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New polycyclic pyran ring systems
Author(s) -
Mazzei Mauro,
Roma Giorgio,
Ermili Aldo
Publication year - 1978
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570150416
Subject(s) - chemistry , pyran , acetic acid , formaldehyde , ring (chemistry) , cleavage (geology) , acetic anhydride , benzopyran , medicinal chemistry , stereochemistry , organic chemistry , catalysis , geotechnical engineering , fracture (geology) , engineering
Reaction of 1‐oxo‐3‐dialkylamino‐1 H ‐naphtho[2,1‐ b ]pyrans, 4‐hydroxycoumarin and formaldehyde gave rise to the formation of 1‐oxo‐2‐((2‐oxo‐4′‐hydroxy‐2′ H ‐1′‐benzopyran‐3′‐yl)‐melhyl J‐3‐dialkylamino‐1 H ‐naphtho[2,1‐ b ]pyrans. When these compounds were refluxed in glacial acetic acid, cyclization occurred and 6,8‐dioxo‐6 H ,7 H ,07‐,5,15,16‐trioxadibenzo[ a,j ]‐naphthacene arose by cleavage of the dialkylamino group. In a similar manner, starting from suitable products, many other trioxanaphthacene or azadioxanaphthacene derivatives were synthesized.