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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.