Research ArticleOpen AccessGoogle Scholar indexed
Synthesis, Resolution and Absolute Configuration of 2,3-Dihydro-2-<i>Tert</i>-Butyl-3-<i>N</i>-Benzylquinazolin-4-One: A Possible Chiral Auxiliary for Synthesis of <i>β</i>-Amino Cyclohexancarboxylic Acid
Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Cuernavaca, Mexico
Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Cuernavaca, Mexico
- 1 Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Cuernavaca, Mexico
- 2 Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Cuernavaca, Mexico
International Journal of Organic Chemistry·Volume 04 (2014)·Pages 48–54·Published 28 February 2014·DOI10.4236/ijoc.2014.41007
Copy link · social · email
Abstract
3-Benzyl-2-( tert -butyl)-2,3-dihydroquinazolin-4(1 H )-one rac -11 was resolved via the preparation of diastereomers with N -phthalyl- L -alanine chloride and its absolute configuration was determined by X-ray crystallographic analysis. This heterocycle has potential as a substrate chiral in asymmetric induction due to the steric effects of its tert -butyl group.
KeywordsChiral Auxiliary2-Tert-Butyl-Quinazolin-4-One
- Zhang, Z., Lu, H., Yang, S. and Gao, J. (2010) Synthesis of 2,3-Dihydroquinazolin-4(1H)-Ones by Three-Component Coupling of Isatoic Anhydride, Amines, and Aldehydes Catalyzed by Magnetic Fe3O4 Nanoparticles in Water. Journal of Combinatorial Chemistry, 12, 643-646. http://dx.doi.org/10.1021/cc100047j
- Wu, H., Xie, X. and Liu, G. (2010) Parallel Solution Phase Synthesis of 3,6,7-4(3H)-Quinazolinones and Evaluation of Their Antitumor Activities against Human Cancer. Journal of Combinatorial Chemistry, 12, 346-355. http://dx.doi.org/10.1021/cc900173s
- Bowman, W., Elsegood, M., Stein, T. and Weaver, G. (2007) Radical Reactions with 3H-Quinazolin-4-Ones: Synthesis of Deoxyvasicinone, Mackinazolinone, Luotonin A, Rutaecarpine and Tryptanthrin. Organic & Biomolecular Chemistry, 5, 103-113. http://dx.doi.org/10.1039/b614075k
- Kshirsagar, U., Puranik, V. and Argade, N. (2010) Total Synthesis of Proposed Auranthine. Journal of Organic Chemistry, 75, 2702-2705. http://dx.doi.org/10.1021/jo100400z
- Mhaske, S. and Argade, N. (2006) The Chemistry of Recently Isolated Naturally Occurring Quinazolinone Alkaloids. Tetrahedron, 62, 9787-9826. http://dx.doi.org/10.1016/j.tet.2006.07.098
- Zeng, F. and Alper, H. (2010) One-Step Synthesis of Quinazo-lino[3,2-a]Quinazolinones via Palladium-Catalyzed Domino Addition/Carboxamidation Reactions. Organic Letters, 12, 3642-3644.
- Witt, A. and Bergman, J. (2000) Synthesis and Reactions of Some 2-Vinyl-3H-Quinazolin-4-Ones. Tetrahedron, 56, 7245-7253. http://dx.doi.org/10.1016/S0040-4020(00)00595-0
- Larksarp, C. and Alper, H. (2000) Palladium-Catalyzed Cyclocarbonylation of o-Iodoanilines with Heterocumulenes: Regioselective Preparation of 4(3H)-Quinazolinone Derivatives. Journal of Organic Chemistry, 65, 2773-2777. http://dx.doi.org/10.1021/jo991922r
- Wang, M., Dou, G. and Shi, D. (2010) Efficient and Convenient Synthesis of Pyrrolo[1,2-a]Quinazoline Derivatives with the Aid of Tin(II) Chloride. Journal of Combinatorial Chemistry, 12, 582-586. http://dx.doi.org/10.1021/cc100062e
- Priego, J., Flores, P., Ortiz-Nava, C. and Escalante, J. (2004) Synthesis of Enantiopure Cis- and Trans-2-Aminocyclo- hexane-1-Carboxylic Acids from Octahydroquinazolin-4-Ones. Tetrahedron: Asymmetry, 15, 3545-3549. http://dx.doi.org/10.1016/j.tetasy.2004.08.032
- Cabrera-Rivera, F., Ortiz-Nava, C., Escalante, J., Hernandez-Perez, J. and Ho, M. (2012) Photoinduced Elimination in 2,3-Dihydro-2-Tert-Butyl-3-Benzyl-4(1H)-Quinazolinone: Theoretical Calculations and Radical Trapping Using TEMPO Derivatives. Synlett, 23, 1057-1063. http://dx.doi.org/10.1055/s-0031-1290492