A decarboxylative traceless linker approach for the solid phase synthesis of quinazolines

Tetrahedron Letters

Volumn 40, Issue 5, 1999, Pages 1045-1048

  Cobb, James M ^a   Fiorini, Maria T ^a   Goddard, Chris R ^a   Theoclitou, Maria Elena ^a   Abell, Chris ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

OXALIC ACID; QUINAZOLINE DERIVATIVE; RESIN;

ARTICLE; DECARBOXYLATION; SYNTHESIS;

EID: 0033613705     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)80108-7     Document Type: Article

References (26)

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11. Examples include: Hughes, I. Tetrahedron Lett. 1996, 37, 7595-7598; Gayo, L. M.; Suto, M.J.Tetrahedron Lett. 1997, 38, 211-214; Kroll, F. E. K.; Morphy, R.; Rees, D.; Gani, D. Tetrahedron Lett. 1997, 38, 8573-8576; Plunkett, M. J.; Ellman, J. A. J. Org. Chem. 1995, 60, 6006-6007; Plunkett, M. J.; Ellman, J. A. J. Org. Chem. 1997, 62, 2885-2893; Zhao, X. Y.; Jung, K. W.; Janda, K. D.Tetrahedron Lett. 1997, 38, 977-980; Lorsbach, B. K.; Miller, R. B.; Kurth, M. J. J. Org. Chem. 1996, 61, 8716-8717.
12. Examples include: Hughes, I. Tetrahedron Lett. 1996, 37, 7595-7598; Gayo, L. M.; Suto, M. J.Tetrahedron Lett. 1997, 38, 211-214; Kroll, F. E. K.; Morphy, R.; Rees, D.; Gani, D. Tetrahedron Lett. 1997, 38, 8573-8576; Plunkett, M. J.; Ellman, J. A. J. Org. Chem. 1995, 60, 6006-6007; Plunkett, M. J.; Ellman, J. A. J. Org. Chem. 1997, 62, 2885-2893; Zhao, X. Y.; Jung, K. W.; Janda, K. D.Tetrahedron Lett. 1997, 38, 977-980; Lorsbach, B. K.; Miller, R. B.; Kurth, M. J. J. Org. Chem. 1996, 61, 8716-8717.
13. Examples include: Hughes, I. Tetrahedron Lett. 1996, 37, 7595-7598; Gayo, L. M.; Suto, M.J.Tetrahedron Lett. 1997, 38, 211-214; Kroll, F. E. K.; Morphy, R.; Rees, D.; Gani, D. Tetrahedron Lett. 1997, 38, 8573-8576; Plunkett, M. J.; Ellman, J. A. J. Org. Chem. 1995, 60, 6006-6007; Plunkett, M. J.; Ellman, J. A. J. Org. Chem. 1997, 62, 2885-2893; Zhao, X. Y.; Jung, K. W.; Janda, K. D.Tetrahedron Lett. 1997, 38, 977-980; Lorsbach, B. K.; Miller, R. B.; Kurth, M. J. J. Org. Chem. 1996, 61, 8716-8717.
14. Examples include: Hughes, I. Tetrahedron Lett. 1996, 37, 7595-7598; Gayo, L. M.; Suto, M.J.Tetrahedron Lett. 1997, 38, 211-214; Kroll, F. E. K.; Morphy, R.; Rees, D.; Gani, D. Tetrahedron Lett. 1997, 38, 8573-8576; Plunkett, M. J.; Ellman, J. A. J. Org. Chem. 1995, 60, 6006-6007; Plunkett, M. J.; Ellman, J. A. J. Org. Chem. 1997, 62, 2885-2893; Zhao, X. Y.; Jung, K. W.; Janda, K. D.Tetrahedron Lett. 1997, 38, 977-980; Lorsbach, B. K.; Miller, R. B.; Kurth, M. J. J. Org. Chem. 1996, 61, 8716-8717.
15. Examples include: Hughes, I. Tetrahedron Lett. 1996, 37, 7595-7598; Gayo, L. M.; Suto, M.J.Tetrahedron Lett. 1997, 38, 211-214; Kroll, F. E. K.; Morphy, R.; Rees, D.; Gani, D. Tetrahedron Lett. 1997, 38, 8573-8576; Plunkett, M. J.; Ellman, J. A. J. Org. Chem. 1995, 60, 6006-6007; Plunkett, M. J.; Ellman, J. A. J. Org. Chem. 1997, 62, 2885-2893; Zhao, X. Y.; Jung, K. W.; Janda, K. D.Tetrahedron Lett. 1997, 38, 977-980; Lorsbach, B. K.; Miller, R. B.; Kurth, M. J. J. Org. Chem. 1996, 61, 8716-8717.
