Regioselective and Stereoselective Synthesis of Pyridine-Fused Benzoxepine Derivatives by Intramolecular Reductive Heck Cyclization

An efficient method for the synthesis of 6,11‐dihydro[2]benzoxepino[4,3‐b]pyridine derivatives via Pd(0) catalyzed intramolecular reductive Heck cyclization is reported. The method offers the regioselective and stereoselective synthesis of highly functionalized pyridine‐fused benzoxepine derivatives...

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Bibliographic Details
Published in:Journal of heterocyclic chemistry 2016-01, Vol.53 (1), p.80-88
Main Authors: Mondal, Shovan, Debnath, Sudarshan
Format: Article
Language:English
Subjects:
Diffraction
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Summary:An efficient method for the synthesis of 6,11‐dihydro[2]benzoxepino[4,3‐b]pyridine derivatives via Pd(0) catalyzed intramolecular reductive Heck cyclization is reported. The method offers the regioselective and stereoselective synthesis of highly functionalized pyridine‐fused benzoxepine derivatives in 75–85% yields under mild conditions. Chemoselective Sonogashira coupling is utilized for the synthesis of cyclization precursors. The stereochemistry of the exocyclic double bond of 6,11‐dihydro[2]benzoxepino[4,3‐b]pyridine derivatives is confirmed from single crystal X‐ray diffraction. The absence of N–Pd(II) interaction results in a reverse stereochemistry of the exocyclic double bond of dibenzoxepine derivative.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.2357