; Hagenmaier, H.; Bayer, E. Angew. Chem. Int. Ed. Engl., 1971, 10, 811-812. (c) Bayer, E.; Mutter, M., Nature, 1972, 237, 512-513. (d) Douglas, S.P.; Whithfield, D.M.; Krepinsky, J.J. J. Am. Chem. Soc., 1991, 113, 5095-5097. (e) Ranucci, E.; Spagnoli, G.; Sartore, L.; Ferruti, P. Macromol. Chem. Phys., 1994, 195, 3469-3479. (f) Bonara, G.M. Applied Biochem. Biotech., 1995, 54, 3-17. (g) Douglas, S.P.; Whitfield, D.M.; Krepinsky, J.J. J. Am. Chem. Soc., 1995, 117, 2116-2117. (h) Bonara, G.M.; Baldan, A; Schiavon, O.; Ferruti, P.; Veronese, F.M. Tetrahedron Lett., 1996, 37, 4761-4764. (i) Gravert, D.J.; Janda, K.D. Chem. Rev., 1997, 97, 489-509. (j) Wentworth Jr., P.; Vandersteen, A.M.; Janda, K.D. Chem. Commun., 1997, 759-760.
9. (a) Shemyakin, M.M.; Ovchinnikov, Y.A.; Kinyushkin, A.A.; Kozhevnikova, I.V. Tetrahedron Lett., 1965, 27, 2323-2327. (b) Mutter, M; Hagenmaier, H.; Bayer, E. Angew. Chem. Int. Ed. Engl., 1971, 10, 811-812. (c) Bayer, E.; Mutter, M., Nature, 1972, 237, 512-513. (d) Douglas, S.P.; Whithfield, D.M.; Krepinsky, J.J. J. Am. Chem. Soc., 1991, 113, 5095-5097. (e) Ranucci, E.; Spagnoli, G.; Sartore, L.; Ferruti, P. Macromol. Chem. Phys., 1994, 195, 3469-3479. (f) Bonara, G.M. Applied Biochem. Biotech., 1995, 54, 3-17. (g) Douglas, S.P.; Whitfield, D.M.; Krepinsky, J.J. J. Am. Chem. Soc., 1995, 117, 2116-2117. (h) Bonara, G.M.; Baldan, A; Schiavon, O.; Ferruti, P.; Veronese, F.M. Tetrahedron Lett., 1996, 37, 4761-4764. (i) Gravert, D.J.; Janda, K.D. Chem. Rev., 1997, 97, 489-509. (j) Wentworth Jr., P.; Vandersteen, A.M.; Janda, K.D. Chem. Commun., 1997, 759-760.
10. (a) Shemyakin, M.M.; Ovchinnikov, Y.A.; Kinyushkin, A.A.; Kozhevnikova, I.V. Tetrahedron Lett., 1965, 27, 2323-2327. (b) Mutter, M; Hagenmaier, H.; Bayer, E. Angew. Chem. Int. Ed. Engl., 1971, 10, 811-812. (c) Bayer, E.; Mutter, M., Nature, 1972, 237, 512-513. (d) Douglas, S.P.; Whithfield, D.M.; Krepinsky, J.J. J. Am. Chem. Soc., 1991, 113, 5095-5097. (e) Ranucci, E.; Spagnoli, G.; Sartore, L.; Ferruti, P. Macromol. Chem. Phys., 1994, 195, 3469-3479. (f) Bonara, G.M. Applied Biochem. Biotech., 1995, 54, 3-17. (g) Douglas, S.P.; Whitfield, D.M.; Krepinsky, J.J. J. Am. Chem. Soc., 1995, 117, 2116-2117. (h) Bonara, G.M.; Baldan, A; Schiavon, O.; Ferruti, P.; Veronese, F.M. Tetrahedron Lett., 1996, 37, 4761-4764. (i) Gravert, D.J.; Janda, K.D. Chem. Rev., 1997, 97, 489-509. (j) Wentworth Jr., P.; Vandersteen, A.M.; Janda, K.D. Chem. Commun., 1997, 759-760.
