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One‐pot synthesis of novel ( E )‐3‐(3, 8a‐dihydro‐2 H ‐oxazolo[3,2‐a]pyridin‐2‐ylidene)chroman‐2‐one derivatives
Author(s) -
Olyaei Abolfazl,
Feizy Elaheh,
Aghajanzadeh Atiye
Publication year - 2021
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.4212
Subject(s) - chemistry , triethylamine , pyridinium , acetonitrile , tandem , pyridine , bromide , intramolecular force , medicinal chemistry , combinatorial chemistry , stereochemistry , organic chemistry , materials science , composite material
An efficient synthetic procedure for the preparation of novel ( E )‐3‐(3,8a‐dihydro‐2 H ‐oxazolo[3,2‐a]pyridin‐2‐ylidene)chroman‐2‐one derivatives was developed. A sequential one‐pot, two‐step tandem reaction starting from 3‐(2‐bromoacetyl)‐2 H ‐chromen‐2‐one derivatives synthesized, pyridine, and naphthols in the presence of triethylamine proceeded smoothly in acetonitrile under reflux conditions. In this process, 2‐oxo‐2 H ‐chromen‐3‐yl)ethyl)pyridinium bromide derivatives as intermediate produced in situ , followed by Michael addition of naphthoxide anion and intramolecular cylization, resulted the corresponding products in good to high yields. All of the compounds were obtained in high purity without any use of more purification.