Hetero-Diels-Alder (HDA) Strategy for the Preparation of 6-Aryl- and Heteroaryl-Substituted Piperidin-2-one Scaffolds: Experimental and Theoretical Studies
| Autor: | Mauro Panunzio, Elisa Bandini, Antonio D'Aurizio, Sha Long, Alessandro Venturini, Magda Monari |
|---|---|
| Přispěvatelé: | S. Long, M. Monari, M. Panunzio, E. Bandini, A. D’Aurizio, A. Venturini |
| Rok vydání: | 2011 |
| Předmět: |
DENSITY FUNCTIONAL CALCULATIONS
Aryl Organic Chemistry Ring (chemistry) STEREOSELECTIVE-SYNTHESIS chemistry.chemical_compound 3-DIENES PIPERIDONES AZADIENES ALDEHYDES ACIDS Cyclo addition Microwave chemistry chemistry Computational chemistry SATURATED NITROGEN-HETEROCYCLES 4+2 CYCLOADDITION REACTIONS GENERAL-ROUTE 2-AZA-1 Diels alder NITROGEN HETEROCYCLES Physical and Theoretical Chemistry |
| Zdroj: | European journal of organic chemistry (Online) (2011): 6218–6225. doi:10.1002/ejoc.201100930 info:cnr-pdr/source/autori:Long, S. ; Monari, M. ; Panunzio, M.; Bandini, E. ; D'Aurizio, A.; Venturini, A./titolo:Hetero-Diels-Alder (HDA) Strategy for the Preparation of 6-Aryl-and Heteroaryl-Substituted Piperidin-2-one Scaffolds: Experimental and Theoretical Studies/doi:10.1002%2Fejoc.201100930/rivista:European journal of organic chemistry (Online)/anno:2011/pagina_da:6218/pagina_a:6225/intervallo_pagine:6218–6225/volume |
| ISSN: | 1434-193X |
| DOI: | 10.1002/ejoc.201100930 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Plný text