Solid phase synthesis of benzothiazole and thiophene derivatives based on resin-bound cyclic malonic acid ester

Tetrahedron

Volumn 59, Issue 26, 2003, Pages 4851-4856

  Huang, Xian ^a,b   Tang, Jing ^a  

^a ZHEJIANG UNIVERSITY   (China)

^b INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

Benzothiazole; Cyclic malonic acid ester; Resin bound; Thiophene

Indexed keywords

BENZOTHIAZOLE; BROMINE; CYANIC ACID DERIVATIVE; ESTER; KETONE DERIVATIVE; MALONIC ACID; METHOXIDE SODIUM; OXIDE; PERCHLORIC ACID; RESIN; THIAZOLE DERIVATIVE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID; SYNTHESIS;

EID: 0038515133     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)00688-4     Document Type: Article

References (33)

1. Recent reviews on SPOS, see: (a) Brown R.C.D. J. Chem. Soc., Perkin Trans. 1. 1998;3293-3320 (b) Booth S., Hermkens P.H.H., Ottenheijm H.C.J., Rees D.C. Tetrahedron. 54:1998;15385-15443 (c) James I.W. Tetrahedron. 55:1999;4855-4946 (d) Corbett J.W. Org. Prep. Proced. 30:1998;491-550 (e) Lorsbach B.A., Kurth M. J. Chem. Rev. 99:1999;1549-1581 (f) Guillier F., Orain D., Bradley M. Chem. Rev. 100:2000;2091-2157.
2. Recent reviews on SPOS, see: (a) Brown R.C.D. J. Chem. Soc., Perkin Trans. 1. 1998;3293-3320 (b) Booth S., Hermkens P.H.H., Ottenheijm H.C.J., Rees D.C. Tetrahedron. 54:1998;15385-15443 (c) James I.W. Tetrahedron. 55:1999;4855-4946 (d) Corbett J.W. Org. Prep. Proced. 30:1998;491-550 (e) Lorsbach B.A., Kurth M. J. Chem. Rev. 99:1999;1549-1581 (f) Guillier F., Orain D., Bradley M. Chem. Rev. 100:2000;2091-2157.
3. Recent reviews on SPOS, see: (a) Brown R.C.D. J. Chem. Soc., Perkin Trans. 1. 1998;3293-3320 (b) Booth S., Hermkens P.H.H., Ottenheijm H.C.J., Rees D.C. Tetrahedron. 54:1998;15385-15443 (c) James I.W. Tetrahedron. 55:1999;4855-4946 (d) Corbett J.W. Org. Prep. Proced. 30:1998;491-550 (e) Lorsbach B.A., Kurth M. J. Chem. Rev. 99:1999;1549-1581 (f) Guillier F., Orain D., Bradley M. Chem. Rev. 100:2000;2091-2157.
4. Recent reviews on SPOS, see: (a) Brown R.C.D. J. Chem. Soc., Perkin Trans. 1. 1998;3293-3320 (b) Booth S., Hermkens P.H.H., Ottenheijm H.C.J., Rees D.C. Tetrahedron. 54:1998;15385-15443 (c) James I.W. Tetrahedron. 55:1999;4855-4946 (d) Corbett J.W. Org. Prep. Proced. 30:1998;491-550 (e) Lorsbach B.A., Kurth M. J. Chem. Rev. 99:1999;1549-1581 (f) Guillier F., Orain D., Bradley M. Chem. Rev. 100:2000;2091-2157.
5. Recent reviews on SPOS, see: (a) Brown R.C.D. J. Chem. Soc., Perkin Trans. 1. 1998;3293-3320 (b) Booth S., Hermkens P.H.H., Ottenheijm H.C.J., Rees D.C. Tetrahedron. 54:1998;15385-15443 (c) James I.W. Tetrahedron. 55:1999;4855-4946 (d) Corbett J.W. Org. Prep. Proced. 30:1998;491-550 (e) Lorsbach B.A., Kurth M. J. Chem. Rev. 99:1999;1549-1581 (f) Guillier F., Orain D., Bradley M. Chem. Rev. 100:2000;2091-2157.
