Synthetic Methods and Reactions; 60¹. Improved One-Step Conversion of Aldehydes into Nitriles with Hydroxylamine in Formic Acid Solution

An Efficient and Improved Method for the Preparation of Nitriles from Primary Amides and Aldoximes†

“…However, many of these methods are deficient in some respect or other. Some are expensive, require vigorous reaction conditions, others involve hazardous [8] (selenium dioxide) and corrosive [9] (formic acid) reagents, the work-up is tedious or perhaps, more importantly, the method is not generally applicable to alkyl, aryl and heterocyclic compounds. Hence, there is considerable interest in finding convenient, less toxic, more affordable, universally applicable reagents with potential selectivity towards other protecting groups.…”

Efficient one-pot synthesis of cyanoferrocene from ferrocenecarboxaldehyde using NH2OH·HCl/KI/ZnO/CH3CN system

“…In addition, they can be converted to amines, ketones, carboxylic acids, esters and amides [8]. It should be noted that for the synthesis of nitriles, numerous methods are available [9,10], and new variants continue to appear. The most widely used general method is based on the dehydration of the corresponding aldoximes [10].…”

“…It should be noted that for the synthesis of nitriles, numerous methods are available [9,10], and new variants continue to appear. The most widely used general method is based on the dehydration of the corresponding aldoximes [10]. It is also well known that the cyano group itself is present in biologically important molecules including HIV protease inhibitors and 5-lipoxygerase inhibitors [11].…”

“…Therefore, the development of a general synthetic entry to cyanoferrocene would be great interest. Although numerous methods are known for preparation of nitriles [9,10], SciFinder search has revealed only few reports for the synthesis of cyanoferrocene [17][18][19]. Pauson research group tried several procedures to synthesize cyanoferrocene but the highest yield (78%) was obtained by the dehydration of the corresponding oximes with dicyclohexylcarbodiimide [17].…”

Solvent‐free Synthesis of Nitriles from Aldehydes Catalyzed by KF/Al2O3, Montmorillonite KSF and K10

“…10 Efficient one-pot methods were also developed using hydroxylamine hydrochloride and formic acid, 11 selenium dioxide, 12 pyridine in refluxing toluene, 13 or from nitroethane in the presence of sodium acetate buffer 14 or pyridine hydrochloride. 15 Das 16 has reported microwave assisted rapid conversion of aldehydes into nitriles using silica gel supported NaHSO 4 and NH 4 OAc catalysts.…”