26482-50-8

Upstream product

• 281-23-2 adamantane 
• 149552-43-2 [N-(nosyl)imino]phenyliodinane 
• 935-56-8 1-chloroadamantane 
• 768-93-4 1-iodoadamantane 
• 768-90-1 1-Adamantyl bromide 
• 6325-93-5 p-nitrobenzenesulfonamide 
• 768-94-5 1-Adamantanamine 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 

Relevant academic research and scientific papers

Intermolecular Radical C(sp3)?H Amination under Iodine Catalysis

The direct amination of aliphatic C?H bonds has remained one of the most tantalizing transformations in organic chemistry. Herein, we report on a unique catalyst system, which enables the elusive intermolecular C(sp3)?H amination. This practical synthetic strategy provides access to aminated building blocks and fosters innovative multiple C?H amination within a new approach to aminated heterocycles. The synthetic utility is demonstrated by the synthesis of four relevant pharmaceuticals.

Structural and energetic aspects of adamantane and memantine derivatives of sulfonamide molecular crystals: Experimental and theoretical characterisation

A number of new sulfonamide compounds with adamantane and memantine fragments were synthesised and characterised. Their single crystals were grown and crystal structures were determined. XPac analysis has revealed three sets of isostructural crystals based on adamantane/memantine-specific hydrogen bond patterns. The use of QTAIMC and Hirshfeld surface analysis allowed elucidating the influence of functional groups and molecular arrangement on the strength of inter- and intramolecular non-covalent interactions in crystals and overall packing efficiency. It was found that the bulky memantine fragment hinders the formation of C(4) hydrogen-bonded chains, leading to the formation of dimeric structures with lower stabilisation energy. The layered packing of hydrophobic fragments in the group of isostructural crystals was found to be the most effective for a group of adamantane derivatives of P21/c symmetry.

Sulfonamide-Linked ciprofloxacin, sulfadiazine and amantadine derivatives as a novel class of inhibitors of jack bean urease; synthesis, kinetic mechanism and molecular docking

Sulfonamide derivatives serve as an important building blocks in the drug design discovery and development (4D) process. Ciprofloxacin-, sulfadiazine- and amantadine-based sulfonamides were synthesized as potent inhibitors of jack bean urease and free rad

Visible-light-mediated, nitrogen-centered radical amination of tertiary alkyl halides under metal-free conditions to form α-tertiary amines

A mild and operationally convenient amino-functionalization of a range of tertiary alkyl halides by reaction with iminoiodinanes (PhINNs) and I2 has been developed. According to the mechanistic experiments described within, the reaction is spec

Nonheme iron-mediated amination of C(sp3)-H bonds. Quinquepyridine-supported iron-imide/nitrene intermediates by experimental studies and DFT calculations

The 7-coordinate complex [Fe(qpy)(MeCN)2](ClO4) 2 (1, qpy = 2,2′:6′,2″:6″, 2′′′:6′′′,2′′′′- quinquepyridine) is a highly active nonheme iron catalyst for intra- and intermolecular amination of C(sp3)-H bonds. This complex effectively catalyzes the amination of limiting amounts of not only benzylic and allylic C(sp3)-H bonds of hydrocarbons but also the C(sp3)-H bonds of cyclic alkanes and cycloalkane/linear alkane moieties in sulfamate esters, such as those derived from menthane and steroids cholane and androstane, using PhI=NR or "PhI(OAc)2 + H2NR" [R = Ts (p-toluenesulfonyl), Ns (p-nitrobenzenesulfonyl)] as nitrogen source, with the amination products isolated in up to 93% yield. Iron imide/nitrene intermediates [Fe(qpy)(NR)(X)]n+ (CX, X = NR, solvent, or anion) are proposed in these amination reactions on the basis of experimental studies including ESI-MS analysis, crossover experiments, Hammett plots, and correlation with C-H bond dissociation energies and with support by DFT calculations. Species consistent with the formulations of [Fe(qpy)(NTs)2] 2+ (CNTs) and [Fe(qpy)(NTs)]2+ (C) were detected by high-resolution ESI-MS analysis of the reaction mixture of 1 with PhI=NTs (4 equiv). DFT calculations revealed that the reaction barriers for H-atom abstraction of cyclohexane by the ground state of 7-coordinate C NTs and ground state of C are 15.3 and 14.2 kcal/mol, respectively, in line with the observed high activity of 1 in catalyzing the C-H amination of alkanes under mild conditions.

Iodine-catalyzed aminosulfonation of hydrocarbons by imidoiodinanes. a synthetic and mechanistic investigation

The amino-functionalization of a range of benzylic and some aliphatic saturated and unsaturated hydrocarbons by reaction with imido-iodinanes (PhI=NSO2Ar) is catalyzed by I2 under operationally simple and mild conditions. The first examples of 1,2-functionalization of unactivated C-H bonds using imido-iodinanes as aminating agents are reported. Mechanistic investigations, including Hammett analysis, kinetic isotope effects, a cyclopropane clock experiment, and stereoselectivity tests, are indicative of a stepwise pathway in C-N bond formation. Investigation into the nature of the active aminating species has led to the isolation of a novel aminating agent formulated as (ArSO2N)xIy (x = 1, y = 2; or x = 3, y = 4).

Rhodium(II)-Catalyzed CH Insertions with imino>phenyl-λ3-iodane

The catalyzed decomposition of imino>phenyl-λ3-iodane (NsN=IPh) resulted in formal insertions into CH bonds, activated by phenyl or vinyl groups, or by O-substituents.Scope and limitations of the reaction were investigated.Yields of up to 84percent were achieved in the most favorable cases.Yields were enhanced by electron-releasing substituents and decreased by steric hindrance.Aziridination competed with allylic insertion with olefinic substrates.The insertion reaction proceeded with retention of configuration.With chiral RhII catalysts, a modest asymmetric induction was observed.A mechanism involving direct insertion by a Rh-complexed nitrene into the CH bond is proposed.

Rhodium(II)-catalyzed aziridinations and ch insertions with [N-(p-nitrobenzenesulfonyl)imino]phenyliodinane

The [Rh2(OAc)4]-catalyzed decomposition of NsN=IPh {[N-(p-nitrobenzenesulfonyl)imino]phenyliodinane} in the presence of olefins affords aziridines in yields of up to 85%. The aziridination of cis-hex-2-ene and cis-β-methylstyrene is stereospecific, but, cis-stilbene affords a 3:1 mixture of cis- and trans-aziridines in low yield. With chiral Rh(II) catalysts, optically active aziridines are formed having enantiomeric excesses of up to 73%. The NsN-IPh-[Rh2(OAc)4] system is also efficient for the allylic amination of olefins and for insertion into CH bonds, activated by phenyl or oxygen substituents.