Increased formation of oxepanes in non-aqueous medium in the cycloaddition of 3-O-allyl-1,2-isopropylidenefuranose N-Ph nitrones

Tetrahedron Letters

Volumn 49, Issue 18, 2008, Pages 2935-2938

  Datta, Seema ^a   Nath, Madhumita ^a   Chowdhury, Sandip ^a   Bhattacharjya, Anup ^a  

^a INDIAN INSTITUTE OF CHEMICAL BIOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

3 O ALLYL 1,2 ISOPROPYLIDENEFURANOSE N PH NITRONE DERIVATIVE; NITRONE DERIVATIVE; OXEPANE DERIVATIVE; PYRAN; UNCLASSIFIED DRUG;

AQUEOUS SOLUTION; ARTICLE; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; SYNTHESIS;

EID: 41549159665     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.03.014     Document Type: Article

References (11)

1. Gothelf K.V., and Jorgensen K.A. Chem. Rev. 98 (1998) 863
2. Osborn H.M.I., Gemmell N., and Harwood L.M. J. Chem. Soc., Perkin Trans. 1 (2002) 2419
3. Frederickson M. Tetrahedron 53 (1997) 403
4. Bhattacharjee A., Datta S., Chattopadhyay P., Ghoshal N., Kundu A.P., Pal A., Mukhopadhyay R., Chowdhury S., Bhattacharjya A., and Patra A. Tetrahedron 59 (2003) 4623 and references cited therein
5. Ghorai S., Mukhopadhyay R., Kundu A.P., and Bhattacharjya A. Tetrahedron 61 (2005) 2999
6. Shing T.K.M., and Zhong Y.-L. Tetrahedron 57 (2001) 1573
7. Shing T.K.M., Fung W.-C., and Wong C.-H. J. Chem. Soc., Chem. Commun. (1994) 449
8. Sharma G.V.M., Reddy K.R., Sankar A.R., and Kunwar A.C. Tetrahedron Lett. 42 (2001) 8893
9. Chatterjee A., and Bhattacharya P.K. J. Org. Chem. 71 (2006) 345
10. General experimental procedure for nitrone cycloaddition. A solution of the aldehyde 2 (1.5 mmol) and PhNHOH (2.2 mmol) in benzene (12 ml) containing 3 Å molecular sieves (2.5 g) was heated at reflux for 5 h. The mixture was then filtered, and the residue obtained after removal of the solvent from the filtrate was chromatographed over Si-gel (100-200 mesh) to afford the products.
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