Synthesis 2002(1): 0116-0120
DOI: 10.1055/s-2002-19304
PAPER
© Georg Thieme Verlag Stuttgart · New York

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

Francesco Risitano*a, Giovanni Grassia, Francesco Fotia, Roberto Romeob
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
Further Information

Publication History

Received 16 August 2001
Publication Date:
04 August 2004 (online)

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.

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.