Chalcones as Versatile Synthons for the Synthesis of 5- and 6-membered Nitrogen Heterocycles

Author(s): Helio M.T. Albuquerque, Clementina M.M. Santos, Jose A.S. Cavaleiro, Artur M.S. Silva

Journal Name: Current Organic Chemistry

Volume 18 , Issue 21 , 2014

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Abstract:

Chalcones belong to the flavonoid family which constitutes one of the major classes of naturally occurring oxygen heterocyclic compounds. The α,β-unsaturated carbonyl system of chalcones possesses two electrophilic reactive centers allowing them to participate in addition reactions via attack to the carbonyl group (1,2-addition) or involving the β-carbon (1,4-conjugate addition), leading to the synthesis of promising bioactive heterocyclic compounds. The purpose of this review is to present a systematic survey of the most recent literature that uses chalcones in the synthesis of biologically active 5- and 6-membered nitrogen heterocycles such as pyrroles, indoles, isoxazoles, imidazoles, pyrazoles, indazoles, triazoles, tetrazoles, pyridines and pyrimidines. Efficiency, easy-to-handle and cheap reagents, alternative heating conditions and greener protocols will be highlighted. In this review we will cover the literature since the beginning of the 21st century in more than 400 publications.

Keywords: Chalcones, cycloaddition reactions, Michael addition, nitrogen heterocyclic compounds, reactivity, synthetic methods.

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Article Details

VOLUME: 18
ISSUE: 21
Year: 2014
Page: [2750 - 2775]
Pages: 26
DOI: 10.2174/1385272819666141013224253
Price: $58

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