6. Recent reviews on SPOS, see: (a) Brown R.C.D. J. Chem. Soc., Perkin Trans. 1. 1998;3293-3320 (b) Booth S., Hermkens P.H.H., Ottenheijm H.C.J., Rees D.C. Tetrahedron. 54:1998;15385-15443 (c) James I.W. Tetrahedron. 55:1999;4855-4946 (d) Corbett J.W. Org. Prep. Proced. 30:1998;491-550 (e) Lorsbach B.A., Kurth M. J. Chem. Rev. 99:1999;1549-1581 (f) Guillier F., Orain D., Bradley M. Chem. Rev. 100:2000;2091-2157.
7. (a) Chen B.C., Huang X., Wang J. Synthesis. 1987;482-483 (b) Chen B.C., Huang X., Ma S.M. Synth. Commun. 17:1987;1519-1522 (c) Ye F.C., Chen B.C., Huang X. Synthesis. 4:1989;317-320 (d) Huang X., Chen B.C., Wu G.Y., Chen H.B. Synth. Commun. 21:1991;1213-1221.
8. (a) Chen B.C., Huang X., Wang J. Synthesis. 1987;482-483 (b) Chen B.C., Huang X., Ma S.M. Synth. Commun. 17:1987;1519-1522 (c) Ye F.C., Chen B.C., Huang X. Synthesis. 4:1989;317-320 (d) Huang X., Chen B.C., Wu G.Y., Chen H.B. Synth. Commun. 21:1991;1213-1221.
9. (a) Chen B.C., Huang X., Wang J. Synthesis. 1987;482-483 (b) Chen B.C., Huang X., Ma S.M. Synth. Commun. 17:1987;1519-1522 (c) Ye F.C., Chen B.C., Huang X. Synthesis. 4:1989;317-320 (d) Huang X., Chen B.C., Wu G.Y., Chen H.B. Synth. Commun. 21:1991;1213-1221.
10. (a) Chen B.C., Huang X., Wang J. Synthesis. 1987;482-483 (b) Chen B.C., Huang X., Ma S.M. Synth. Commun. 17:1987;1519-1522 (c) Ye F.C., Chen B.C., Huang X. Synthesis. 4:1989;317-320 (d) Huang X., Chen B.C., Wu G.Y., Chen H.B. Synth. Commun. 21:1991;1213-1221.
11. (a) Huang X., Liu Z.X. Tetrahedron Lett. 42:2001;7655-7657 (b) Huang X., Liu Z.X. J. Org. Chem. 67:2002;6731-6737.
12. (a) Huang X., Liu Z.X. Tetrahedron Lett. 42:2001;7655-7657 (b) Huang X., Liu Z.X. J. Org. Chem. 67:2002;6731-6737.
13. For reviews on Meldrum's acid, see: (a) McNab H. Chem. Soc. Rev. 7:1978;345-358 (b) Chen B.C. Heterocycles. 32:1991;529-597 (c) Gaberm A.M., McNab H. Synthesis. 2001;2059-2074.
14. For reviews on Meldrum's acid, see: (a) McNab H. Chem. Soc. Rev. 7:1978;345-358 (b) Chen B.C. Heterocycles. 32:1991;529-597 (c) Gaberm A.M., McNab H. Synthesis. 2001;2059-2074.
15. For reviews on Meldrum's acid, see: (a) McNab H. Chem. Soc. Rev. 7:1978;345-358 (b) Chen B.C. Heterocycles. 32:1991;529-597 (c) Gaberm A.M., McNab H. Synthesis. 2001;2059-2074.
16. Augustin M., Guenther E., Wiss Z. Martin-Luther-Univ. Halle-Wittenberg, Math-Naturwiss.Reihe. 38:(3):1989;27-36.
17. (a) Bock M.G., Dipardo R.M., Evans B.E., Rittl K.E., Whittner W.L., Veber D.F., Anderson P.S., Freidiger R.M. J. Med. Chem. 13:1989;16 (b) Kantoci D., Murray E.D., Quiggle D.D., Wechter W.J. J. Med. Chem. 39:1996;1196.
18. (a) Bock M.G., Dipardo R.M., Evans B.E., Rittl K.E., Whittner W.L., Veber D.F., Anderson P.S., Freidiger R.M. J. Med. Chem. 13:1989;16 (b) Kantoci D., Murray E.D., Quiggle D.D., Wechter W.J. J. Med. Chem. 39:1996;1196.