16. Examples include: Hughes, I. Tetrahedron Lett. 1996, 37, 7595-7598; Gayo, L. M.; Suto, M.J.Tetrahedron Lett. 1997, 38, 211-214; Kroll, F. E. K.; Morphy, R.; Rees, D.; Gani, D. Tetrahedron Lett. 1997, 38, 8573-8576; Plunkett, M. J.; Ellman, J. A. J. Org. Chem. 1995, 60, 6006-6007; Plunkett, M. J.; Ellman, J. A. J. Org. Chem. 1997, 62, 2885-2893; Zhao, X. Y.; Jung, K. W.; Janda, K. D.Tetrahedron Lett. 1997, 38, 977-980; Lorsbach, B. K.; Miller, R. B.; Kurth, M. J. J. Org. Chem. 1996, 61, 8716-8717.
17. Examples include: Hughes, I. Tetrahedron Lett. 1996, 37, 7595-7598; Gayo, L. M.; Suto, M.J.Tetrahedron Lett. 1997, 38, 211-214; Kroll, F. E. K.; Morphy, R.; Rees, D.; Gani, D. Tetrahedron Lett. 1997, 38, 8573-8576; Plunkett, M. J.; Ellman, J. A. J. Org. Chem. 1995, 60, 6006-6007; Plunkett, M. J.; Ellman, J. A. J. Org. Chem. 1997, 62, 2885-2893; Zhao, X. Y.; Jung, K. W.; Janda, K. D.Tetrahedron Lett. 1997, 38, 977-980; Lorsbach, B. K.; Miller, R. B.; Kurth, M. J. J. Org. Chem. 1996, 61, 8716-8717.
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20. Resin loading was determined by treating the resin with Fmoc-Cl (5.0 equiv.) in dichloromethane in the presence of pyridine (5.0 eq.) for 18 h. The reactive hydroxyl groups were photometrically determined from the amount of Fmoc chromophore released upon treatment of the Fmoc-resin with 20% piperidine in DMF.
21. Preparation of ethyl oxalate linker 1. To hydroxymethylpolystyrene (2.3 g) swelled in dry dichloromethane (30 ml), was added dry triethylamine (290 μl, 1.1 eq.) and catalytic DMAP (0.15 eq.). The mixture was cooled to 0 °C and ethyl oxalyl chloride (1.5 ml) was added dropwise. The reaction was shaken at room temperature overnight and resin was then filtered, washed with dichloromethane (8 × 20 ml), diethyl ether (5 × 20 ml) and dried in vacua. The loading (determined by C and H analysis) was 0.9 mmol / g (100 %)
22. Preparation of resin-bound-quinazolinones 2. To functionalised hydroxypolystyrene resin 1 (1.7 g) swelled in dioxane (5 ml) was added 2-amino-5-chlorobenzamide (1.49 g, 3.5 eq.) and camphor-sulphonic acid (0.6 g, 1 eq.) and the mixture was heated at reflux for 72 h. On cooling, the resin was filtered, washed with DMF (5 x 20 ml), dioxane (5 x 20 ml), dichloromethane (5 x 20 ml) and diethyl ether (5 x 20 ml), and dried in vacuo. The loading (determined by N analysis) 60%.
23. Olah, G. A.; Narang, S. C.; Gupta, B. G. B.; Malhotra, R. J. Org. Chem. 1979, 8, 1247.
24. 2O containing 0.1% TFA), monitored at 254 nm using a UV detector and by a SEDEX Evaporative Light Scattering Detector.
25. Preparation of amino substituted auinazoline 5. To resin 2 (200 mg) swollen in anhydrous DMF (5 ml) was added thionyl chloride (5 ml) and the mixture was heated at reflux for 3 h. The resin was filtered and re-swollen in DMF (5 ml). 3-bromoaniline (150 μl, 5 eq.) in propan-2-ol (5 ml) was added along with conc. HCl (4 drops) and the reaction was shaken at room temperature overnight. The resin was filtered, washed with DMF (5 x 20 ml), dichloromethane (5 x 20 ml), diethyl ether (5 x 20 ml) and dried in vacuo.
26. +).