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Reaction of sulfene with heterocyclic N,N ‐disubstituted α‐aminomethyleneketones. VIII. Synthesis of furo[2,3‐ h ]‐1,2‐benzoxathiin derivatives
Author(s) -
Mosti Luisa,
Sche Pietro,
Menozzi Giulia,
Romussi Giovanni,
Baccichetti Francarosa
Publication year - 1982
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.5570190550
Subject(s) - chemistry , furan , yield (engineering) , dehydrogenation , cycloaddition , medicinal chemistry , stereochemistry , organic chemistry , catalysis , materials science , metallurgy
Cycloaddition of sulfene to N,N ‐disubstituted ( E )5‐aminomethylene‐6,7‐dihydrobenzo[ b ]furan‐4(5 H )ones I gave, only in the case of aliphatic N ‐substitution and generally in satisfactory yields, N,N ‐disubstituted 4‐amino‐3,4,5,6‐tetrahydrofuro[2,3‐ h ]‐1,2‐benzoxathiin 2,2‐dioxides II, which are derivatives of the new heterocyclic system furo[2,3‐ h ]‐1,2‐benzoxathiin. The 4‐dimethylamino and 4‐piperidino cycloadducts IIa,e were dehydrogenated with DDQ to the corresponding 4‐dialkylamino‐3,4‐dihydrofuro[2,3‐ h ]‐1,2‐benzoxathiin 2,2‐dioxides IIIa,e in low yield. Compounds IIIa,e were tested for photobiological activity and found to be inactive.