2-Nitrofurans as dienophiles in Diels-Alder reactions

Tetrahedron Letters

Volumn 46, Issue 50, 2005, Pages 8711-8714

  Rosa, Claudia Della ^a   Kneeteman, María N ^a   Mancini, Pedro M E ^a  

^a UNIVERSIDAD NACIONAL DEL LITORAL   (Argentina)

Author keywords

Diels Alder; Dienophiles; Nitrofurans

Indexed keywords

1,3 BUTADIENE DERIVATIVE; ACETIC ACID DERIVATIVE; ALKADIENE; CARBOXYLIC ACID DERIVATIVE; FURAN DERIVATIVE; NITROFURAN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOADDITION; DIELS ALDER REACTION; PHYSICAL CHEMISTRY; THERMAL CONDUCTIVITY;

BETULACEAE;

EID: 27744528039     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.10.042     Document Type: Article

References (12)

1. F. Fringuelli, and A. Taticchi Dienes in the Diels-Alder reaction 1990 Wiley Interscience New York pp 276-280
2. E. Wenkert, and S. Piettre J. Org. Chem. 53 1988 5850 5853
3. E. Wenkert, P. Moeller, and S. Piettre J. Am. Chem. Soc. 110 1988 7188 7194
4. B. Biolatto, M. Kneeteman, E. Paredes, and P. Mancini J. Org. Chem. 66 2001 3906
5. B. Biolatto, M. Kneeteman, and P. Mancini Tetrahedron Lett. 40 1999 3343 3346
6. E. Paredes, B. Biolatto, M. Kneeteman, and P. Mancini Tetrahedron Lett. 41 2000 8079 8982
7. E. Paredes, B. Biolatto, M. Kneeteman, and P. Mancini Tetrahedron Lett. 43 2002 4601 4603
8. E. Paredes, M. Kneeteman, M. Gonzalez Sierra, and P. Mancini Tetrahedron Lett. 44 2003 2943 2945
9. C. Della Rosa, E. Paredes, M. Kneeteman, and P. Mancini Lett. Org. Chem. 1 2004 369 371
10. Della Rosa, C.; Kneeteman, M.; Mancini, P. M. E., unpublished results.
11. General procedure. The temperature, the length of the reaction and the diene/dienophile ratio are given in Tables 1 and 2. An ampoule containing 1.0 mmol of the dienophile and the required amount of diene in 0.5 ml of dry benzene was cooled in liquid nitrogen, sealed and then heated in an oil bath. After the reaction time was completed, it was cooled once more in liquid nitrogen and opened. The solution was evaporated and the residue purified by column chromatography in silica gel or alumina using hexane/ethyl acetate mixtures as eluent. B. Biolatto, M. Kneeteman, E. Paredes, and P. Mancini J. Org. Chem. 66 2001 3906 3912
12. 3)