56432-99-6

Upstream product

• 941-55-9 4-toluenesulfonyl azide 
• 281-23-2 adamantane 
• 935-56-8 1-chloroadamantane 
• 127-65-1 chloroamine-T 
• 768-95-6 1-adamanthanol 
• 70-55-3 toluene-4-sulfonamide 
• 24569-89-9 1,3-dehydroadamantane 
• 18522-92-4 sodium p-toluenesulfonamide 
• 55962-05-5 [N-(p-tolylsulfonyl)imino]phenyliodinane 
• 768-94-5 1-Adamantanamine 
• 98-59-9 p-toluenesulfonyl chloride 
• 1338062-05-7 4-methyl-N-[(2-propoxyphenyl)-λ³-iodanylidene]benzenesulfonamide 
• 75-05-8 acetonitrile 
• 100-47-0 benzonitrile 

Downstream Products

• 85858-29-3 1,3-bis(toluene-p-sulphonamido)adamantane 
• 935-56-8 1-chloroadamantane 
• 768-94-5 1-Adamantanamine 
• 1174638-32-4 C₂₅H₂₇NO₂S 

Relevant academic research and scientific papers

Organophotoredox-Catalyzed Decarboxylative N-Alkylation of Sulfonamides

We developed an organophotoredox-catalyzed reaction for N-alkylation of sulfonamides with aliphatic carboxylic acid-derived redox active esters as alkylating reagents. Under mild and transition metal-free conditions, a series of functionalized N-alkylated sulfonamides were prepared. This protocol also enabled the functionalization of pharmaceutical drugs bearing a sulfonamide or carboxylic acid moiety. This radical-mediated process allowed the assembly of three components including sulfonamides, redox active esters, and alkenes to yield complex sulfonamides in a one-pot manner.

Halogen-Bond-Induced Consecutive Csp3-H Aminations via Hydrogen Atom Transfer Relay Strategy

The utilization of a halogen bond in a number of chemical fields is well-known. Surprisingly, the incorporation of this useful noncovalent interaction in chemical reaction engineering is rare. We disclose here an uncommon use of halogen bonding to induce intermolecular Csp3-H amination while enabling a hydrogen atom transfer relay strategy to access privileged pyrrolidine structures directly from alkanes. Mechanistic studies support the presence of multiple halogen bond interactions at distinct reaction stages.

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.

Stereoinversion of Unactivated Alcohols by Tethered Sulfonamides

The direct, catalytic substitution of unactivated alcohols remains an undeveloped area of organic synthesis. Moreover, catalytic activation of this difficult electrophile with predictable stereo-outcomes presents an even more formidable challenge. Described herein is a simple iron-based catalyst system which provides the mild, direct conversion of secondary and tertiary alcohols to sulfonamides. Starting from enantioenriched alcohols, the intramolecular variant proceeds with stereoinversion to produce enantioenriched 2- and 2,2-subsituted pyrrolidines and indolines, without prior derivatization of the alcohol or solvolytic conditions.

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.

Organocatalytic nitrenoid transfer: Metal-free selective intermolecular C(sp3)-H amination catalyzed by an iminium salt

This report details the first organocatalytic method for nitrenoid transfer and its application to intermolecular, site-selective C(sp3)-H amination. The method utilizes a trifluoromethyl iminium salt as the catalyst, iminoiodinanes as the nitrogen source, and substrate as the limiting reagent. Activated, benzylic, and aliphatic substrates can all be selectively functionalized in yields up to 87%. A mechanistic proposal for the observed reactivity supported by experimental evidence invokes the intermediacy of a diaziridinium salt or related organic nitrenoid, species that have not been previously explored for the purpose of C-H amination. Finally, examples of late-stage functionalization of complex molecules highlight the selectivity and potential utility of this catalytic method in synthesis.

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

Direct Sulfonamidation of Primary and Secondary Benzylic Alcohols Catalyzed by a Boronic Acid/Oxalic Acid System

The direct sulfonamidation of primary and secondary benzylic alcohols catalyzed by a 2,3,4,5-tetrafluorophenylboronic acid/oxalic acid co-catalytic system was examined. The reaction proceeds under mild conditions with readily available starting materials and has been shown to be gram-scalable without significant decrease of yield. Both primary and secondary benzylic alcohols were evaluated and afforded the desired sulfonamide products with good to excellent yields.

Catalytic B(C6F5)3[rad]H2O-promoted defluorinative functionalization of tertiary aliphatic fluorides

A B(C6F5)3[rad]H2O-catalyzed defluorinative functionalization of tertiary aliphatic fluorides is described that proceeds under benign reaction conditions. The synthetic utility of the method is exemplified throu

Adamantane derivatives of sulfonamides: Sublimation, solubility, solvation and transfer processes in biologically relevant solvents

Eight adamantane derivatives of sulfonamides were synthesized and characterized. Temperature dependencies of saturation vapor pressure were obtained using the transpiration method and thermodynamic functions of the sublimation processes were calculated. S