11. (a) Shemyakin, M.M.; Ovchinnikov, Y.A.; Kinyushkin, A.A.; Kozhevnikova, I.V. Tetrahedron Lett., 1965, 27, 2323-2327. (b) Mutter, M; Hagenmaier, H.; Bayer, E. Angew. Chem. Int. Ed. Engl., 1971, 10, 811-812. (c) Bayer, E.; Mutter, M., Nature, 1972, 237, 512-513. (d) Douglas, S.P.; Whithfield, D.M.; Krepinsky, J.J. J. Am. Chem. Soc., 1991, 113, 5095-5097. (e) Ranucci, E.; Spagnoli, G.; Sartore, L.; Ferruti, P. Macromol. Chem. Phys., 1994, 195, 3469-3479. (f) Bonara, G.M. Applied Biochem. Biotech., 1995, 54, 3-17. (g) Douglas, S.P.; Whitfield, D.M.; Krepinsky, J.J. J. Am. Chem. Soc., 1995, 117, 2116-2117. (h) Bonara, G.M.; Baldan, A; Schiavon, O.; Ferruti, P.; Veronese, F.M. Tetrahedron Lett., 1996, 37, 4761-4764. (i) Gravert, D.J.; Janda, K.D. Chem. Rev., 1997, 97, 489-509. (j) Wentworth Jr., P.; Vandersteen, A.M.; Janda, K.D. Chem. Commun., 1997, 759-760.
12. (a) Shemyakin, M.M.; Ovchinnikov, Y.A.; Kinyushkin, A.A.; Kozhevnikova, I.V. Tetrahedron Lett., 1965, 27, 2323-2327. (b) Mutter, M; Hagenmaier, H.; Bayer, E. Angew. Chem. Int. Ed. Engl., 1971, 10, 811-812. (c) Bayer, E.; Mutter, M., Nature, 1972, 237, 512-513. (d) Douglas, S.P.; Whithfield, D.M.; Krepinsky, J.J. J. Am. Chem. Soc., 1991, 113, 5095-5097. (e) Ranucci, E.; Spagnoli, G.; Sartore, L.; Ferruti, P. Macromol. Chem. Phys., 1994, 195, 3469-3479. (f) Bonara, G.M. Applied Biochem. Biotech., 1995, 54, 3-17. (g) Douglas, S.P.; Whitfield, D.M.; Krepinsky, J.J. J. Am. Chem. Soc., 1995, 117, 2116-2117. (h) Bonara, G.M.; Baldan, A; Schiavon, O.; Ferruti, P.; Veronese, F.M. Tetrahedron Lett., 1996, 37, 4761-4764. (i) Gravert, D.J.; Janda, K.D. Chem. Rev., 1997, 97, 489-509. (j) Wentworth Jr., P.; Vandersteen, A.M.; Janda, K.D. Chem. Commun., 1997, 759-760.
13. (a) Shemyakin, M.M.; Ovchinnikov, Y.A.; Kinyushkin, A.A.; Kozhevnikova, I.V. Tetrahedron Lett., 1965, 27, 2323-2327. (b) Mutter, M; Hagenmaier, H.; Bayer, E. Angew. Chem. Int. Ed. Engl., 1971, 10, 811-812. (c) Bayer, E.; Mutter, M., Nature, 1972, 237, 512-513. (d) Douglas, S.P.; Whithfield, D.M.; Krepinsky, J.J. J. Am. Chem. Soc., 1991, 113, 5095-5097. (e) Ranucci, E.; Spagnoli, G.; Sartore, L.; Ferruti, P. Macromol. Chem. Phys., 1994, 195, 3469-3479. (f) Bonara, G.M. Applied Biochem. Biotech., 1995, 54, 3-17. (g) Douglas, S.P.; Whitfield, D.M.; Krepinsky, J.J. J. Am. Chem. Soc., 1995, 117, 2116-2117. (h) Bonara, G.M.; Baldan, A; Schiavon, O.; Ferruti, P.; Veronese, F.M. Tetrahedron Lett., 1996, 37, 4761-4764. (i) Gravert, D.J.; Janda, K.D. Chem. Rev., 1997, 97, 489-509. (j) Wentworth Jr., P.; Vandersteen, A.M.; Janda, K.D. Chem. Commun., 1997, 759-760.
