19026-83-6

Upstream product

• 768-95-6 1-adamanthanol 
• 79-06-1 2-propenamide 
• 768-90-1 1-Adamantyl bromide 
• 107-13-1 acrylonitrile 
• 768-94-5 1-Adamantanamine 
• 814-68-6 acryloyl chloride 
• 79-10-7 acrylic acid 

Downstream Products

• 1354707-97-3 6-(2-((1-adamantyl)carbamoyl)ethyl)-6-nitro-1,4-dibenzylperhydro-1,4-diazepine 

Relevant academic research and scientific papers

Switchable hydrogels obtained by supramolecular cross-linking of adamantyl-containing LCST copolymers with cyclodextrin dimers

En route to intelligent hydrogels: Copolymers of N-isopropylacrylamide containing adamantyl groups can be cross-linked noncovalently with cyclodextrin dimers. This results in thermosensitive hydrogels with cloud points that are lower than those of the pure copolymers. Addition of monomeric methylated cyclodextrin results in an increase in the cloud points but has no significant influence on the viscosity of the copolymer solution. (Figure Presented)

Ritter reaction of organic nitriles with 1-bromo- and 1-hydroxyadamantanes catalyzed by manganese compounds and complexes

Manganese compounds and complexes [MnCl2, MnBr2, Mn(OAc)2, Mn(acac)2, Mn(acac)3, Mn 2(CO)10] catalyze Ritter reaction of organic nitriles with 1-bromo- and 1-hydroxyadamantanes. The reaction proceeds in water environment in the absence of acids at 100-130°C over 3-5 h and affords N-(adamantan-1-yl)amides in 75-100% yields.

Clickable coupling of carboxylic acids and amines at room temperature mediated by SO2F2: A significant breakthrough for the construction of amides and peptide linkages

The construction of amide bonds and peptide linkages is one of the most fundamental transformations in all life processes and organic synthesis. The synthesis of structurally ubiquitous amide motifs is essential in the assembly of numerous important molecules such as peptides, proteins, alkaloids, pharmaceutical agents, polymers, ligands and agrochemicals. A method of SO2F2-mediated direct clickable coupling of carboxylic acids with amines was developed for the synthesis of a broad scope of amides in a simple, mild, highly efficient, robust and practical manner (>110 examples, >90% yields in most cases). The direct click reactions of acids and amines on a gram scale are also demonstrated using an extremely easy work-up and purification process of washing with 1 M aqueous HCl to provide the desired amides in greater than 99% purity and excellent yields.

Synthesis of N-(Adamantan-1-yl)carbamides by Ritter Reaction from Adamantan-1-ol and Nitriles in the Presence of Cu-Catalysts

A selective synthesis of (Z)-N-(adamantan-1-yl)carbamides by the reaction of adamantan-1-ol and nitriles in the presence of Cu catalysts was carried out. Z-Conformation of amides is established basing on X-ray diffraction analysis and 2D NMR data.

Tunable white-light emission by supramolecular self-sorting in highly swollen hydrogels

Fluorescence-tunable hydrogels especially emitting white-light were achieved by swelling hydrogels in solutions containing two kinds of dyes. The fluorescence of the dyes was enhanced by the orthogonal supramolecular complexation with different binding si

Indium-Triflate-Catalyzed Ritter Reaction in Liquid Sulfur Dioxide

The use of liquid sulfur dioxide as a reaction solvent facilitates the Ritter reaction between alcohols and nitriles. In(OTf)3 was found to be a viable catalyst for this transformation. The newly developed catalytic conditions for the Ritter reaction were successfully applied to the synthesis of various amides, which were formed in good to excellent yields. The catalytic activation of secondary alcohols for Ritter reactions in liquid sulfur dioxide was also found to be effective.

Microwave assisted, Ca(II)-catalyzed Ritter reaction for the green synthesis of amides

An efficient solvent-free synthesis of amides by Ca(II) catalyzed Ritter reaction has been reported under microwave irradiation. This green protocol tolerates the substrate diversity and delivers the high yielding amides with minimal loading of inexpensive and more abundant Ca(II) catalyst.

Synthesis of 6-substituted 6-nitroperhydro-1,4-diazepines via novel tandem retro-Henry and Mannich/Michael reactions

N,N′-Dibenzyl-6-hydroxymethyl-6-nitroperhydro-1,4-diazepine was converted into a nitronate via retro-Henry reaction, followed by either Michael reaction with several acrylic derivatives or Mannich reaction with different amines, thus leading to 6-substitu

N-adamantylation of arylsulfonyl(sulfanyl)propionitriles

A method for the synthesis of new 1-aminoadamantane derivatives, the N-adamantylamides of arylsulfonyl(sulfanyl)propionic acids, is developed. It was shown that the reaction of arylsulfonyl(sulfanyl)propionitriles with 1-hydroxyadamantane under the classi

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.