<?xml version="1.0" encoding="ISO-8859-1"?><article xmlns:mml="http://www.w3.org/1998/Math/MathML" xmlns:xlink="http://www.w3.org/1999/xlink" xmlns:xsi="http://www.w3.org/2001/XMLSchema-instance">
<front>
<journal-meta>
<journal-id>1870-249X</journal-id>
<journal-title><![CDATA[Journal of the Mexican Chemical Society]]></journal-title>
<abbrev-journal-title><![CDATA[J. Mex. Chem. Soc]]></abbrev-journal-title>
<issn>1870-249X</issn>
<publisher>
<publisher-name><![CDATA[Sociedad Química de México A.C.]]></publisher-name>
</publisher>
</journal-meta>
<article-meta>
<article-id>S1870-249X2025000400709</article-id>
<article-id pub-id-type="doi">10.29356/jmcs.v69i4.2343</article-id>
<title-group>
<article-title xml:lang="en"><![CDATA[Regioselective Functionalization and Diels-Alder Cycloadditions of Exocyclic Dienes in Five-membered Heterocycles]]></article-title>
</title-group>
<contrib-group>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Monroy-Flores]]></surname>
<given-names><![CDATA[Gustavo A.]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Montoya]]></surname>
<given-names><![CDATA[Pablo]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[García-González]]></surname>
<given-names><![CDATA[Ailyn N.]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Escalante]]></surname>
<given-names><![CDATA[Carlos H.]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Gutiérrez]]></surname>
<given-names><![CDATA[R. Uri]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Hernández]]></surname>
<given-names><![CDATA[R. Israel]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Fuentes-Benítes]]></surname>
<given-names><![CDATA[Aydeé]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
<xref ref-type="aff" rid="Aaf"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Barrera]]></surname>
<given-names><![CDATA[Edson]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Gómez-García]]></surname>
<given-names><![CDATA[Omar]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Delgado]]></surname>
<given-names><![CDATA[Francisco]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
<contrib contrib-type="author">
<name>
<surname><![CDATA[Tamariz]]></surname>
<given-names><![CDATA[Joaquín]]></given-names>
</name>
<xref ref-type="aff" rid="Aff"/>
</contrib>
</contrib-group>
<aff id="Af1">
<institution><![CDATA[,Instituto Politécnico Nacional Escuela Nacional de Ciencias Biológicas Departamento de Química Orgánica]]></institution>
<addr-line><![CDATA[México, D.F. ]]></addr-line>
<country>Mexico</country>
</aff>
<aff id="Af2">
<institution><![CDATA[,Universidad Autónoma del Estado de México Facultad de Química Departamento de Química Orgánica]]></institution>
<addr-line><![CDATA[Toluca Estado de México]]></addr-line>
<country>Mexico</country>
</aff>
<pub-date pub-type="pub">
<day>00</day>
<month>12</month>
<year>2025</year>
</pub-date>
<pub-date pub-type="epub">
<day>00</day>
<month>12</month>
<year>2025</year>
</pub-date>
<volume>69</volume>
<numero>4</numero>
<fpage>709</fpage>
<lpage>730</lpage>
<copyright-statement/>
<copyright-year/>
<self-uri xlink:href="http://www.scielo.org.mx/scielo.php?script=sci_arttext&amp;pid=S1870-249X2025000400709&amp;lng=en&amp;nrm=iso"></self-uri><self-uri xlink:href="http://www.scielo.org.mx/scielo.php?script=sci_abstract&amp;pid=S1870-249X2025000400709&amp;lng=en&amp;nrm=iso"></self-uri><self-uri xlink:href="http://www.scielo.org.mx/scielo.php?script=sci_pdf&amp;pid=S1870-249X2025000400709&amp;lng=en&amp;nrm=iso"></self-uri><abstract abstract-type="short" xml:lang="en"><p><![CDATA[Abstract. An acid-catalyzed regioselective addition of diverse nucleophiles to exo-oxazolidin-2-one dienes was presently carried out, leading to a series of functionalized 4-oxazolin-2-ones. The direct formylation of 4-methyl-4-oxazolin-2-ones provided the corresponding 5-formyl-4-oxazolin-2-ones, which were applied in the construction of the 4,5-dihydrobenzo[d]oxazolones through a Staunton-Weinreb annulation process. The reactivity of symmetrical and unsymmetrical exo-imidazolidin-2-one dienes was studied in Diels-Alder cycloadditions with dienophiles N-phenylmaleimide and benzyne. The aromatization of the [4+2] adducts led to the polycyclic benzo- and naphtho[d]imidazol-2-ones, which have potential pharmacological activity.]]></p></abstract>
<abstract abstract-type="short" xml:lang="es"><p><![CDATA[Resumen. Se describe la adición regioselectiva catalizada por ácido de diversos nucleófilos a los dienos exo-oxazolidinonas que conduce a una serie de 4-oxazolin-2-onas funcionalizadas. La formilación directa de 4-metil-4-oxazolidin-2-onas proporcionó las 5-formil-4-oxazolin-2-onas correspondientes, las cuales se emplearon en la construcción de las 4,5-dihidrobenzo[d]oxazolonas mediante un proceso de anillación de Staunton-Weinreb. Se estudió la reactividad de dienos exo-imidazolidin-2-onas simétricos y no simétricos en cicloadiciones de Diels-Alder con los dienófilos N-fenilmaleimida y bencino. La aromatización de los aductos [4+2] condujo a los benzo- y nafto[d]imidazol-2-onas policíclicas como compuestos con actividad farmacológica potencial.]]></p></abstract>
<kwd-group>
<kwd lng="en"><![CDATA[4,5-dimethylene-2-oxazolidinone dienes]]></kwd>
<kwd lng="en"><![CDATA[5-functionalized 4-oxazolin-2-ones]]></kwd>
<kwd lng="en"><![CDATA[4,5-dimethylene-2-imidazolidinone dienes]]></kwd>
<kwd lng="en"><![CDATA[Staunton-Weinreb annulation]]></kwd>
<kwd lng="en"><![CDATA[Diels-Alder reaction]]></kwd>
<kwd lng="es"><![CDATA[Dienos 4,5-dimetilen-2-oxazolidinonas]]></kwd>
<kwd lng="es"><![CDATA[4-oxazolin-2-onas 5-funcionalizadas]]></kwd>
<kwd lng="es"><![CDATA[dienos 4,5-dimetilen-2-imidazolidinonas]]></kwd>
<kwd lng="es"><![CDATA[anillación de Staunton-Weinreb]]></kwd>
<kwd lng="es"><![CDATA[reacción de Diels-Alder]]></kwd>
</kwd-group>
</article-meta>
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