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.

chalcones - spiro compounds - diastereoselectivity - Michael additions

References

<A NAME="RT08201SS-1A">1a</A> Berger U. Dannhardt G. Obergrusberger R. Arch. Pharm.  1982,  428 

<A NAME="RT08201SS-1B">1b</A> Dannhardt G. Sommer I. Arch. Pharm.  1985,  556 

<A NAME="RT08201SS-1C">1c</A> Eicher T. Freihoff W. Synthesis  1986,  908 

<A NAME="RT08201SS-1D">1d</A> Maison W. Lützen A. Kosten M. Schlemminger I. Westerhoff O. Martens J. J. Chem. Soc., Perkin Trans 1  1999,  3515 

<A NAME="RT08201SS-1E">1e</A> Westerhoff O. Lützen A. Maison W. Kosten M. Martens J. J. Chem. Soc., Perkin Trans 1  2001,  508 

<A NAME="RT08201SS-2A">2a</A> Stevens RV. In The Total Synthesis of Natural Products   Vol. 3:  ApSimon J. John Wiley; New York: 1977.  p.439-543 

<A NAME="RT08201SS-2B">2b</A> Hua DH. Bharathi SN. Takusagawa F. Tsujimoto A. Panangadan JAK. Hung M.-H. Bravo AA. Erpelding AM. J. Org. Chem.  1989,  54:  5659 

<A NAME="RT08201SS-2C">2c</A> Hua DH. Bharathi SN. Robinson PD. Tsujimoto A. J. Org. Chem.  1990,  34:  2128 

<A NAME="RT08201SS-3">3</A> Maison W. Kosten M. Charpy A. Kintscher-Langenhagen J. Schlemminger I. Lützen A. Westerhoff O. Martens J. Eur. J. Org. Chem.  1999,  2433 

<A NAME="RT08201SS-4">4</A> Fry DG. Fowler CB. Dieter RK. Synlett  1994,  836 

<A NAME="RT08201SS-5">5</A> Risitano F. Grassi G. Bruno G. Nicolò F. Liebigs Ann.  1997,  441 

<A NAME="RT08201SS-6">6</A> Risitano F. Grassi G. Foti F. Bilardo C. Tetrahedron  2000,  56:  9669 

<A NAME="RT08201SS-7">7</A> Little RD. Dawson JR. Tetrahedron Lett.  1980,  21:  2609 

<A NAME="RT08201SS-8A">8a</A> Knorr L. Klozt C. Ber.  1887,  20:  2545 

<A NAME="RT08201SS-8B">8b</A> Ehsan E. Ali S. Ahmed N. Karimullah G. Pakistan J. Sci. Ind. Res.  1967,  10:  228 

<A NAME="RT08201SS-9">9</A>

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.

<A NAME="RT08201SS-10">10</A> Christoffers J. Eur. J. Org. Chem.  1998,  1259 

<A NAME="RT08201SS-11">11</A> Risitano F. Grassi G. Caruso F. Foti F. Tetrahedron  1996,  1443 ; and references cited therein.

<A NAME="RT08201SS-12">12</A> Shibasaki M. Sasai H. Arai T. Angew.Chem. Int. Ed. Engl.  1997,  1236 

<A NAME="RT08201SS-13">13</A> Baldwin JE. J. Chem. Soc. Chem. Comm.  1976,  734 

<A NAME="RT08201SS-14">14</A> Osman AN. Kandeel MM. Said MM. Ahmed EM. Indian J. Chem.  1996,  35B:  1073