Synthesis of azafluorenone via oxidative intramolecular Heck cyclization

A very short and highly efficient protocol to azafluorenone exploiting intramolecular oxidative Heck cyclization using Pd(0) is presented. Precursor alcohols afforded azafluorenone in a single step with simultaneous oxidation and cyclization under Heck reaction condition in excellent yield. This met...

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Bibliographic Details
Published in:Tetrahedron letters 2013-01, Vol.54 (1), p.63-65
Main Authors: Dhara, Shubhendu, Ahmed, Atiur, Nandi, Sukla, Baitalik, Shantanu, Ray, Jayanta K.
Format: Article
Language:English
Subjects:
2-Bromoprydine-3-carboxaldehyde
Alcohols
Alkaloids
Azafluorenone
Grignard reaction
Intramolecular Heck reaction
Methodology
Oxidation
Precursors
Synthesis (chemistry)
Tetrahedrons
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Summary:A very short and highly efficient protocol to azafluorenone exploiting intramolecular oxidative Heck cyclization using Pd(0) is presented. Precursor alcohols afforded azafluorenone in a single step with simultaneous oxidation and cyclization under Heck reaction condition in excellent yield. This methodology could be very much crucial in the total synthesis of azafluorenone alkaloids for promising pharmacological activity.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2012.10.085