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Thermal Synthesis of 3‐Bromothieno[3,2‐ c ]pyridin‐4‐(5 H )‐one: A Telescoped Procedure with Tributylamine
Author(s) -
Boros Eric E.,
Kaldor Istvan
Publication year - 2015
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.1981
Subject(s) - chemistry , isomerization , isocyanate , thermal , pyridine , organic chemistry , medicinal chemistry , polymer chemistry , polyurethane , catalysis , thermodynamics , physics
3‐Bromothieno[3,2‐ c ]pyridine‐4‐(5 H )‐one ( 1 ) was prepared from (2 E )‐3‐(4‐bromo‐2‐thienyl)‐2‐propenoic acid ( 3 ) by the Eloy–Deryckere thermal benzo/heteropyridinone synthesis. A telescoped procedure was developed, which reduces some of the risk associated with the classic procedure. Use of tributylamine as an additive in this process was shown to facilitate E / Z ‐isomerization of the intermediate vinyl isocyanate and lower the temperature necessary for the overall thermal process.