ChemInform Abstract: Inverse Electron Demand Diels-Alder Reactions of Psoralens. Synthesis and Mass Spectra of Novel Pyridazinocoumarins

Autor:	Eugenio Uriarte, Gianni Podda, José Carlos Otero González, Teresa Dedola, Debora Copez, Michela Begala, Lourdes Santana
Rok vydání:	2001
Předmět:	chemistry.chemical_classification Diene Double bond General Medicine Ring (chemistry) Pyrone chemistry.chemical_compound chemistry Computational chemistry Furan Intramolecular force Mass spectrum Organic chemistry Methanol
Zdroj:	ChemInform. 32
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.200102146
Popis:	Diels-Alder reactions between the furan double bond of 8-methoxypsoralen and 1,2,4,5-tetrazine or 3,6-bistrifluoromethyl-1,2,4,5-tetrazine were accompanied by the release of diatomic nitrogen and the opening of the furan ring to leave a 6-pyridazinocoumarin. When 3,6-bis(methoxycarbonyl)-1,2,4,5-tetrazine was used as diene with 8-methoxy-, 5-methoxy- or 8-hydroxypsoralen as substrate a previously unknown heterocyclic framework was created. Formation of the fourth ring was accompanied by conversion of the furan ring to a pyrone, presumably by intramolecular transestenfication with release of methanol. The characterization of the products of these reactions by exhaustive mass spectrometric analysis is discussed.
Databáze:	OpenAIRE
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