α-Acylaminophosphonates possessing epoxyisoindolone moiety

Tetrahedron

Volumn 63, Issue 51, 2007, Pages 12576-12582

  Kachkovskyi, Georgiy O ^a   Kolodiazhnyi, Oleg I ^a  

^a INSTITUTE OF BIOORGANIC CHEMISTRY AND PETROCHEMISTRY   (Ukraine)

Author keywords

Aminophosphonates; Epoxyisoindolones; Tandem acylation 4+2 cycloaddition reaction

Indexed keywords

DIMETHYL 1 [3 AZA 6 CARBOXY 10 OXA EXO TRICYCLO[5.2.1.0 1,5] 4 OXODEC 8 EN 3 YL) 1 (4 FLUOROPHENYL)METHYLPHOSPHONATE; DIMETHYL 1 [3 AZA 6 CARBOXY 10 OXA EXO TRICYCLO[5.2.1.0 1,5] 4 OXODEC 8 EN 3 YL) 1 (FURYL)METHYLPHOSPHONATE; DIMETHYL 1 [3 AZA 6 CARBOXY 10 OXA EXO TRICYCLO[5.2.1.0 1,5] 4 OXODEC 8 EN 3 YL) 1 PHENYLMETHYLPHOSPHONATE; DIMETHYL 1 [3 AZA 6 CARBOXY 10 OXA EXO TRICYCLO[5.2.1.0 1,5] 4 OXODEC 8 EN 3 YL) 1 PIPERONYLMETHYLPHOSPHONATE; DIMETHYL 3 AZA 6 CARBOXY 10 OXA EXO TRICYCLO[5.2.1.0 1,5] 4 OXODEC 8 EN 3 YLMETHYLPHOSPHONATE; DIMETHYL N (4 FLUOROPHENYLMETHYL) 3 AZA 6 CARBOXY 10 OXA EXO TRICYCLO[5.2.1.0 1,5] 4 OXODEC 8 EN 2 YL ENDO PHOSPHONATE; DIMETHYL N [(2 FURYL)METHYL] 3 AZA 6 CARBOXY 10 OXA EXO TRICYCLO[5.2.1.0 1,5] 4 OXODEC 8 EN 2 YL ENDO PHOSPHONATE; DIMETHYL N BENZYL 3 AZA 6 CARBOXY 10 OXA EXO TRICYCLO[5.2.1.0 1,5] 4 OXODEC 8 EN 2 YL ENDO PHOSPHONATE; DIMETHYL N METHYL 3 AZA 6 CARBOXY 10 OXA EXO TRICYCLO[5.2.1.0 1,5] 4 OXODEC 8 EN 2 YL ENDO PHOSPHONATE; DIMETHYL N PIPERONYLMETHYL 3 AZA 6 CARBOXY 10 OXA EXO TRICYCLO[5.2.1.0 1,5] 4 OXODEC 8 EN 2 YL ENDO PHOSPHONATE; PHOSPHORAMIDIC ACID; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; CRYSTAL STRUCTURE; CYCLOADDITION; DRUG ISOLATION; DRUG STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 35748931778     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.10.022     Document Type: Article

References (33)

