Synthesis, Resolution and Absolute Configuration of 2,3-Dihydro-2-Tert-Butyl-3-N-Benzylquinazolin-4-One: A Possible Chiral Auxiliary for Synthesis of β-Amino Cyclohexancarboxylic Acid
3-Benzyl-2-(tert-butyl)-2,3-dihydroquinazolin-4(1H)-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.
References
[1]
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
[2]
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
[3]
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
[4]
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
[5]
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
[6]
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.
[7]
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
[8]
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
[9]
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
[10]
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
[11]
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
[12]
Escalante, J., Flores, P. and Priego, J. (2004) Synthesis of 2,3-Dihydro-4(1H)-Quinazolinones. Heterocycles, 63, 2019-2032. http://dx.doi.org/10.3987/COM-04-10130
[13]
Escalante, J., Ortiz-Nava, C., Flores, P., Priego, J. and Garcia-Martinez, C. (2007) Synthesis, NMR and Crystallographic Studies of 2-Substituted Dihydroquinazolinones Derived from (S)-Phenylethylamine. Molecules, 12, 173-182. http://dx.doi.org/10.3390/12020173
[14]
Escalante, J. and Gonzalez-Tototzin, M. (2003) Synthesis, Resolution and Absolute Configuration of Trans-4,5-Diphenyl-Pyrrolidin-2-One: A Possible Chiral Auxiliary. Tetrahedron: Asymmetry, 14, 981-985. http://dx.doi.org/10.1016/S0957-4166(03)00097-1
[15]
Seebach, D., Lamatsch, B., Amstutz, R., Beck, A., Dobler, M., Egli, M., Fitzi, R., Gautschi, M., Herradon, B., et al. (1992) Structure and Reactivity of Five- and Six-Ring N,N-, N,O-, and O,O-Acetals: A Lesson in Allylic 1,3-Strain (A1,3 Strain). Helvetica Chimica Acta, 75, 913-934. http://dx.doi.org/10.1002/hlca.19920750326
[16]
Murer, P., Rheiner, B., Juaristi, E. and Seebach, D. (1994) Enantioselective Synthesis of β-Amino Acids. 5. Stereoselective Reaction of Chiral Pyrimidinone Enolates with Aldehydes. Heterocycles, 39, 319-344. http://dx.doi.org/10.3987/COM-94-S(B)35
[17]
Seebach, D., Boog, A. and Schweizer, W.B. (1999) EPC-Synthesis of B-Amino Acid Derivatives through Lithiades Hydropyrimidines. European Journal of Organic Chemistry, 1999, 335-360.
[18]
Ramirez-Quiros, Y., Balderas, M., Escalante, J., Quintana, D., Gallardo, It., Madrigal, D., Molins, E. and Juaristi, E. (1999) X-Ray Crystallographic Study of Substituted Perhydropyrimidinones. Extreme Changes in Ring Conformation. Journal of Organic Chemistry, 64, 8668-8680. http://dx.doi.org/10.1021/jo991297q
[19]
Johnson, F. (1968) Allylic Strain in Six-Membered Rings. Chemical Reviews, 68, 375-413. http://dx.doi.org/10.1021/cr60254a001
[20]
Hoffmann, R. (1989) Allylic 1,3-Strain as a Controlling Factor in Stereoselective Transformations. Chemical Reviews, 89, 1841-1860. http://dx.doi.org/10.1021/cr00098a009
[21]
Broeker, J., Hoffmann, R. and Houk, K. N. (1991) Conformational Analysis of Chiral Alkenes and Oxonium Ions: Ab Initio Molecular Orbital Calculations and an Improved MM2 Force Field. Journal of the American Chemical Society, 113, 5006-5017. http://dx.doi.org/10.1021/ja00013a041
[22]
Still, W., Kahn, M. and Mitra, A. (1978) Rapid Chromatographic Technique for Preparative Separations with Moderate Resolution. Journal of Organic Chemistry, 43, 2923-2925. http://dx.doi.org/10.1021/jo00408a041
[23]
Sheldrick, G.M. (1998) SHELX97, Programs for Crystal Structure Analysis, Release 97-2. Institute for Inorganic Chemistry der Universität, Göttingen.
[24]
Camps, P., Perez, F., Soldevilla, N. and Borrego, M. (1999) (R)- and (S)-3-Hydroxy-4,4-Dimethyl-1-Phenyl-2-Pyrrolidinone as Chiral Auxiliaries in the Enantioselective Preparation of α-Amino Acids. Tetrahedron: Asymmetry, 10, 493-509. http://dx.doi.org/10.1016/S0957-4166(99)00018-X
[25]
Crystallographic Data Is Deposited at Cambridge Crystallographic Data Center (CCDC: No. 900252).