Novel synthesis of oxindole quinazolines using solid phase multiparallel chemistry

Tetrahedron Letters

Volumn 40, Issue 20, 1999, Pages 3881-3884

  Hennequin, Laurent F ^a   Piva Le Blanc, Sylvie ^a  

^a Centre de Recherches   (France)

Author keywords

[No Author keywords available]

Indexed keywords

OXINDOLE QUINAZOLINE; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHEMISTRY; PURIFICATION; SIGNAL TRANSDUCTION; SOLID STATE; SYNTHESIS;

EID: 0033553497     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00638-3     Document Type: Article

References (13)

1. 13C NMR, NOE effects and cross chemistry (unpublished data).
2. 2) Thompson, A.M.; Murray, D.K.; Elliott, W.L.; Fry, D.W.; Nelson, J.A.; Hollis-Showalter, H.D.; Roberts, B.J.; Vincent, P.W.; Denny, W.A. J. Med. Chem. 1997, 40 , 3915-3925
3. 3) Takase, Y.; Saeki, T.; Watanabe, N.; Adachi, H.; Souda, S.; Saito, I. J. Med. Chem. 1994, 37 , 2106-2111
4. 4) See complete issue of Chem Review 1997, 97, issue 2
5. 5) MerriField resin Bachem® D1245 1.24 mmol/g
6. 7 (110°C, 30hrs, Alcohol (4 eq.), NaH (4 eq.), DMF, 84%.
7. 7) Rewcastle, G.W.; Palmer, B.D.; Bridges, A.J.; Showalter, H.D.; Sun L.; Nelson, J.; McMichael, A.; Kraken, A.J.; Fry, D.W., Denny, W.A. J. Med. Chem. 1996, 39 , 918-928
8. 3COOD) δ 1.4 (m, 1H); 1.72 (m, 3H); 1.86 (m, 2H); 3.05 (t, 2H, J = 11.5hz); 3.5 (4H, m); 4.6 (t, 2H, J = 4hz); 6.77 (dd, 1H, J=8.8 and 4 hz); 7.13 (dt, 1H, J = 10.4 and 8.8hz); 7.25(s, 1H); 7.28(d, 1H,J = 9.4hz); 8.01 (t, 1H, J = 9.4hz); 8.72 (s. lH). MS-ESI : 425 [MH]+.
9. 9) Cartridge 1ST Isolute® SCX part N° 9530-0100 particle size 40-70 μM.
10. 10) D.P. Curran, Angew. Chem. Int. Ed. 1998, 37, 1174-1196.
11. 1HNMR (DMSO) δ 4.1 (s, 3H); 4.3 (t, 2H); 2.75 (t, 2H). MS-ESI: 290[MH]+.
12. 12) The conversion of the C-4 supported thioelher quinazoline into the corresponding C4-alkoxy derivatives had been shown to be almost quantitative by reacting a series of alkoxides with the resins (Unpublished data).
13. 13) Sammes, P.; Smith. S.J. Chem. Soc. Perkin Trans I, 1984, 2415-2419