N‐Acylhydrazones as Versatile Electrophiles for the Synthesis of Nitrogen‐Containing Compounds

Abstract

The use of N-acylhydrazones as electrophiles in reactions with nucleophiles has recently made some important advances. N-Acylhydrazones, which can be readily prepared and stored, act as stable imine surrogates in these reactions. The hydrazide products are useful, often chiral building blocks which can be transformed into various nitrogen-containing compounds by cleavage of the N--N bond. The N-acyl groups often play important roles as templates for metal catalysis in controlling stereochemistry. This Minireview summarizes the most recent results of N-acylhydrazone chemistry, and provides an overview of current developments in this field.

Synthesis of homoallylic amines and acylhydrazides by tin powder‐promoted multicomponent one‐pot allylation reactions

“…[70] Some of their reactions can even proceed smoothly in water. [71,72] Thus, we aimed to determine if the amines in the above reaction could be replaced by N-acylhydrazines to afford the corresponding N′-homoallylic hydrazides.…”

Uncatalyzed Three‐Component Synthesis of α‐Hydrazido Phosphonates

“…In addition, many imines are hygroscopic and are not sufficiently stable to be isolated, particularly, those derived from aliphatic aldehydes. N-Acylhydrazones have been broadly used as imine surrogates, [13] since they are versatile electrophiles, more stable than imines, and are capable of reacting with a great number of nucleophiles towards the synthesis of nitrogen-containing compounds. In spite of its interest, to the best of our knowledge, the hydrophosphonylation of N-acylhydrazones with dialkyl phosphites has been overlooked in the literature, [14] and only a few examples of the synthesis of α-hydrazino phosphonic acids have been reported.…”

Synthesis and testing of 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazole derivatives for antifungal activity against selected Candida Species

“…15 With this in mind, it was planned the synthesis of the 1,3,4-oxadiazoline target molecule from the versatile N-acylhydrazone substrate, using the strategy of closing the acyclic chain to give the 1,3,4-oxadiazoline core. The strategy is efficient to obtain the 1,3,4-oxadiazoline target molecule (Figure 1).…”