Tetraacetylethylene and nitrile oxides: Synthesis of spirofuranisoxazoles | Zendy

Adembri G. | Zendy; Di Tommaso A. | Zendy; Lampariello L. R. | Zendy; Scotton M. | Zendy

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Tetraacetylethylene and nitrile oxides: Synthesis of spirofuranisoxazoles

Author(s) -

Adembri G.,

Di Tommaso A.,

Lampariello L. R.,

Scotton M.

Publication year - 1988

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.5570250605

Subject(s) - nitrile , chemistry , tautomer , ring (chemistry) , aryl , medicinal chemistry , diacetyl , organic chemistry , alkyl

trans and cis ‐3‐Hexen‐2,5‐dione, 2 , reacted with nitrile oxides to give 4,5‐dihydroisoxazoles 3a‐c with the trans configuration. On the contrary the reaction between 3,4‐diacetyl‐3‐hexen‐2,5‐dione, 1 , with nitrile oxides yielded 3‐aryl‐8,9‐diacetyl‐7‐hydroxy‐7‐methyl‐1,6‐dioxa‐2‐azaspiro[4.4]nona‐3,8‐dienes 9a‐e. The reaction is completely regiospecific. The cycloadducts show ring‐open chain tautomerism.

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