Preparation of piperidine-2-one scaffolds by the hetero-Diels-Alder (HAD) reaction, assisted by microwaves, is described. The versatility of this new approach has been demonstrated by the synthesis of racemic (+/-)-2-phenylpiperidine. Theoretical calculations have allowed us to clarify the factors that govern ring closure to form four-membered rings, arising from a Staudinger-type electrocyclization, and/or six-membered rings through a classical [4+2] HAD cyclization. This competition may be lowered by increasing the electronic demand of the dienophile, as anticipated by the computational studies

Hetero Diels-Alder (HDA) Strategy for the Preparation of 6-Aromatic- and Heteroaromatic-Substituted Piperidin-2-one Scaffold: Experimental and Theoretical Studies

MONARI, MAGDA;
2011

Abstract

Preparation of piperidine-2-one scaffolds by the hetero-Diels-Alder (HAD) reaction, assisted by microwaves, is described. The versatility of this new approach has been demonstrated by the synthesis of racemic (+/-)-2-phenylpiperidine. Theoretical calculations have allowed us to clarify the factors that govern ring closure to form four-membered rings, arising from a Staudinger-type electrocyclization, and/or six-membered rings through a classical [4+2] HAD cyclization. This competition may be lowered by increasing the electronic demand of the dienophile, as anticipated by the computational studies
2011
S. Long; M. Monari; M. Panunzio; E. Bandini; A. D’Aurizio; A. Venturini;
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/112866
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