Diels-Alder reactions of 2 '-hydroxychalcones with ortho-benzoquino-dimethane: A new synthesis of 3-aryl-2-naphthyl 2-hydroxyphenyl ketones

• Type: Article in International Scientific Journal
• Date: 2006

Authors

Brito, CM (Author) Other; Pinto, DCGA (Author) Other; Silva, AMS (Author) Other; Silva, AMG (Author) Other; Tome, AC (Author) Other; Cavaleiro, JAS (Author) Other

Journal

Title: European Journal of Organic Chemistry

Vol. 2006

Pages: 2558-2569

ISSN: 1434-193X

Publisher: Wiley-Blackwell

Indexing

ISI Web of Knowledge - 24 Citations

Scopus - 24 Citations

Other information

Authenticus ID: P-004-KQB

DOI: 10.1002/ejoc.200500872

Abstract (EN): Diels-Alder reactions of the 2'-hydroxychalcones 1a-e with ortho-benzoquinodimethane (3) yielded the 3-aryl-1,2,3,4-tetrahydro-2-naphthyl 2-hydroxyphenyl ketones 4a-e in good yields. The dehydrogenation of the cycloadducts 4a-e to 3-aryl-2-naphthyl 2-hydroxyphenyl ketones 5a-e was studied. Good results were obtained when DDQ was used as oxidant and microwave irradiation as energy source. Several benzoxanthone derivatives were also obtained as minor products. Structures of all new compounds were established by extensive NMR studies.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 12