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Aktivierte Chinone: regiospezifische Synthesen von substituierten Dibenzo [ b , d ]pyran‐6‐onen und Benzo [ b ]naphtho [ d ]pyran‐6‐onen
Author(s) -
Müller Peter,
Venakis Thomas,
Eugster Conrad Hans
Publication year - 1979
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19790620834
Subject(s) - chemistry , pyran , benzoquinone , phenols , medicinal chemistry , stereochemistry , organic chemistry
Activated Quinones: Regiospecific Syntheses of Substituted Dibenzo [ b , d ]pyran‐6‐ones and Benzo[ b ]naphtho [ d ]pyran‐6‐ones The reaction of 2‐methoxycarbonyl‐1, 4‐benzoquinone (1) with substituted phenols leads in an acid‐catalyzed, regiospecific way to substituted dibenzo [ b , d ]‐pyran‐6‐ones (compounds 3 and 6 ). The cycloaddition of 1,3‐butadiene to the latter yields compounds 7. Tautomerisation of 7 and oxidation gives the benzo[ b ]‐naphtho[ d ]pyran‐6‐ones 8 and 10 , respectively.