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Titolo:
Inverse electron demand Diels-Alder reactions of psoralens. Synthesis and mass spectra of novel pyridazinocoumarins
Autore:
Gonzalez, JC; Dedola, T; Santana, L; Uriarte, E; Begala, M; Copez, D; Podda, G;
Indirizzi:
Univ Santiago de Compostela, Fac Farm, Dept Quim Organ, Santiago De Compostela, Spain Univ Santiago de Compostela Santiago De Compostela Spain postela, Spain Univ Cagliari, Dipartimento Farmaco Chim Tecnol, Cagliari, Italy Univ Cagliari Cagliari Italy mento Farmaco Chim Tecnol, Cagliari, Italy
Titolo Testata:
JOURNAL OF HETEROCYCLIC CHEMISTRY
fascicolo: 4, volume: 37, anno: 2000,
pagine: 907 - 910
SICI:
0022-152X(200007/08)37:4<907:IEDDRO>2.0.ZU;2-T
Fonte:
ISI
Lingua:
ENG
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Physical, Chemical & Earth Sciences
Citazioni:
17
Recensione:
Indirizzi per estratti:
Indirizzo: Gonzalez, JC Univ Santiago de Compostela, Fac Farm, Dept Quim Organ, Santiago De Compostela, Spain Univ Santiago de Compostela Santiago De Compostela Spain n
Citazione:
J.C. Gonzalez et al., "Inverse electron demand Diels-Alder reactions of psoralens. Synthesis and mass spectra of novel pyridazinocoumarins", J HETERO CH, 37(4), 2000, pp. 907-910

Abstract

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 transesterification with release of methanol. The characterization of the products of these reactions by exhaustive mass spectrometric analysis is discussed.

ASDD Area Sistemi Dipartimentali e Documentali, Università di Bologna, Catalogo delle riviste ed altri periodici
Documento generato il 06/07/20 alle ore 08:09:57