IJOC  Vol.4 No.1 , March 2014
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
ABSTRACT
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.

Cite this paper
Cabrera-Rivera, F. and Escalante, J. (2014) 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. International Journal of Organic Chemistry, 4, 48-54. doi: 10.4236/ijoc.2014.41007.
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).

 
 
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