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Mild, Stereoselective, and Highly Efficient Synthesis of N ‐Acylhydrazones Mediated by CeCl 3 ·7H 2 O in a Broad Range of Solvents (Eur. J. Org. Chem. 29/2014)
Author(s) -
dos Santos Filho José Maurício
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201490081
Subject(s) - chemistry , stereoselectivity , oxime , stereochemistry , reaction conditions , organic chemistry , combinatorial chemistry , catalysis
The cover picture shows in the central core the general reaction between arylhydrazides and aldehydes or ketones, catalysed by CeCl 3 · 7H 2 O, leading to some significant examples of N ‐acylhydrazones. The depicted examples exhibit a very broad structural diversity, focusing on their structural particularities. Sensitive substrates like sugars, oxime‐ or ferrocenyl‐bearing aldehydes can easily be converted into the corresponding products without any signs of decomposition. Also, bulky aldehydes or ketones undergo this reaction without problems, leading to significant advances in the synthesis of this compound class; an example is the first direct synthesis of camphor‐ N ‐acylhydrazone. Due to the mild reaction conditions, only E ‐isomers were identified, evidencing the importance of the method for synthetic chemistry. The figures around the molecular structures represent some of the common biological activities associated with the N ‐acylhydrazones, which are largely explored in the field of medicinal chemistry. Details are discussed in the article by J. M. dos Santos Filho on p. 6411 ff .