Cycloaddition of homophthalic anhydrides with aldehydes and ketones: a route to 3,4-dihydroisocoumarin-4-carboxylic acid derivatives

Autor:	André Tartar, Niefang Yu, Rebecca Poulain, Jean-Claude Gesquiere
Rok vydání:	1999
Předmět:	chemistry.chemical_classification Carboxylic acid fungi Organic Chemistry chemistry.chemical_element Ether Biochemistry Cycloaddition Benzaldehyde chemistry.chemical_compound chemistry Dihydroisocoumarin Yield (chemistry) Drug Discovery Organic chemistry Boron
Zdroj:	Tetrahedron. 55:13735-13740
ISSN:	0040-4020
Popis:	Homophthalic anhydride reacts with benzaldehyde in the presence of boron trifluoride-diethyl ether complex to give the cycloadduct 3-phenyl-3,4-dihydroisocoumarin-4-carboxylic acid in good to excellent yield. Under these conditions we did not observe the formation of Perkin-type products. The reaction can be extended to a wide variety of aldehydes and to some ketones in synthetically useful yields. Amides can be obtained in good yields after activation of the carboxylic function with DCC at O°C.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::6def0fb0ef0de9abcc9edbf2a5dd9bdf https://doi.org/10.1016/s0040-4020(99)00840-6 Zobrazit plný text záznamu Full Text from ScienceDirect