Reaction of pyromeconic acid with β‐diazopropionic ester. Synthesis and attempted cyclization of β‐(4 H ‐pyran‐4‐on‐3‐yloxy)propionic acid | Zendy

Looker James H. | Zendy; Brannigan Lawrence H. | Zendy; Prokop Robert J. | Zendy

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Reaction of pyromeconic acid with β‐diazopropionic ester. Synthesis and attempted cyclization of β‐(4 H ‐pyran‐4‐on‐3‐yloxy)propionic acid

Author(s) -

Looker James H.,

Brannigan Lawrence H.,

Prokop Robert J.

Publication year - 1975

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.5570120320

Subject(s) - chemistry , decarboxylation , pyran , alkylation , hydrolysis , benzoic acid , propionate , organic chemistry , ring (chemistry) , medicinal chemistry , catalysis

A procedure which utilizes a special sublimate condenser for preparation of pyromeconic acid (I) by decarboxylation of either meconic or comenic acid is reported. O ‐Alkylation of pyromeconic acid with ethyl β‐diazopropionate ex situ yields ethyl β‐(4 H ‐pyran‐4‐on‐3‐yloxy)‐propionate (II), acidic hydrolysis of which affords the free acid III. The acid III is refractory to ring‐closure to a chromanone analog IV under a wide range of acidic conditions. O ‐Allylation of 1 gives 3‐allyloxy‐4 H ‐pyran‐4‐one (V) as a low‐melting crystalline solid.

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