4-Alkenyl-2-aminothiazoles: Smart Dienes for Polar [4 + 2] Cycloadditions

Alajarín, Mateo; Cabrera, Jose; Sanchez-Andrada, Pilar; Orenes, Raul-Angel; Pastor Vivero, Aurelia

Publication:
4-Alkenyl-2-aminothiazoles: Smart Dienes for Polar [4 + 2] Cycloadditions

dc.contributor.author	Alajarín, Mateo
dc.contributor.author	Cabrera, Jose
dc.contributor.author	Sanchez-Andrada, Pilar
dc.contributor.author	Orenes, Raul-Angel
dc.contributor.author	Pastor Vivero, Aurelia
dc.contributor.department	Química Orgánica
dc.date.accessioned	2021-11-03T17:40:52Z
dc.date.available	2021-11-03T17:40:52Z
dc.date.created	2012-12-06
dc.description.abstract	An exhaustive investigation on the [4+2] cycloadditions of 4-alkenyl-2-aminothiazoles with a wide range of dienophiles has been carried out. 4-Alkenyl-2-aminothiazoles act as good in-out dienes reacting with dienophiles bearing electron-withdrawing groups. The heteroannulations, typically conducted under mild conditions, are endo-selective when cyclic dienophiles are employed and regioselective when the reactions are conducted with non symmetric dienophiles. The endo-selective processes presumably take place by concerted but highly asynchronous mechanisms. By contrast, the low levels of endo selectivity and the lack of stereospecificity in the reactions with certain acyclic dienophiles point to a stepwise mechanism with a zwitterion as the most plausible intermediate. The course of the reaction changes when the highly reactive PTAD and TCNE are used as dienophiles since only addition products are obtained. Calculations of the HOMO and LUMO energy values of representative 4-alkenyl-2-aminothiazoles and the results of π-facial diastereoselective processes by using chiral substrates are also disclosed.	es
dc.format	application/pdf	es
dc.format.extent	15	es
dc.identifier.citation	European Journal Organic Chemistry, 2013, 474-489
dc.identifier.doi	10.1002/ejoc.201201185
dc.identifier.issn	1434-193X (print) 1099-0690 (web)
dc.identifier.uri	http://hdl.handle.net/10201/113642
dc.language	eng	es
dc.publisher	Wiley	es
dc.relation	Nombre del proyecto: Transferencias intramoleculares de hidruro promovidas por la hidricidad de funciones acetálicas y similares. Código: CTQ2008-05827/BQU. Agencia/entidad financiadora: Ministerio de Ciencia e Innovación. Ámbito Nacional. Proyectos de Investigación Fundamental no Orientada, Programa Nacional de Proyectos de Investigación Fundamental en el marco del Plan Nacional de I+D+i 2008-2011. Convocatoria 2008. Nombre del proyecto: Reagrupamientos [1,n]-H en heterocumulenos y preparación de nuevos [2]-rotaxanos y lanzaderas moleculares. Código: 08661/PI/08. Agencia/entidad financiadora: Fundación Séneca-CARM, Consejería de Educación, Ciencia e Investigación. Ámbito Regional. Ayudas para la realización de proyectos de investigación. Programa Séneca 2008. Convocatoria 2008.	es
dc.relation.publisherversion	https://chemistry-europe.onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.201201185	es
dc.rights	info:eu-repo/semantics/openAccess	es
dc.rights	Attribution-NonCommercial-NoDerivatives 4.0 Internacional	*
dc.rights.uri	http://creativecommons.org/licenses/by-nc-nd/4.0/	*
dc.subject	[4+2] Cycloadditions	es
dc.subject	Alkenylthiazoles	es
dc.subject	Heteroannulation	es
dc.subject	Extra-annular addition	es
dc.subject	Stepwise	es
dc.subject.other	CDU::5 - Ciencias puras y naturales::54 - Química::547 - Química orgánica	es
dc.title	4-Alkenyl-2-aminothiazoles: Smart Dienes for Polar [4 + 2] Cycloadditions	es
dc.type	info:eu-repo/semantics/article	es
dspace.entity.type	Publication	es