A new regioselective synthesis of 2,3,4,5‐tetrahydro‐6 H ‐oxepino[3,2‐ c ]pyran‐6‐ones, and [1]benzopyran‐6‐ones | Zendy

Bravo Pierfrancesco | Zendy; Frigerio Massimo | Zendy; Ticozzi Calimero | Zendy

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A new regioselective synthesis of 2,3,4,5‐tetrahydro‐6 H ‐oxepino[3,2‐ c ]pyran‐6‐ones, and [1]benzopyran‐6‐ones

Author(s) -

Bravo Pierfrancesco,

Frigerio Massimo,

Ticozzi Calimero

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.5570250252

Subject(s) - chemistry , regioselectivity , benzopyran , pyran , intramolecular force , olefin fiber , toluene , dehydration , medicinal chemistry , organic chemistry , boiling , catalysis , biochemistry

Through an anti‐Markovnikow hydration of some olefin derivatives of 4‐hydroxy‐2‐pyrones, and 4‐hydroxy‐coumarins, followed by a regioselective intramolecular dehydration, involving the primary alcohols obtained and the enolic oxygen of the rings, promoted by Amberlyst 15 in boiling toluene, the new heterocycles 2,3,4,5‐tetrahydro‐6 H ‐oxepino[3,2‐ c ]pyran‐6‐one ( 3 ) and [1]benzopyran‐6‐ones ba,c were obtained in fair yields.

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