1. Mastalerz P., and Kafarski P. Naturally Occurring Aminophosphonic and Aminophosphinic Acids. In: Kukhar V.P., and Hudson H.R. (Eds). Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity (2000), John Wiley, New York, NY 1-32
2. Pratt R.F. Science 246 (1989) 917-919
3. Mikolajczyk M., Drabowicz J., and Lyzwa P. Asymmetric Synthesis of Phosphonic Analogs of β-Amino Acids. In: Juaristi E., and Soloshonok V.A. (Eds). Enantioselective Synthesis of Beta-Amino Acids (2005), John Wiley, New York, NY 261-277
4. Kolodiazhnyi O.I. Tetrahedron: Asymmetry 16 (2005) 3295-3340
5. Kolodiazhnyi O.I. Russ. Chem. Rev. 75 (2006) 227-253
6. Migianu, E.; Even, P.; Monteil, P.; Lecouvey, M. The 16th International Conference on Phosphorus Chemistry (Abstract of Reports), Birmingham, 2004; p 173.
7. Beers S.A., Schwender C.F., Loughney D.A., Malloy E., Demarest K., and Jordan J. Bioorg. Med. Chem. 4 (1996) 1693-1701
8. Kaplan A.P., and Barlett P.A. Biochemistry 30 (1991) 8165-8170
9. Kafarski P., and Lejczak B. Curr. Med. Chem. Anti-Cancer Agents 1 (2001) 301-312
10. Mikolajczyk M. J. Organomet. Chem. 690 (2005) 2488-2496
11. Meyer F., Laaziri A., Papini A.M., Uziel J., and Juge S. Tetrahedron 60 (2004) 3593-3597
12. Firestone R.A., Maciejewicz N.S., Ratcliffe R.W., and Christensen B.G. J. Org. Chem. 39 (1974) 437
13. Cama L.D., and Christensen B.G. J. Am. Chem. Soc. 96 (1974) 7582-7584
14. Paulvannan K., and Jacobs J.W. Tetrahedron 55 (1999) 7433-7440
15. Zubkov F.I., Nikitina E.V., and Varlamov A.V. Russ. Chem. Rev. 74 (2005) 639-669
16. Bolotukhina E.V., Zubkov F.I., Nikitina E.V., and Varlamov A.V. Synthesis (2005) 1859-1875
17. Kouznetsov V.V., Cruz U.M., Zubkov F.I., and Nikitina E.V. Synthesis (2007) 375-384
18. Zylber J., Tubul A., and Brun P. Tetrahedron: Asymmetry 6 (1995) 377-380
19. Bolotukhina E.V., Zubkov F.I., and Varlamov A.V. Chem. Heterocycl. Comp. (2006) 963-994
20. Bolotukhina E.V., Zubkov F.I., and Varlamov A.V. Chem. Heterocycl. Comp. (2006) 1123-1157
21. Valencia E., Weiss I., Firdous S., Freyer A.J., and Shamma M. Tetrahedron 40 (1984) 3957-3962
22. Sarang P.S., Yavad A.A., Patil P.S., Krishna U.M., Trivedi G.K., and Salunkhe M.M. Synthesis (2007) 1091-1095
23. Kachkovskiy G.A., Andrushko N.V., Sheiko S.Yu., and Kolodiazhnyi O.I. Russ. J. Gen. Chem. 75 (2005) 1735-1743
24. Kabachnik M.I., and Medved' T.Ya. Dokl. Akad. Nauk SSSR (1952) 689
25. Chem. Abstr. 47 (1953) 2724b
26. Cherkasov R.A., and Galkin V.I. Russ. Chem. Rev. 67 (1998) 857-882
27. Boduszek B. Phosphorus, Sulfur Silicon Relat. Elem. 104 (1995) 63-70
28. Hägele G. Physical Properties and NMR-Spectroscopic Characterization of Aminophosphonates and Aminophosphinates. In: Kukhar V.P., and Hudson H.R. (Eds). Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity (2000), John Wiley, New York, NY 217-285
29. Nelson J.H. Coord. Chem. Rev. 139 (1995) 245-280
30. Griffiths D.V., and Griffiths P.A. NMR Data of Four Coordinated Phosphorus Compounds. In: Tebby J.C. (Ed). CRC Handbook of Phosphorus-31 Nuclear Magnetic Resonance Data (1991), CRC, Boston, MA 477-495
31. In: Verkade J.G., and Quin L.D. (Eds). Phosphorus-31 NMR Spectroscopy in Stereochemical Analysis (Methods in Stereochemical Analysis) (1994), John Wiley, New York, NY
32. Kraicheva I., Liogonkii B.I., Stefanova R., and Borisov G. Phosphorus Sulfur Relat. Elem. 40 (1988) 145-148
33. Kraicheva I., Stefanova R., and Borisov G. Phosphorus, Sulfur Silicon Relat. Elem. 79 (1993) 107-111