Science and Technology Production
Article
Authorship
Scoccia, Jimena
;
Castro, Maria Julia
;
Faraoni, María Belén
;
BOUZAT, CECILIA BEATRIZ
;
Martín García, Victor Sotero
;
GERBINO, DARIO CESAR
Date
2017
Publishing House and Editing Place
Pergamon-Elsevier Science Ltd
Magazine
TETRAHEDRON,
vol. 73
(pp. 2913-2922)
Pergamon-Elsevier Science Ltd
Summary
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SIGEVA
A novel and efficient synthesis of dibenzo[b,e]oxepin-11(6H)-ones by direct intramolecular ortho-acylation from readily available 2-(phenoxymethyl)benzoic acids was developed. The method takes advantage of a newly developed cooperative system consisting of sustainable FeCl2 and Cl2CHOCH3 as the key components. This methodology is compatible with a wide variety of functional groups in good to excellent yields and high regioselectivity. The synthetic application of new protocol was extended to th...
A novel and efficient synthesis of dibenzo[b,e]oxepin-11(6H)-ones by direct intramolecular ortho-acylation from readily available 2-(phenoxymethyl)benzoic acids was developed. The method takes advantage of a newly developed cooperative system consisting of sustainable FeCl2 and Cl2CHOCH3 as the key components. This methodology is compatible with a wide variety of functional groups in good to excellent yields and high regioselectivity. The synthetic application of new protocol was extended to the synthesis of known tricyclic drug doxepin as well as a small library of oxepin based derivatives. For the first time, the obtained dibenzo[b,e]oxepinone derivatives were evaluated for their biological activities on the free-living nematode Caenorhabditis elegans as an effective and cost-efficient model system for anthelmintic discovery.
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Key Words
DIBENZO[b,e]OXEPIN-11(6H)-ONESDOXEPINSYNTHETIC METHODOLOGYANTHELMINTIC ACTIVITYINTRAMOLECULAR ACYLATIONANTHELMINTIC ACTIVITY
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