111574-87-9

Upstream product

• 71-44-3 Spermine 
• 19264-68-7 9-benzoyl-9H-carbazole 
• 100-52-7 benzaldehyde 
• 532-28-5 (RS)-mandelonitrile 
• 613-90-1 benzoyl cyanide 

Relevant academic research and scientific papers

N-acylcarbazole as a selective transamidation reagent

N-acylation reaction offers an opportunity to develop an efficient synthesis of amide group-containing molecules. We found that N-acyl carbazoles showed remarkable selectivity in transamidation. Sterically less hindered primary amines are selectively acylated with N-acyl carbazoles without any additives. Various functional groups such as alcohol, phenol, indole, and aniline moieties are tolerated under mild conditions. The synthetic utility was displayed in one-pot synthesis of an N-acyl polyamine natural product. The terminal amines of spermidine were selectively benzoylated with N-benzoyl carbazole, followed by acetylation reaction accomplished the total synthesis in a highly efficient manner.

Ruthenium-Catalyzed Oxidations of Alcohols

A combination of low-valent ruthenium complexes and peroxides such as t-BuOOH and peracids serves as efficient catalytic systems for the oxidation of aromatic and aliphatic hydroxy compounds. The utility of these methods was demonstrated by the synthesis of acyl cyanides which are versatile synthetic intermediates. The principle of the catalytic oxidations with peracids lead to the novel and efficient method for aerobic oxidation of alcohols in the presence of aldehydes. This reaction is of importance in synthetic and large scale industrial processes and from environmental points of view. The present principle will provide new chemistry of oxidative transformations of various industrially important functional materials.

Ruthenium-catalyzed oxidations for selective syntheses of ketones and acyl cyanides. Selective acylation of amino compounds with acyl cyanides

Oxidation of alcohols to the corresponding carbonyl compounds with tert-butyl hydroperoxide in the presence of dichlorotris(triphenylphosphine)ruthenium catalyst gives the corresponding carbonyl compounds with high efficiency. This method can be applied to the oxidation of cyanohydrins to give acyl cyanides which are versatile synthetic intermediates. Acylation of amino compounds with acyl cyanides thus obtained proceeds chemoselectively. Thus, the reaction of amino alcohols with acyl cynides gives N-acylated products exclusively. In the similar N-acylation of polyamines primary amines are selectively acylated in the presence of secondary amines. These reactions are highly useful for the synthesis of spermidine and spermine alkaloids such as spermidine alkaloids such as spermidine siderophores. Dimeric cyclocoupling reaction of diacyl cyanides such as iso- and terephthaloyl cyanides with polyamines can be performed under the similar reaction conditions to give the corresponding polyazamacrocycles with high efficiency.

Chemoselective Acylation of Primary Amines in the Presence of Secondary Amines with Acyl Cyanides. Highly Efficient Methods for the Synthesis of Spermidine and Spermine Alkaloid

Acyl cyanides are highly useful reagents for the chemoselective acylation of primary amines in the presence of secondary amines.The reaction provides the versatile method for the shortstep synthesis of various naturally occurring polyamines.