904816-62-2

Usage

InChI:InChI=1/C12H20N2O2/c1-11(2,3)16-10(15)14-12(9-13)7-5-4-6-8-12/h4-8H2,1-3H3,(H,14,15)

Upstream product

• 22821-76-7 4-(methylsulfonyl)benzonitrile 
• 115951-16-1 1-tert-butoxycarbonylaminocyclohexanecarboxylic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 108-94-1 cyclohexanone 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 3712-40-1 tert-butyl cyclohexylcarbamate 

Relevant academic research and scientific papers

Decarboxylative Cyanation of Aliphatic Carboxylic Acids via Visible-Light Flavin Photocatalysis

An operationally simple method is disclosed for the decarboxylative cyanation of aliphatic carboxylic acids at room temperature. Riboflavin tetraacetate, which is an inexpensive organic photocatalyst, promotes the oxidation of carboxylic acids upon visible-light activation. After decarboxylation, the generated radicals are trapped by TsCN, yielding the desired nitriles without any further additive, in a redox-neutral process. Importantly, this protocol can be adapted to flow conditions.

Photoreactive fused aziridinylpiperazines on the background of 4-substituted chalcones and their benzimidazolic analogs

The reaction of bromo-substituted chalcones with various diamino-compounds leads to the fused heterocyclic products, aziridinylpiperazines, exhibiting photoreactivity in the crystalline state. Crystals of 4-nitrosubstituted compounds of this family change their color from yellowish to deep violet-blue, 4-cyanosubstituted ones – from yellowish to pink at UV irradiation. Discussion on the mechanism of this phototransformation is still in progress, however, several facts points to the free radial nature of the photogenerated colored semi-products stabilized only by crystalline state of the irradiated samples. Formation of a mixture of positional isomers at interaction of bromo-chalcones with asymmetric diamines of aliphatic/alicyclic or aromatic series at synthesis of the title compounds is of significant interest as well.

Photoinduced direct cyanation of C(sp3)-H bonds

A general and practical synthetic protocol for the direct transformation of unreactive C(sp3)-H bonds to C(sp3)-CN bonds has been developed. The homolytic cleavage of the C-H bond is initiated by photo-excited benzophenone, and the resulting carbon radical subsequently reacts with tosyl cyanide to afford the corresponding nitrile in a highly efficient manner. The present methodology is widely applicable to various starting materials including ethers, alcohols, amine derivatives, alkanes, and alkylbenzenes. This newly developed C-H cyanation protocol provides a powerful tool for selective one-carbon elongation for the construction of architecturally complex molecules. Georg Thieme Verlag Stuttgart - New York.