24813-21-6

Usage

InChI:InChI=1/C16H20N2O/c19-15(14-2-1-3-17-10-14)18-16-7-11-4-12(8-16)6-13(5-11)9-16/h1-3,10-13H,4-9H2,(H,18,19)

Upstream product

• 10400-19-8 3-pyridinecarbonyl chloride 
• 768-94-5 1-Adamantanamine 
• 768-95-6 1-adamanthanol 
• 1493-25-0 3-pyridinecarbonyl fluoride 
• 59-67-6 nicotinic acid 
• 100-54-9 pyridine-3-carbonitrile 
• 768-90-1 1-Adamantyl bromide 
• 98-92-0 nicotinamide 

Relevant academic research and scientific papers

Direct Access to Acyl Fluorides from Carboxylic Acids Using a Phosphine/Fluoride Deoxyfluorination Reagent System

A fast and simple method for deoxyfluorination of carboxylic acids is presented. The protocol employs commodity chemicals (PPh3, NBS, fluoride), affording products in excellent yields under mild conditions. Acyloxyphosphonium ion, the key reaction intermediate, was identified by NMR spectroscopic methods. Br?nsted acidic conditions are essential for efficient C-F bond formation. The protocol displays scalability, high functional group tolerance, chemoselectivity, and easy purification of products. Deoxyfluorination of active pharmaceutical ingredients was established.

Cavitand-porphyrins

The synthesis and characterization of new nanoscale container molecules 7 and 8 are described. They are covalent hybrids of deepened, self-folding cavitands and metalloporphyrins. In receptor 7, the Zn-porphyrin wall is directly built onto the cavitand skeleton. Host 8 features a large unimolecular cavity containing two cavitands attached with the Zn-porphyrin wall. Its dimensions, ～10 × 25 A, place it among the largest synthetic hosts prepared to date. A series of adamantyl- and pyridyl-containing guests 14-20 of various lengths were prepared and used to determine the hosts' binding abilities in solution using UV/vis and 1H NMR spectroscopy. Intramolecular hydrogen bonds at the upper rims of the cavitands resist the unfolding of the inner cavities and thereby increase the energetic barrier to guest exchange. The exchange is slow on the NMR time scale (at ≤300 K), and kinetically stable complexes result. When the cavities and metalloporphyrins participate simultaneously in the binding event, very high affinities for guests are found (-ΔG295 up to 10 kcal mol-1 in toluene), to which the porphyrin fragments contribute significantly (-ΔG295 up to 6 kcal mol-1). The pairwise selection of two different guests by molecular container 8 is reported, and the termolecular complex formed raises the possibility of metal-catalyzed bimolecular reactions in these containers.

Adamantylation and adamantylalkylation of amides, nitriles, and ureas in trifluoroacetic acid

A new preparative procedure was developed for N-adamantylation of carboxylic acids amides and ureas, and C5-adamantylation of barbituric acid in trifluoroacetic acid medium with tertiary adamantanols and 1-adamantylalkanols. The reaction of 2-adamantanols and secondary 1-adamantylalkanols with nitriles was for the first time used in the preparation of W-(2-adamantyl)-and N-(1-adamantylalkyl)amides.

Adamantylation and adamantylalkylation of amides, nitriles and ureas in trifluoroacetic acid

A new preparative method for N-adamantylation of carboxylic acid amides, ureas and for C5-adamantylation of barbituric acid in trifluoroacetic acid (TFA) is proposed. Tertiary 1-adamantanols and 1-(1-adamantyl)alkanols were used as adamantylating agents. The reaction of 1-(1-adamantyl)alkanols with nitriles in TFA solution was employed for the first time for the preparation of N-[1-(1-adamantyl)alkyl]amides.

DERIVATIVES OF ADAMANTANE. II. USE OF TRIFLUOROACETIC ACID IN THE RITTER REACTION

For the case of 1-substituted adamantanes it was possible to realize the synthesis of amides by the Ritter reaction with high yields using trifluoroacetic acid as catalyst and solvent.This makes it possible to realize the process in a homogenous phase and to remove the excess of the nitrile and the excess of the acid itself from the reaction mass by hydrolysis of the intermediate immonium comples.On account of the mild conditions labile nitriles and aminonitriles, in particular, can be used in the reaction.