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

Francesco Risitano; Giovanni Grassi; Francesco Foti; Roberto Romeo

doi:10.1055/s-2002-19304

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

Francesco Risitano*^a, Giovanni Grassi^a, Francesco Foti^a, Roberto Romeo^b
^a Dipartimento di Chimica Organica e Biologica, Università, Vill. S.Agata, 98166 Messina, Italy
Fax: +39(90)393897; e-Mail: frisitan@isengard.unime.it;
^b Dipartimento Farmaco-chimico, Università, via SS Annunziata, 98100 Messina, Italy

Abstract

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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

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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

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.

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