Green and efficient synthesis of 5-amino-1H-pyrazole-5-carbonitriles utilizing novel modified LDH
Sarieh Momeni1, Ramin Ghorbani-Vaghei1
1Department of Organic Chemistry, Faculty of Chemistry and Petroleum Sciences, Bu-Ali Sina University Hamedan Iran rgvaghei@yahoo.com ghorbani@basu.ac.ir.
Abstract:
This research introduced a novel nano catalyst, LDH@PTRMS@DCMBA@CuI, developed from nano copper immobilized on a layered double hydroxide modified with a new type of sulfonamide: N 1,N 3-dicarbamimidoylbenzene-1,3-disulfonamide (DCMBA). This catalyst demonstrated significant activity and selectivity in synthesizing 5-amino-1H-pyrazole-5-carbonitrile derivatives. The derivatives were produced via a three-component one-pot reaction combining benzaldehydes, malononitrile, and phenyl hydrazine in H2O/EtOH solvent at 55 °C. This innovative synthesis strategy offered several advantages, including eco-friendliness, simplicity, stability, mild reaction conditions, easy purification of products, short reaction times (15-27 min), and excellent yields (85-93%). Additionally, the green methodology was validated by the catalyst's reusability over four consecutive cycles without significant loss of catalytic activity.
Related Concept Videos
Preparation of 1° Amines: Azide Synthesis
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Preparation of 1° Amines: Gabriel Synthesis
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Nitriles to Amines: LiAlH4 Reduction
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
Preparation of Aldehydes and Ketones from Nitriles and Carboxylic Acids
Reducing carboxylic acid derivatives like acyl chlorides (RCOCl), esters (RCO2R′), and nitriles (RCN) using milder aluminum hydride agents like lithium tri-tert-butoxyaluminum hydride [LiAlH(O-t-Bu)3] and diisobutylaluminum hydride [DIBAL-H]...
Preparation of Nitriles
Preparation of Amines: Reduction of Amides and Nitriles
Amides can be reduced to primary, secondary, and tertiary amines using catalytic hydrogenation, active metals like Fe,...


