A convenient synthesis of 3‐aryl‐4 H ‐  Benzopyrano[3,4‐ d ]isoxazol‐4‐ones | Zendy

Litinas Konstantinos E. | Zendy; Nicolaides Demetrios N. | Zendy; Varella Evangelia A. | Zendy

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A convenient synthesis of 3‐aryl‐4 H ‐ Benzopyrano[3,4‐ d ]isoxazol‐4‐ones

Author(s) -

Litinas Konstantinos E.,

Nicolaides Demetrios N.,

Varella Evangelia A.

Publication year - 1990

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.5570270354

Subject(s) - chemistry , nitrile , regioselectivity , aryl , cycloaddition , pyridine , 1,3 dipolar cycloaddition , cleavage (geology) , medicinal chemistry , stereochemistry , organic chemistry , catalysis , alkyl , geotechnical engineering , fracture (geology) , engineering

Regioselective 1,3‐dipolar cycloaddition of nitrile oxides 5a‐c to ethyl o ‐hydroxycinnamate (3) gave the corresponding ethyl trans ‐3‐aryl‐4,5‐dihydro‐5‐(2‐hydroxyphenyl)‐4‐isoxazolecarboxylates 6a‐c . Their structure was confirmed by reductive cleavage to 1 and compounds 9a‐c . Compounds 6a‐c afforded upon heating in the presence of pyridine the 3‐aryl‐4 H ‐[1]benzopyrano[3,4‐ d ]isoxazol‐4‐ones 11a‐c . Compound 10c was also isolated from 6c and transformed thermally into 11c .

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