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Publication details

Document type
Journal articles

Document subtype
Full paper

Title
An easy approach to dihydrochalcones via chalcone in situ hydrogenation

Participants in the publication
Ana R. Jesus (Author)
Ana P. Marques (Author)
Amélia P. Rauter (Author)
Dep. Química e Bioquímica
CQB - Centro de Química e Bioquímica 

Scope
International

Refereeing
Yes

Summary
Dihydrochalcones are polyphenols that exhibit a diversity of bioactivities, namely anti-inflammatory, antimicrobial and antiviral. We have explored the synthetic access to such molecular entities, and describe now an easy and scalable approach based on reduction of the olefinic double bond of chalcone precursors via in situ hydrogenation with the system Et3SiH-Pd/C in very high yield. The intermediate chalcones were synthesized also by a simple and efficient microwave-assisted Claisen–Schmidt condensation of aromatic aldehydes with acetophenones, conveniently protected with ethoxymethyl ether, if required. Chalcones were obtained as single reaction product in high yield in 2–3 h, while under conventional conditions at room temperature the reaction was carried out with completion only after 24 h. In addition, microwave irradiation has proven very efficient for deprotection of ethoxymethyl ether with iron chloride in only 10 min and very high yield.

Date of Publication
2016-04-01

Institution
FACULDADE DE CIÊNCIAS DA UNIVERSIDADE DE LISBOA

Where published
Pure and Applied Chemistry

Publication Identifiers
ISSN - 1365-3075

Publisher
Walter de Gruyter GmbH

Volume
88
Number
4

Number of pages
13
Starting page
349
Last page
361

Document Identifiers
DOI - https://doi.org/10.1515/pac-2016-0303
URL - http://dx.doi.org/10.1515/pac-2016-0303

Rankings
SCIMAGO Q1 (2016) - 1,032 - Chemistry (miscellaneous)

Keywords
dihydrochalcone Chemical synthesis ESOC-19 biomolecular chemistry chalcone aromatic compounds aldol reactions

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APA
Ana R. Jesus, Ana P. Marques, Amélia P. Rauter, (2016). An easy approach to dihydrochalcones via chalcone in situ hydrogenation. Pure and Applied Chemistry, 88, 349-361. ISSN 1365-3075. eISSN . http://dx.doi.org/10.1515/pac-2016-0303

IEEE
Ana R. Jesus, Ana P. Marques, Amélia P. Rauter, "An easy approach to dihydrochalcones via chalcone in situ hydrogenation" in Pure and Applied Chemistry, vol. 88, pp. 349-361, 2016. 10.1515/pac-2016-0303

BIBTEX
@article{38765, author = {Ana R. Jesus and Ana P. Marques and Amélia P. Rauter}, title = {An easy approach to dihydrochalcones via chalcone in situ hydrogenation}, journal = {Pure and Applied Chemistry}, year = 2016, pages = {349-361}, volume = 88 }