Regioselective and Stereoselective Synthesis of Pyridine‐Fused Benzoxepine Derivatives by Intramolecular Reductive Heck Cyclization[1]. (8th January 2015)

• Record Type: Journal Article
• Authors: Mondal, Shovan; Debnath, Sudarshan
• Is Part Of: Journal of heterocyclic chemistry. Volume 53:Number 1(2016:Jan.)
• Page Start: 80
• Page End: 88
• Publication Date: 2015-01-08
• Subjects: Heterocyclic compounds -- Periodicals; 547.59
• DOI: 10.1002/jhet.2357
• Languages: English
• ISSNs: 0022-152X

Abstract

Abstract : An efficient method for the synthesis of 6, 11‐dihydro[2]benzoxepino[4, 3‐ b ]pyridine derivatives via Pd(0) catalyzedintramolecular reductive Heckcyclization is reported. The method offers theregioselective andstereoselective synthesis of highly functionalized pyridine‐fused benzoxepine derivatives in 75–85% yields under mild conditions. ChemoselectiveSonogashira coupling is utilized for the synthesis ofcyclization 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. Abstract :