Solid-phase synthesis of 3-alkyl-2-arylamino-3,4-dihydroquinazolines

Tetrahedron Letters

Volumn 45, Issue 13, 2004, Pages 2727-2730

  Song, Aimin ^a   Mařík, Jan ^a   Lam, Kit S ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Amino 2 nitrobenzenepropanoic acid; 3,4 Dihydroquinazolines; Solid phase synthesis

Indexed keywords

1,3 DIISOPROPYLCARBODIIMIDE; ALDEHYDE DERIVATIVE; AMINO ACID DERIVATIVE; CYANAMIDE; DIAMINE; ISOTHIOCYANIC ACID DERIVATIVE; KETONE DERIVATIVE; QUINAZOLINE DERIVATIVE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; COMBINATORIAL CHEMISTRY; CYCLIZATION; DEPROTECTION REACTION; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; SOLID; SYNTHESIS;

EID: 1542298843     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.02.043     Document Type: Article

References (37)

1. Lam K.S., Salmon S.E., Hersh E.M., Hruby V.J., Kazmierski W.M., Knapp R.J. Nature. 354:1991;82-84.
2. Houghten R.A., Pinilla C., Blondelle S.E., Appel J.R., Dooley C.T., Cuervo J.H. Nature. 354:1991;84-86.
3. Franzén R.G. J. Comb. Chem. 2:2000;195-214.
4. Michael J.P. Nat. Prod. Rep. 19:2002;742-760.
5. Johne S. Sainsbury M. Rodd's Chemistry of Carbon Compounds (2nd ed.). Vol. 4:2000;203-231 Elsevier, Amsterdam.
6. Johne S. Prog. Chem. Org. Nat. Prod. 46:1984;159-229.
7. Witt A., Bergman J. Curr. Org. Chem. 7:2003;659-677.
8. Horton D.A., Bourne G.T., Smythe M.L. Chem. Rev. 103:2003;893-930.
9. Ivachtchenko A.V., Kovalenko S.M., Drushlyak O.G. J. Comb. Chem. 5:2003;775-788.
10. Makino S., Okuzumi T., Tsuji T., Nakanishi E. J. Comb. Chem. 5:2003;756-759.
11. Zhang W., Mayer J.P., Hall S.E., Weigel J.A. J. Comb. Chem. 3:2003;255-256.
12. Sun Q., Zhou X., Kyle D.J. Tetrahedron Lett. 42:2001;4119-4121.
13. Gopalsamy A., Yang H. J. Comb. Chem. 2:2000;378-381.
14. Makino S., Suzuki N., Nakanishi E., Tsuji T. Synlett. 2000;1670-1672.
15. Yang R.-Y., Kaplan A. Tetrahedron Lett. 41:2000;7005-7008.
16. Theoclitou M.-E., Ostresh J.M., Hamashin V., Houghten R.A. Tetrahedron Lett. 41:2000;2051-2054.
17. Wang H., Ganesan A. J. Comb. Chem. 2:2000;186-194.
18. Villalgordo J.M., Obrecht D., Chucholowsky A. Synlett. 1998;1405-1407.
19. Shao H., Colucci M., Tong S., Zhang H., Castelhano A.L. Tetrahedron Lett. 39:1998;7235-7238.
20. Mayer J.P., Lewis G.S., Curtis M.J., Zhang J. Tetrahedron Lett. 38:1997;8445-8448.
21. Gordeev M.F., Hui H.C., Gordon E.M., Patel D.V. Tetrahedron Lett. 38:1997;1729-1732.
22. Smith A.L., Thomson C.G., Leeson P.D. Bioorg. Med. Chem. Lett. 6:1996;1483-1486.
23. Gouilleux L., Fehrentz J.-A., Winternitz F., Martinez J. Tetrahedron Lett. 37:1996;7031-7034.
24. Buckman B.O., Mohan R. Tetrahedron Lett. 37:1996;4439-4442.
25. Wang F., Hauske J.R. Tetrahedron Lett. 38:1997;8651-8654.
26. Zhang J., Barker J., Lou B., Saneii H. Tetrahedron Lett. 42:2001;8405-8408.
27. Srivastava G.K., Kesarwani A.P., Grover R.K., Roy R., Srinivasan T., Kundu B. J. Comb. Chem. 5:2003;769-774.
28. Brown B.B., Wagner D.S., Geysen H.M. Mol. Div. 1:1995;4-12.
29. Wieboldt R., Ramesh D., Jabri E., Karplus P.A., Carpenter B.K., Hess G.P. J. Org. Chem. 67:2002;8827-8831.
30. Szardenings A.K., Burkoth T.S., Look G.C., Campbell D.A. J. Org. Chem. 61:1996;6720-6722.
31. Tumelty D., Schwarz M.K., Cao K., Needels M.C. Tetrahedron Lett. 40:1999;6185-6188.
32. Omar A.-M.M.E., Habib N.S., Aboulwafa O.M. Synthesis. 1977;864-865.
33. You S.W., Lee K.J. Bull. Korean Chem. Soc. 22:2001;1270-1272.
34. Wragg R.T. Tetrahedron Lett. 11:1970;3931-3932.
35. Isobe T., Ishikawa T. J. Org. Chem. 64:1999;6984-6988.
36. 2O solution in DMF (2 mL), and the resulting mixture was shaken for 16 h. The supernatant was removed, and the resin was washed with DMF, DCM, MeOH, and DMF. To the resin was added a solution of 1 M phenyl isothiocyanate and 1 M DIC in DMF (2 mL). The resulting mixture was shaken overnight. The supernatant was removed. The resin was washed with DMF, DCM, MeOH, and DCM, and then dried in vacuo. To the dried resin was added 2 mL of 95% TFA solution in water at ice-bath temperature. The mixture was slowly warmed to room temperature and allowed to mix for 2 h. The supernatant was then collected and the resin was washed with neat TFA (3 × 1 mL). The combined supernatants were concentrated to dryness under a stream of nitrogen, and further dried in vacuo. The crude product was analyzed and purified by HPLC.
37. 6) δ 171.0, 150.4, 139.9, 135.9, 135.5, 132.7, 129.7, 128.2, 128.1, 126.5, 126.4, 126.1, 125.7, 124.4, 122.6, 117.4, 56.3, 49.1, 40.9.