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HERO ID
4280275
Reference Type
Journal Article
Title
Chalcones as Versatile Synthons for the Synthesis of 5-and 6-membered Nitrogen Heterocycles
Author(s)
Albuquerque, HMT; Santos, CMM; Cavaleiro, JAS; Silva, AMS
Year
2014
Is Peer Reviewed?
Yes
Journal
Current Organic Chemistry
ISSN:
1385-2728
EISSN:
1875-5348
Volume
18
Issue
21
Page Numbers
2750-2775
DOI
10.2174/1385272819666141013224253
Web of Science Id
WOS:000345433000004
Abstract
Chalcones belong to the flavonoid family which constitutes one of the major classes of naturally occurring oxygen heterocyclic compounds. The alpha,beta-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 beta-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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