Ring Opening Reactions of 3-Phosphonocoumarin Under Michael Reaction Conditions

Autor:	Nevena I. Petkova, Rositca D. Nikolova, Eleonora D. Ilieva
Rok vydání:	2011
Předmět:	Chemistry Organic Chemistry Diethyl ester chemistry.chemical_element Ring (chemistry) Biochemistry Sulfur Inorganic Chemistry chemistry.chemical_compound Nef reaction Nucleophile Michael reaction Organic chemistry Rearrangement reaction Piperidine
Zdroj:	Phosphorus, Sulfur, and Silicon and the Related Elements. 187:39-50
ISSN:	1563-5325 1042-6507
DOI:	10.1080/10426507.2011.571225
Popis:	From the Michael addition reaction of CH3NO2 to the diethyl ester of coumarin-3-phosphonic acid 1 in the presence of a base—KF or a nucleophilic agent (HNu = EtOH, piperidine, PrNH2)—the esters and amides 2, 4, and 5 were isolated. In order to avoid ring opening and to isolate only the product of the Michael addition reaction 3, the reaction was performed in the absence of a nucleophilic agent. In this case only, the product 3—a 2-oxochromane—was isolated. When the reaction was carried out in the presence of amines (Et3N, piperidine), a new product—1-hydroxy-4-(2′-hydroxyphenyl)-2,5-dioxopyrrolidin-3-yl-phosphonate 6—was formed by a new rearrangement reaction. [Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements for the following free supplemental resource: .cif files.]
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::ca72f8e8a39d5c7d5e27118bb7f14714 https://doi.org/10.1080/10426507.2011.571225 Zobrazit plný text záznamu