14. (a) Shemyakin, M.M.; Ovchinnikov, Y.A.; Kinyushkin, A.A.; Kozhevnikova, I.V. Tetrahedron Lett., 1965, 27, 2323-2327. (b) Mutter, M; Hagenmaier, H.; Bayer, E. Angew. Chem. Int. Ed. Engl., 1971, 10, 811-812. (c) Bayer, E.; Mutter, M., Nature, 1972, 237, 512-513. (d) Douglas, S.P.; Whithfield, D.M.; Krepinsky, J.J. J. Am. Chem. Soc., 1991, 113, 5095-5097. (e) Ranucci, E.; Spagnoli, G.; Sartore, L.; Ferruti, P. Macromol. Chem. Phys., 1994, 195, 3469-3479. (f) Bonara, G.M. Applied Biochem. Biotech., 1995, 54, 3-17. (g) Douglas, S.P.; Whitfield, D.M.; Krepinsky, J.J. J. Am. Chem. Soc., 1995, 117, 2116-2117. (h) Bonara, G.M.; Baldan, A; Schiavon, O.; Ferruti, P.; Veronese, F.M. Tetrahedron Lett., 1996, 37, 4761-4764. (i) Gravert, D.J.; Janda, K.D. Chem. Rev., 1997, 97, 489-509. (j) Wentworth Jr., P.; Vandersteen, A.M.; Janda, K.D. Chem. Commun., 1997, 759-760.
15. (a) Shemyakin, M.M.; Ovchinnikov, Y.A.; Kinyushkin, A.A.; Kozhevnikova, I.V. Tetrahedron Lett., 1965, 27, 2323-2327. (b) Mutter, M; Hagenmaier, H.; Bayer, E. Angew. Chem. Int. Ed. Engl., 1971, 10, 811-812. (c) Bayer, E.; Mutter, M., Nature, 1972, 237, 512-513. (d) Douglas, S.P.; Whithfield, D.M.; Krepinsky, J.J. J. Am. Chem. Soc., 1991, 113, 5095-5097. (e) Ranucci, E.; Spagnoli, G.; Sartore, L.; Ferruti, P. Macromol. Chem. Phys., 1994, 195, 3469-3479. (f) Bonara, G.M. Applied Biochem. Biotech., 1995, 54, 3-17. (g) Douglas, S.P.; Whitfield, D.M.; Krepinsky, J.J. J. Am. Chem. Soc., 1995, 117, 2116-2117. (h) Bonara, G.M.; Baldan, A; Schiavon, O.; Ferruti, P.; Veronese, F.M. Tetrahedron Lett., 1996, 37, 4761-4764. (i) Gravert, D.J.; Janda, K.D. Chem. Rev., 1997, 97, 489-509. (j) Wentworth Jr., P.; Vandersteen, A.M.; Janda, K.D. Chem. Commun., 1997, 759-760.
16. (a) Shemyakin, M.M.; Ovchinnikov, Y.A.; Kinyushkin, A.A.; Kozhevnikova, I.V. Tetrahedron Lett., 1965, 27, 2323-2327. (b) Mutter, M; Hagenmaier, H.; Bayer, E. Angew. Chem. Int. Ed. Engl., 1971, 10, 811-812. (c) Bayer, E.; Mutter, M., Nature, 1972, 237, 512-513. (d) Douglas, S.P.; Whithfield, D.M.; Krepinsky, J.J. J. Am. Chem. Soc., 1991, 113, 5095-5097. (e) Ranucci, E.; Spagnoli, G.; Sartore, L.; Ferruti, P. Macromol. Chem. Phys., 1994, 195, 3469-3479. (f) Bonara, G.M. Applied Biochem. Biotech., 1995, 54, 3-17. (g) Douglas, S.P.; Whitfield, D.M.; Krepinsky, J.J. J. Am. Chem. Soc., 1995, 117, 2116-2117. (h) Bonara, G.M.; Baldan, A; Schiavon, O.; Ferruti, P.; Veronese, F.M. Tetrahedron Lett., 1996, 37, 4761-4764. (i) Gravert, D.J.; Janda, K.D. Chem. Rev., 1997, 97, 489-509. (j) Wentworth Jr., P.; Vandersteen, A.M.; Janda, K.D. Chem. Commun., 1997, 759-760.