19. (a) Nahed, K. Can. Pat. Appl. CA 2030159/1991 cited in Chem. Abstr. 1991, 115, 198515f. (b) Nahed, K. Can. Pat, EP 430036/1991 cited in Chem. Abstr. 1992, 116, 717c. (c) Geoffrey W., Tracey D.B., Patrizia D., Angela S., Dong F.S., Andrew D.W., Malcolm F.G.S. Bioorg. Med. Chem. Lett. 10:2000;513 (d) Pamler P.J., Trigg R.B., Warrington J.V. J. Med. Chem. 14:1971;248 (e) Chaffma M., Brogden R.N. Drugs. 29:1985;387.
20. (a) Nahed, K. Can. Pat. Appl. CA 2030159/1991 cited in Chem. Abstr. 1991, 115, 198515f. (b) Nahed, K. Can. Pat, EP 430036/1991 cited in Chem. Abstr. 1992, 116, 717c. (c) Geoffrey W., Tracey D.B., Patrizia D., Angela S., Dong F.S., Andrew D.W., Malcolm F.G.S. Bioorg. Med. Chem. Lett. 10:2000;513 (d) Pamler P.J., Trigg R.B., Warrington J.V. J. Med. Chem. 14:1971;248 (e) Chaffma M., Brogden R.N. Drugs. 29:1985;387.
21. (a) Nahed, K. Can. Pat. Appl. CA 2030159/1991 cited in Chem. Abstr. 1991, 115, 198515f. (b) Nahed, K. Can. Pat, EP 430036/1991 cited in Chem. Abstr. 1992, 116, 717c. (c) Geoffrey W., Tracey D.B., Patrizia D., Angela S., Dong F.S., Andrew D.W., Malcolm F.G.S. Bioorg. Med. Chem. Lett. 10:2000;513 (d) Pamler P.J., Trigg R.B., Warrington J.V. J. Med. Chem. 14:1971;248 (e) Chaffma M., Brogden R.N. Drugs. 29:1985;387.
22. (a) Nahed, K. Can. Pat. Appl. CA 2030159/1991 cited in Chem. Abstr. 1991, 115, 198515f. (b) Nahed, K. Can. Pat, EP 430036/1991 cited in Chem. Abstr. 1992, 116, 717c. (c) Geoffrey W., Tracey D.B., Patrizia D., Angela S., Dong F.S., Andrew D.W., Malcolm F.G.S. Bioorg. Med. Chem. Lett. 10:2000;513 (d) Pamler P.J., Trigg R.B., Warrington J.V. J. Med. Chem. 14:1971;248 (e) Chaffma M., Brogden R.N. Drugs. 29:1985;387.
23. (a) Nahed, K. Can. Pat. Appl. CA 2030159/1991 cited in Chem. Abstr. 1991, 115, 198515f. (b) Nahed, K. Can. Pat, EP 430036/1991 cited in Chem. Abstr. 1992, 116, 717c. (c) Geoffrey W., Tracey D.B., Patrizia D., Angela S., Dong F.S., Andrew D.W., Malcolm F.G.S. Bioorg. Med. Chem. Lett. 10:2000;513 (d) Pamler P.J., Trigg R.B., Warrington J.V. J. Med. Chem. 14:1971;248 (e) Chaffma M., Brogden R.N. Drugs. 29:1985;387.
24. (a) Franchetti P., Cappellacci L., Grifantini M., Barzi A., Nocentini G., Yong H.Y., Oconner A., Jayaram H.N., Carrell C., Goldstein B.M. J. Med. Chem. 38:(19):1995;3829 (b) Gromowitz S., Hoernfeldt A.B. Chem. Heterocycl. Comp. 44:1991;1-294.
25. (a) Franchetti P., Cappellacci L., Grifantini M., Barzi A., Nocentini G., Yong H.Y., Oconner A., Jayaram H.N., Carrell C., Goldstein B.M. J. Med. Chem. 38:(19):1995;3829 (b) Gromowitz S., Hoernfeldt A.B. Chem. Heterocycl. Comp. 44:1991;1-294.
26. The loading of resin 4 was determined by reversed titration with hydrochloric acid after saponification with excess NaOH in EtOH.
27. Vittenet H.E.A. Bull. Soc. Chim. Jpn. 21:1899;955.
28. Sidney, S. Quantitative Organic Analysis via Functional Group, 1963, 3rd, 73.
29. Belsteins Handbuch der Organischen Chemie 27, 46.
30. Spitulmik M.J. Synthesis. 1976;730.
31. Chem. Abstr. 52, 9091fg.
32. Belsteins Handbuch der Organischen Chemie 27, 49.
33. Paramasivam R., Ramakrsishnan V.T., Indian. J. Chem. Sect. B. 7:1987;930.