Intramolecular cycloaddition of N-phthalimidoaziridines to double and triple carbon-carbon bonds

Tetrahedron Letters

Volumn 50, Issue 44, 2009, Pages 5990-5993

  Pankova, Alena S ^a   Voronin, Vladimir V ^a   Kuznetsov, Mikhail A ^a  

^a ST PETERSBURG STATE UNIVERSITY   (Russian Federation)

Author keywords

1,5 Dipolar electrocyclization; Azomethine ylide; Intramolecular 1,3 dipolar cycloaddition; N Phthalimidoaziridine

Indexed keywords

3 (2 ALLYLOXYPHENYL) 1 PHTHALIMIDOAZIRIDINE 2 CARBOXYLIC ACID; 3 (2 PROPARGYLOXYPHENYL) 1 PHTHALIMIDOAZIRIDINE 2 CARBOXYLIC ACID; 5 METHOXYOXAZOLE; AZIRIDINE DERIVATIVE; CARBON; CARBOXYLIC ACID DERIVATIVE; PHTHALIMIDOAZIRIDINE; PHTHALIMIDOPYRROLINE; PYRROLE DERIVATIVE; PYRROLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CYCLIZATION; CYCLOADDITION; STEREOSPECIFICITY;

EID: 70149122131     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.08.015     Document Type: Article

References (18)

1. Lown J.W. In: Padwa A. (Ed). 1,3-Dipolar Cycloaddition Chemistry (1984), John Wiley & Sons, New York 653-732
2. Harwood L.M., and Vickers R.J. In: Padwa A., and Pearson W.H. (Eds). Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products (2003), John Wiley & Sons, Hoboken 169-252
3. Coldham I., and Hufton R. Chem. Rev. 105 (2005) 2765-2809
4. Heine H.W., and Peavy R. Tetrahedron Lett. 35 (1965) 3123-3126
5. Foucaud A., and Baudru M. C. R. Acad. Sci. 271 C (1970) 1613-1615
6. Person H., Luanglath K., Baudru M., and Foucaud A. Bull. Soc. Chim. Fr. 11-12 (1976) 1989-1992
7. Charier J., Person H., and Foucaud A. Tetrahedron Lett. 16 (1979) 1381-1384
8. Charrier J., Foucaud A., Person H., and Loukakou E. J. Org. Chem. 48 (1983) 481-486
9. Kuznetsov M.A., Pankova A.S., Ushkov A.V., and Selivanov S.I. Russ. J. Org. Chem. 44 (2008) 1807-1815
10. Pankova A.S., Ushkov A.V., Kuznetsov M.A., and Selivanov S.I. Vestnik Sankt-Peterburgskogo Universiteta (Herold of Saint-Petersburg State University) Ser. 4 1 (2009) 150-154
11. Rossini M., Budriesi R., Bixel M.G., Bolognesi M.L., Chiarini A., Hucho F., Krogsgaard-Larsen P., Mellor A., Minarini I.R., Tumiatti V., Usherwood P.N.R., and Melchiorre C. J. Med. Chem. 42 (1999) 5212-5223
12. Confalone P.N., and Huie E.M. J. Am. Chem. Soc. 106 (1984) 7175-7178
13. The synthesis of compounds 1-4a,b will be described elsewhere.
14. Gladstone W.A.F., and Norman R.O.C. J. Chem. Soc. (C) (1966) 1536-1540
15. Atkinson R.S., and Kelly B.J. J. Chem. Soc., Perkin Trans. 1 (1989) 1627-1630
16. DeShong P., Kell D.A., and Silder D.R. J. Org. Chem. 50 (1985) 2309-2315
17. Atkinson R.S., and Malpass J.R. J. Chem. Soc., Perkin Trans. 1 (1977) 2242-2249
18. Beletsky E.V., and Kuznetsov M.A. Russ. J. Org. Chem. 45 (2009) 1237-1248