Catalytic carbonylation of 3-bromomethyl-5,6-dihydro-4H-1,2-oxazines: General approach to the synthesis of 3-methoxycarbonylmethyl-5,6-dihydro-4H-1,2- oxazines from available precursors

Synlett

Volumn , Issue 14, 2006, Pages 2239-2240

  Eliseev, Oleg L ^a   Ivashkin, Pavel E ^a   Ostapenko, Aduard G ^a   Lesiv, Alexey V ^a   Khomutova, Yulia A ^a   Ioffe, Sema L ^a   Lapidus, Albert L ^a  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

1,2 oxazines; Carbonylations; Palladium

Indexed keywords

3 BROMOMETHYL 5,6 DIHYDRO 4H 1,2 OXAZINE DERIVATIVE; 3 METHOXYCARBONYLMETHYL 5,6 DIHYDRO 4H 1,2 OXAZINE DERIVATIVE; 5,6 DIHYDRO 4H 1,2 OXAZINE 3 YL ACETATE DERIVATIVE; CARBON MONOXIDE; FUNCTIONAL GROUP; METHYL [4 (4 METHOXYPHENYL) 6,6 DIMETHYL 5,6 DIHYDRO 4H 1,2 OXAZIN 3 YL]ACETATE; OXAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBONYLATION; CATALYSIS; CHEMICAL STRUCTURE; COLUMN CHROMATOGRAPHY; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRECURSOR; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 33748687578     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-949616     Document Type: Article

References (10)

1. Klenov, M. S.; Lesiv, A. V.; Khomutova, Y. A.; Nesterov, I. D.; Ioffe, S. L. Synthesis 2004, 1159.
2. Cotel, G.; Denmark, S. E. Nitronates In The Chemistry of Heterocyclic Compounds, Vol. 59; Pawda, A.; Pearson, W. H., Eds.; J. Wiley & Sons Inc.: New York, 2002, 83-167.
3. Lapidus, A. L.; Eliseev, O. L.; Bondarenko, T. N.; Sizan, O. E.; Ostapenko, A. G.; Beletskaya, I. P. Synthesis 2002, 317.
4. 4: C, 65.96; H, 7.27; N, 4.81. Found: C, 66.20; H, 7.35; N, 4.75.
5. Hesse, M.; Meier, H.; Zeeh, B. Spektroskopische Methoden in der Organischen Chemie; Thieme: Stuttgart, 1995, 108.
6. Lambert, J. B.; Takeuchi, Y. Cyclic Organonitrogen Stereodynamics; VCH: New York, 1992, 170.
7. Juaristi, E. Enantioselective Synthesis of β-Amino Acids; Wiley-VCH: New York, 1996.
8. A few successful attempts to prepare α-amino acids from 3-methoxycarbonyl-5,6-dihydro-4H-1,2-oxazines and β-amino acids from 4-methoxycarbonyl-5,6-dihydro-4H-1,2-oxazines were reported previously, see: (a) Chrystal, E. J. T.; Gilchrist, T. L.; Stretch, W. J. Chem. Res., Synop. 1987, 180.
9. (b) Henning, R.; Lerch, U.; Urbach, H. Synthesis 1989, 265.
10. (c) Tishkov, A. A.; Reissig, H.-U.; Ioffe, S. L. Synlett 2002, 863.