17. (a) Maquestiau, A., Mayence, A.; Vanden Eynde, J.J. Tetrahedron Lett. 1991, 32, 3839-3840. (b) Vanden Eynde, J.J.; D'Orazio, P.; Mayence, A.; Maquestiau, A. Tetrahedron, 1992, 48, 1263-1268. (c) Vanden Eynde, J.J.; Mayence, A.; Lor, P.; Van Haverbeke, Y. Bull. Soc. Chim. Belg., 1995, 104, 387-392. (d) Vanden Eynde, J.J.; Fromont, D. Bull. Soc. Chim. Belg., 1997, 106, 393-397.
18. (a) Maquestiau, A., Mayence, A.; Vanden Eynde, J.J. Tetrahedron Lett. 1991, 32, 3839-3840. (b) Vanden Eynde, J.J.; D'Orazio, P.; Mayence, A.; Maquestiau, A. Tetrahedron, 1992, 48, 1263-1268. (c) Vanden Eynde, J.J.; Mayence, A.; Lor, P.; Van Haverbeke, Y. Bull. Soc. Chim. Belg., 1995, 104, 387-392. (d) Vanden Eynde, J.J.; Fromont, D. Bull. Soc. Chim. Belg., 1997, 106, 393-397.
19. (a) Maquestiau, A., Mayence, A.; Vanden Eynde, J.J. Tetrahedron Lett. 1991, 32, 3839-3840. (b) Vanden Eynde, J.J.; D'Orazio, P.; Mayence, A.; Maquestiau, A. Tetrahedron, 1992, 48, 1263-1268. (c) Vanden Eynde, J.J.; Mayence, A.; Lor, P.; Van Haverbeke, Y. Bull. Soc. Chim. Belg., 1995, 104, 387-392. (d) Vanden Eynde, J.J.; Fromont, D. Bull. Soc. Chim. Belg., 1997, 106, 393-397.
20. (a) Maquestiau, A., Mayence, A.; Vanden Eynde, J.J. Tetrahedron Lett. 1991, 32, 3839-3840. (b) Vanden Eynde, J.J.; D'Orazio, P.; Mayence, A.; Maquestiau, A. Tetrahedron, 1992, 48, 1263-1268. (c) Vanden Eynde, J.J.; Mayence, A.; Lor, P.; Van Haverbeke, Y. Bull. Soc. Chim. Belg., 1995, 104, 387-392. (d) Vanden Eynde, J.J.; Fromont, D. Bull. Soc. Chim. Belg., 1997, 106, 393-397.
21. Combining "RN = 25119-62-4" and "reactant" gave 17 answers, the most relevant is a European patent, Public. N° 0 449 488 A1, Applic. N° 91302394.1, 1991, Inv. Moren D.M.; Heilman, S.M.; Krepski, L.R.; Rasmussen, J.K.
22. Tietze, L.F.; Steinmetz, A. Synlett, 1996, 667-668.
23. (a) Abramovitch, R.A. Org. Prep. Proced. Int., 1991, 23, 683-711. (b) Berlan, J. Radiat. Phys. Chem., 1995, 45, 581-589. (c) Caddick, S. Tetrahedron, 1995, 51, 10403-10432. (d) Strauss, C.R., Trainor, R.W. Aust. J. Chem., 1995, 48, 1665-1692. (e) Galema, S.A. Chem. Soc. Rev., 1997, 26, 233-238. (f) Shui-Tein, C.; Ping-Hui, T.; Hui-Ming, Y.; Chi-Yue, W.; Kwo-Feng, H.; Shih-Hsiung, W.; Kung-Tsung, W. J. Chin. Chem. Soc., 1997, 44, 169-182.
