MIRC Reactions of (E)-Chalcones with Azol-5-ones - A Diastereoselective Entry to Novel Spiro Tetrahydropyridine Derivatives

Abstract

Spiro tetrahydropyridine derivatives 4 and 5 were diastereoselectively prepared in good yield by reacting chalcones 3 with azolin-5-ones 1 and 2. From benzalacetones 10, the reaction occurred only with isoxazolin-5-ones 1 leading to spirans 11.

Key words

chalcones - spiro compounds - diastereoselectivity - Michael additions

References

• 1a Berger U. Dannhardt G. Obergrusberger R. Arch. Pharm.  1982,  428 
• 1b Dannhardt G. Sommer I. Arch. Pharm.  1985,  556 
• 1c Eicher T. Freihoff W. Synthesis  1986,  908 
• 1d Maison W. Lützen A. Kosten M. Schlemminger I. Westerhoff O. Martens J. J. Chem. Soc., Perkin Trans 1  1999,  3515 
• 1e Westerhoff O. Lützen A. Maison W. Kosten M. Martens J. J. Chem. Soc., Perkin Trans 1  2001,  508 
• 2a Stevens RV. In The Total Synthesis of Natural Products   Vol. 3:  ApSimon J. John Wiley; New York: 1977.  p.439-543 
• 2b Hua DH. Bharathi SN. Takusagawa F. Tsujimoto A. Panangadan JAK. Hung M.-H. Bravo AA. Erpelding AM. J. Org. Chem.  1989,  54:  5659 
• 2c Hua DH. Bharathi SN. Robinson PD. Tsujimoto A. J. Org. Chem.  1990,  34:  2128 
• 3 Maison W. Kosten M. Charpy A. Kintscher-Langenhagen J. Schlemminger I. Lützen A. Westerhoff O. Martens J. Eur. J. Org. Chem.  1999,  2433 
• 4 Fry DG. Fowler CB. Dieter RK. Synlett  1994,  836 
• 5 Risitano F. Grassi G. Bruno G. Nicolò F. Liebigs Ann.  1997,  441 
• 6 Risitano F. Grassi G. Foti F. Bilardo C. Tetrahedron  2000,  56:  9669 
• 7 Little RD. Dawson JR. Tetrahedron Lett.  1980,  21:  2609 
• 8a Knorr L. Klozt C. Ber.  1887,  20:  2545 
• 8b Ehsan E. Ali S. Ahmed N. Karimullah G. Pakistan J. Sci. Ind. Res.  1967,  10:  228 
• 10 Christoffers J. Eur. J. Org. Chem.  1998,  1259 
• 11 Risitano F. Grassi G. Caruso F. Foti F. Tetrahedron  1996,  1443 ; and references cited therein.
• 12 Shibasaki M. Sasai H. Arai T. Angew.Chem. Int. Ed. Engl.  1997,  1236 
• 13 Baldwin JE. J. Chem. Soc. Chem. Comm.  1976,  734 
• 14 Osman AN. Kandeel MM. Said MM. Ahmed EM. Indian J. Chem.  1996,  35B:  1073 

9

The use of substituted benzaldehydes in both these procedures was unsuccessful, indicating that steric or electronic factors can play a negative role in the transformations of 1 or 2 to 4 or 5 respectively, which is not the case with isoxazolin-5-one 1.