Azonia polycyclic quinones,  o ‐diazo‐oxides and related products | Zendy

Fields D. L. | Zendy; Miller J. B. | Zendy

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Azonia polycyclic quinones, o ‐diazo‐oxides and related products

Author(s) -

Fields D. L.,

Miller J. B.

Publication year - 1970

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.5570070113

Subject(s) - chemistry , diazo , electrophile , anthracene , hydrogen chloride , methanol , nitric acid , chloride , medicinal chemistry , organic chemistry , catalysis

4α‐Azoniaanthracene‐5,6‐ and 5,8‐dione salts have been prepared by nitric acid oxidation of their respective diols, and are shown to function as either an electrophilic dienophile or a diene component in Diels‐Alder‐type reactions. Several azonia o ‐quinones have been treated with tosylhydrazine in methanol saturated with hydrogen chloride to give unusually stable o ‐diazo‐oxides. A four‐step dehydroxylation procedure is detailed for the conversion of .5,6‐dihydroxy‐4α‐azonia‐anthracene salts to new 5‐hydroxy‐4α‐azoniaanthracene salts.

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