24. (a) Abramovitch, R.A. Org. Prep. Proced. Int., 1991, 23, 683-711. (b) Berlan, J. Radiat. Phys. Chem., 1995, 45, 581-589. (c) Caddick, S. Tetrahedron, 1995, 51, 10403-10432. (d) Strauss, C.R., Trainor, R.W. Aust. J. Chem., 1995, 48, 1665-1692. (e) Galema, S.A. Chem. Soc. Rev., 1997, 26, 233-238. (f) Shui-Tein, C.; Ping-Hui, T.; Hui-Ming, Y.; Chi-Yue, W.; Kwo-Feng, H.; Shih-Hsiung, W.; Kung-Tsung, W. J. Chin. Chem. Soc., 1997, 44, 169-182.
25. (a) Abramovitch, R.A. Org. Prep. Proced. Int., 1991, 23, 683-711. (b) Berlan, J. Radiat. Phys. Chem., 1995, 45, 581-589. (c) Caddick, S. Tetrahedron, 1995, 51, 10403-10432. (d) Strauss, C.R., Trainor, R.W. Aust. J. Chem., 1995, 48, 1665-1692. (e) Galema, S.A. Chem. Soc. Rev., 1997, 26, 233-238. (f) Shui-Tein, C.; Ping-Hui, T.; Hui-Ming, Y.; Chi-Yue, W.; Kwo-Feng, H.; Shih-Hsiung, W.; Kung-Tsung, W. J. Chin. Chem. Soc., 1997, 44, 169-182.
26. (a) Abramovitch, R.A. Org. Prep. Proced. Int., 1991, 23, 683-711. (b) Berlan, J. Radiat. Phys. Chem., 1995, 45, 581-589. (c) Caddick, S. Tetrahedron, 1995, 51, 10403-10432. (d) Strauss, C.R., Trainor, R.W. Aust. J. Chem., 1995, 48, 1665-1692. (e) Galema, S.A. Chem. Soc. Rev., 1997, 26, 233-238. (f) Shui-Tein, C.; Ping-Hui, T.; Hui-Ming, Y.; Chi-Yue, W.; Kwo-Feng, H.; Shih-Hsiung, W.; Kung-Tsung, W. J. Chin. Chem. Soc., 1997, 44, 169-182.
27. (a) Abramovitch, R.A. Org. Prep. Proced. Int., 1991, 23, 683-711. (b) Berlan, J. Radiat. Phys. Chem., 1995, 45, 581-589. (c) Caddick, S. Tetrahedron, 1995, 51, 10403-10432. (d) Strauss, C.R., Trainor, R.W. Aust. J. Chem., 1995, 48, 1665-1692. (e) Galema, S.A. Chem. Soc. Rev., 1997, 26, 233-238. (f) Shui-Tein, C.; Ping-Hui, T.; Hui-Ming, Y.; Chi-Yue, W.; Kwo-Feng, H.; Shih-Hsiung, W.; Kung-Tsung, W. J. Chin. Chem. Soc., 1997, 44, 169-182.
28. (a) Abramovitch, R.A. Org. Prep. Proced. Int., 1991, 23, 683-711. (b) Berlan, J. Radiat. Phys. Chem., 1995, 45, 581-589. (c) Caddick, S. Tetrahedron, 1995, 51, 10403-10432. (d) Strauss, C.R., Trainor, R.W. Aust. J. Chem., 1995, 48, 1665-1692. (e) Galema, S.A. Chem. Soc. Rev., 1997, 26, 233-238. (f) Shui-Tein, C.; Ping-Hui, T.; Hui-Ming, Y.; Chi-Yue, W.; Kwo-Feng, H.; Shih-Hsiung, W.; Kung-Tsung, W. J. Chin. Chem. Soc., 1997, 44, 169-182.
