Journal
BULLETIN OF THE KOREAN CHEMICAL SOCIETY
Volume 32, Issue 1, Pages 65-70Publisher
KOREAN CHEMICAL SOC
DOI: 10.5012/bkcs.2011.32.1.65
Keywords
Dihydrocoumarin; Chalcone; Aryl cinnamate; Fries rearrangement; Pechmann condensation
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Funding
- Ministry of Education, Science and Technology [2010-0029642]
- Korea Institute for Advancement of Technology (KIAT) [4R09-0301-003-S000100]
- National Research Foundation of Korea [4R09-0301-003-S000100] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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Coumarins are ubiquitous in plant kingdom and have been used as antitumor, antifungals, anticoagulants, insecticides. Chalcones are also widespread in plant kingdom and have been known to possess diverse biological activities; antibacterial, antifungal, antitumor and anti-inflammatory, etc. As they are considered as important natural products, numerous synthetic approaches have been reported up to the present. We devise a new selective method of preparing dihydrocoumarins and chalcones from aryl cinnamates by the selection of reagents. Dihydrocoumarin derivatives were prepared selectively by using intramolecular cyclization catalyzed by p-toluene sulfonic acid. Also, chalcones were prepared by Fries-rearrangement catalyzed by TiCl(4). This method can be used for preparing various coumarin & chalcone compounds.
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