Synthesis of 3,4-Dihydroquinazolinones via Base-Promoted Formal [4 + 2] Cycloadditions

3,4-dihydroquinazolin-2(1H)-one (3,4-DHQ) is a key structural motif found in many biologically active molecules. Although several synthetic methods have been developed to date, harsh reaction conditions, and/or metal toxic reagents are often required. In this work, a general, metal-free methodology...

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Autores: Torres Oya, Sergio|||0000-0002-1003-519X, Fernández Rodríguez, Manuel Ángel|||0000-0002-0120-5599, Zurro de la Fuente, Mercedes|||0000-0003-1222-7926
Formato: artículo
Fecha de publicación:2025
País:España
Recursos:Universidad de Alcalá (UAH)
Repositorio:e_Buah Biblioteca Digital Universidad de Alcalá
Idioma:inglés
OAI Identifier:oai:ebuah.uah.es:10017/66138
Acesso em linha:http://hdl.handle.net/10017/66138
https://dx.doi.org/10.1002/adsc.70056
Access Level:acceso abierto
Palavra-chave:3,4-dihydroquinazolinones
[4 þ 2] cycloadditions
Aza-ortho-quinone methides
Isocyanates
Química
Chemistry
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repository_id_str
spelling Synthesis of 3,4-Dihydroquinazolinones via Base-Promoted Formal [4 + 2] CycloadditionsTorres Oya, Sergio|||0000-0002-1003-519XFernández Rodríguez, Manuel Ángel|||0000-0002-0120-5599Zurro de la Fuente, Mercedes|||0000-0003-1222-79263,4-dihydroquinazolinones[4 þ 2] cycloadditionsAza-ortho-quinone methidesIsocyanatesQuímicaChemistry3,4-dihydroquinazolin-2(1H)-one (3,4-DHQ) is a key structural motif found in many biologically active molecules. Although several synthetic methods have been developed to date, harsh reaction conditions, and/or metal toxic reagents are often required. In this work, a general, metal-free methodology for the synthesis of 3,4-DHQs is described. This novel protocol relies on a formal [4 + 2] cycloaddition of in situ formed aza-ortho-quinone methides and isocyanates leading to a wide variety of 3,4-DHQs in yields up to 98%.Wiley20252025-08-16journal articlehttp://purl.org/coar/resource_type/c_6501NAhttp://purl.org/coar/version/c_be7fb7dd8ff6fe43info:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10017/66138https://dx.doi.org/10.1002/adsc.70056reponame:e_Buah Biblioteca Digital Universidad de Alcaláinstname:Universidad de Alcalá (UAH)Inglésengopen accesshttp://purl.org/coar/access_right/c_abf2Attribution-NonCommercial-NoDerivatives 4.0 Internationalhttp://creativecommons.org/licenses/by-nc-nd/4.0/info:eu-repo/semantics/openAccessoai:ebuah.uah.es:10017/661382026-06-18T11:13:07Z
dc.title.none.fl_str_mv Synthesis of 3,4-Dihydroquinazolinones via Base-Promoted Formal [4 + 2] Cycloadditions
title Synthesis of 3,4-Dihydroquinazolinones via Base-Promoted Formal [4 + 2] Cycloadditions
spellingShingle Synthesis of 3,4-Dihydroquinazolinones via Base-Promoted Formal [4 + 2] Cycloadditions
Torres Oya, Sergio|||0000-0002-1003-519X
3,4-dihydroquinazolinones
[4 þ 2] cycloadditions
Aza-ortho-quinone methides
Isocyanates
Química
Chemistry
title_short Synthesis of 3,4-Dihydroquinazolinones via Base-Promoted Formal [4 + 2] Cycloadditions
title_full Synthesis of 3,4-Dihydroquinazolinones via Base-Promoted Formal [4 + 2] Cycloadditions
title_fullStr Synthesis of 3,4-Dihydroquinazolinones via Base-Promoted Formal [4 + 2] Cycloadditions
title_full_unstemmed Synthesis of 3,4-Dihydroquinazolinones via Base-Promoted Formal [4 + 2] Cycloadditions
title_sort Synthesis of 3,4-Dihydroquinazolinones via Base-Promoted Formal [4 + 2] Cycloadditions
dc.creator.none.fl_str_mv Torres Oya, Sergio|||0000-0002-1003-519X
Fernández Rodríguez, Manuel Ángel|||0000-0002-0120-5599
Zurro de la Fuente, Mercedes|||0000-0003-1222-7926
author Torres Oya, Sergio|||0000-0002-1003-519X
author_facet Torres Oya, Sergio|||0000-0002-1003-519X
Fernández Rodríguez, Manuel Ángel|||0000-0002-0120-5599
Zurro de la Fuente, Mercedes|||0000-0003-1222-7926
author_role author
author2 Fernández Rodríguez, Manuel Ángel|||0000-0002-0120-5599
Zurro de la Fuente, Mercedes|||0000-0003-1222-7926
author2_role author
author
dc.subject.none.fl_str_mv 3,4-dihydroquinazolinones
[4 þ 2] cycloadditions
Aza-ortho-quinone methides
Isocyanates
Química
Chemistry
topic 3,4-dihydroquinazolinones
[4 þ 2] cycloadditions
Aza-ortho-quinone methides
Isocyanates
Química
Chemistry
description 3,4-dihydroquinazolin-2(1H)-one (3,4-DHQ) is a key structural motif found in many biologically active molecules. Although several synthetic methods have been developed to date, harsh reaction conditions, and/or metal toxic reagents are often required. In this work, a general, metal-free methodology for the synthesis of 3,4-DHQs is described. This novel protocol relies on a formal [4 + 2] cycloaddition of in situ formed aza-ortho-quinone methides and isocyanates leading to a wide variety of 3,4-DHQs in yields up to 98%.
publishDate 2025
dc.date.none.fl_str_mv 2025
2025-08-16
dc.type.none.fl_str_mv journal article
http://purl.org/coar/resource_type/c_6501
NA
http://purl.org/coar/version/c_be7fb7dd8ff6fe43
dc.type.openaire.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10017/66138
https://dx.doi.org/10.1002/adsc.70056
url http://hdl.handle.net/10017/66138
https://dx.doi.org/10.1002/adsc.70056
dc.language.none.fl_str_mv Inglés
eng
language_invalid_str_mv Inglés
language eng
dc.rights.none.fl_str_mv open access
http://purl.org/coar/access_right/c_abf2
Attribution-NonCommercial-NoDerivatives 4.0 International
http://creativecommons.org/licenses/by-nc-nd/4.0/
dc.rights.openaire.fl_str_mv info:eu-repo/semantics/openAccess
rights_invalid_str_mv open access
http://purl.org/coar/access_right/c_abf2
Attribution-NonCommercial-NoDerivatives 4.0 International
http://creativecommons.org/licenses/by-nc-nd/4.0/
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Wiley
publisher.none.fl_str_mv Wiley
dc.source.none.fl_str_mv reponame:e_Buah Biblioteca Digital Universidad de Alcalá
instname:Universidad de Alcalá (UAH)
instname_str Universidad de Alcalá (UAH)
reponame_str e_Buah Biblioteca Digital Universidad de Alcalá
collection e_Buah Biblioteca Digital Universidad de Alcalá
repository.name.fl_str_mv
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