29. Norcross, B.E.; Clement, G.; Weinstein, M., J. Chem. Educt., 1969, 46, 694-695.
30. Baraldi, P.G.; Simoni, D.; Manfredini, S. Synthesis, 1983, 902-903.
31. Pfister, J.R. Synthesis, 1990, 689-690.
32. Van Haverbeke, Y.; Maquestiau, A.; Vanden Eynde, J.J., J. Heterocycl. Chem., 1979, 16, 773-777.
33. Fitton, A.O.; Smally, R.K. Practical Heterocyclic Chemistry; Academic Press: London. 1968.
34. (a) Lowe, G. Chem. Soc. Rev., 1995, 309-317. (b) Gordon, E.M.; Gallop, M.A.; Patel, D.V. Acc. Chem. Res., 1996, 29, 144-154. (c) Thompson, L.A.; Ellman, J.A. Chem. Rev., 1996, 96, 555-600. (d) Frobel, K.; Krämer, T. Chemie in Unsere Zeit, 1996, 30, 270-285. (e) Warr, W. A. J. Chem. Inf. Comput. Sci., 1997, 37, 134-140. (f) Lam, K.S.; Lebl, M.; Krchnak, R.A. Chem. Rev., 1997, 97, 411-448. (g) Nefzi, A.; Ostresh, J.M.; Houghten, R.A. Chem. Rev., 1997, 97, 49-472. (h) Pirrung, M.C. Chem. Rev., 1997, 97, 473-488.
35. (a) Lowe, G. Chem. Soc. Rev., 1995, 309-317. (b) Gordon, E.M.; Gallop, M.A.; Patel, D.V. Acc. Chem. Res., 1996, 29, 144-154. (c) Thompson, L.A.; Ellman, J.A. Chem. Rev., 1996, 96, 555-600. (d) Frobel, K.; Krämer, T. Chemie in Unsere Zeit, 1996, 30, 270-285. (e) Warr, W. A. J. Chem. Inf. Comput. Sci., 1997, 37, 134-140. (f) Lam, K.S.; Lebl, M.; Krchnak, R.A. Chem. Rev., 1997, 97, 411-448. (g) Nefzi, A.; Ostresh, J.M.; Houghten, R.A. Chem. Rev., 1997, 97, 49-472. (h) Pirrung, M.C. Chem. Rev., 1997, 97, 473-488.
36. (a) Lowe, G. Chem. Soc. Rev., 1995, 309-317. (b) Gordon, E.M.; Gallop, M.A.; Patel, D.V. Acc. Chem. Res., 1996, 29, 144-154. (c) Thompson, L.A.; Ellman, J.A. Chem. Rev., 1996, 96, 555-600. (d) Frobel, K.; Krämer, T. Chemie in Unsere Zeit, 1996, 30, 270-285. (e) Warr, W. A. J. Chem. Inf. Comput. Sci., 1997, 37, 134-140. (f) Lam, K.S.; Lebl, M.; Krchnak, R.A. Chem. Rev., 1997, 97, 411-448. (g) Nefzi, A.; Ostresh, J.M.; Houghten, R.A. Chem. Rev., 1997, 97, 49-472. (h) Pirrung, M.C. Chem. Rev., 1997, 97, 473-488.
37. (a) Lowe, G. Chem. Soc. Rev., 1995, 309-317. (b) Gordon, E.M.; Gallop, M.A.; Patel, D.V. Acc. Chem. Res., 1996, 29, 144-154. (c) Thompson, L.A.; Ellman, J.A. Chem. Rev., 1996, 96, 555-600. (d) Frobel, K.; Krämer, T. Chemie in Unsere Zeit, 1996, 30, 270-285. (e) Warr, W. A. J. Chem. Inf. Comput. Sci., 1997, 37, 134-140. (f) Lam, K.S.; Lebl, M.; Krchnak, R.A. Chem. Rev., 1997, 97, 411-448. (g) Nefzi, A.; Ostresh, J.M.; Houghten, R.A. Chem. Rev., 1997, 97, 49-472. (h) Pirrung, M.C. Chem. Rev., 1997, 97, 473-488.
