6-Hydroxyaurone aminomethyl derivatives in the inverse electron-demand Diels–Alder reaction

• Published in: Chemistry of heterocyclic compounds (New York, N.Y. 1965) Vol. 55; no. 12; pp. 1179 - 1184
• Main Authors: Popova, Antonina V., Mrug, Galyna P., Bondarenko, Svitlana P., Frasinyuk, Mikhaylo S.
• Format: Journal Article
• Language: English
• Published: New York Springer US 01.12.2019; Springer Nature; Springer; Springer Nature B.V
• Subjects: Chemical synthesis; Chemistry; Chemistry and Materials Science; Chemistry, Organic; Cycloaddition; Derivatives; Diels-Alder reaction; Diels-Alder reactions; Esters; Heterocyclic compounds; Organic Chemistry; Pharmacy; Physical Sciences; Quinone; Quinones; Science & Technology; Transformations; quinone methide; aurone; vinyl ether; Mannich base; Diels–Alder reaction; enamine; FUNGUS XYLARIA SP; O-QUINONE METHIDES; GENERATION; o-quinone methide; Diels-Alder reaction; PRECURSORS
• ISSN: 0009-3122; 1573-8353
• DOI: 10.1007/s10593-019-02598-z

The transformations of 7-dimethylaminomethyl-6-hydroxyaurone and 5-dimethylaminomethyl-6-hydroxy-7-methylurone in the inversed electron-demand hetero-Diels–Alder reaction were studied. As a result of in situ thermal formation of o -quinone methides containing the benzofuranone moiety and cycloaddition of cyclic vinyl esters, 2-benzylidene derivatives of difuro[2,3- b :2',3'- f ]chromen-3(2 H )-one, furo[2,3- f ]pyrano[2,3- b ]chromen-3(2 H )-one, difuro[2,3- b :3',2'- g ]chromen-3(2 H )-one, and furo[3,2- g ]pyrano[2,3- b ]chromen-3(2 H )-one heterocyclic systems were synthesized. A similar reaction with cyclic enamines, accompanied by subsequent transformation of hemi-aminals, led to the formation of partially hydrogenated derivatives of furo[2,3- a ]xanthen-3(2 H )-one and furo[3,2- b ]xanthen-3(2 H )-one.