38. (a) Lowe, G. Chem. Soc. Rev., 1995, 309-317. (b) Gordon, E.M.; Gallop, M.A.; Patel, D.V. Acc. Chem. Res., 1996, 29, 144-154. (c) Thompson, L.A.; Ellman, J.A. Chem. Rev., 1996, 96, 555-600. (d) Frobel, K.; Krämer, T. Chemie in Unsere Zeit, 1996, 30, 270-285. (e) Warr, W. A. J. Chem. Inf. Comput. Sci., 1997, 37, 134-140. (f) Lam, K.S.; Lebl, M.; Krchnak, R.A. Chem. Rev., 1997, 97, 411-448. (g) Nefzi, A.; Ostresh, J.M.; Houghten, R.A. Chem. Rev., 1997, 97, 49-472. (h) Pirrung, M.C. Chem. Rev., 1997, 97, 473-488.
39. (a) Lowe, G. Chem. Soc. Rev., 1995, 309-317. (b) Gordon, E.M.; Gallop, M.A.; Patel, D.V. Acc. Chem. Res., 1996, 29, 144-154. (c) Thompson, L.A.; Ellman, J.A. Chem. Rev., 1996, 96, 555-600. (d) Frobel, K.; Krämer, T. Chemie in Unsere Zeit, 1996, 30, 270-285. (e) Warr, W. A. J. Chem. Inf. Comput. Sci., 1997, 37, 134-140. (f) Lam, K.S.; Lebl, M.; Krchnak, R.A. Chem. Rev., 1997, 97, 411-448. (g) Nefzi, A.; Ostresh, J.M.; Houghten, R.A. Chem. Rev., 1997, 97, 49-472. (h) Pirrung, M.C. Chem. Rev., 1997, 97, 473-488.
40. (a) Lowe, G. Chem. Soc. Rev., 1995, 309-317. (b) Gordon, E.M.; Gallop, M.A.; Patel, D.V. Acc. Chem. Res., 1996, 29, 144-154. (c) Thompson, L.A.; Ellman, J.A. Chem. Rev., 1996, 96, 555-600. (d) Frobel, K.; Krämer, T. Chemie in Unsere Zeit, 1996, 30, 270-285. (e) Warr, W. A. J. Chem. Inf. Comput. Sci., 1997, 37, 134-140. (f) Lam, K.S.; Lebl, M.; Krchnak, R.A. Chem. Rev., 1997, 97, 411-448. (g) Nefzi, A.; Ostresh, J.M.; Houghten, R.A. Chem. Rev., 1997, 97, 49-472. (h) Pirrung, M.C. Chem. Rev., 1997, 97, 473-488.
41. (a) Lowe, G. Chem. Soc. Rev., 1995, 309-317. (b) Gordon, E.M.; Gallop, M.A.; Patel, D.V. Acc. Chem. Res., 1996, 29, 144-154. (c) Thompson, L.A.; Ellman, J.A. Chem. Rev., 1996, 96, 555-600. (d) Frobel, K.; Krämer, T. Chemie in Unsere Zeit, 1996, 30, 270-285. (e) Warr, W. A. J. Chem. Inf. Comput. Sci., 1997, 37, 134-140. (f) Lam, K.S.; Lebl, M.; Krchnak, R.A. Chem. Rev., 1997, 97, 411-448. (g) Nefzi, A.; Ostresh, J.M.; Houghten, R.A. Chem. Rev., 1997, 97, 49-472. (h) Pirrung, M.C. Chem. Rev., 1997, 97, 473-488.
42. Hantzsch, A. Ann., 1882, 215, 1.
43. Schiff, R.; Puliti, J. Chem. Ber., 1883, 16, 1607.
44. Engelman, F. Justus Liebigs Ann. Chem., 1919, 231, 37.
45. Skraup, S. Justus Liebigs Ann. Chem., 1919, 419, 58.
46. Taylor, E.C.; Barton, J.W. J. Am. Chem. Soc., 1959, 81, 2448-2452.
47. Knoevenagel, E. Chem. Ber., 1898, 31, 732.
48. Knoevenagel, E.; Arnot, A. Chem. Ber., 1904, 37, 4497.
49. Knoevenagel, E. Chem. Ber., 1898, 31, 2593.