120972-13-6

Usage

Uses

Used in Organic Synthesis:
N-IodoMorpholine hydriodide is used as an iodinating agent for the synthesis of various organic compounds. It is particularly useful for the preparation of phosphine oxide-iodotriazole hybrid molecules, silver bis(pyrazolyl)-methane complex based supramolecular architectures, and iodo-1,4-naphthoquinones.
Used in Pharmaceutical Industry:
N-IodoMorpholine hydriodide is used as a key intermediate in the synthesis of biologically significant 3-aryl-1,4-naphthoquinones, which have potential applications in the development of new drugs and therapeutic agents.
Used in Chemical Research:
N-IodoMorpholine hydriodide is used as a reagent in various chemical research studies, enabling the exploration of new chemical reactions and the development of innovative synthetic methods. Its ability to introduce iodine atoms into molecules makes it a valuable tool for understanding the properties and behavior of iodinated compounds.

Upstream product

• 110-91-8 morpholine 

Downstream Products

• 5455-91-4 3,4-dimorpholino-4-phenylbutan-2-one 
• 1450803-93-6 C₁₉H₁₉NO₃ 
• 6339-26-0 4-tosylmorpholine 
• 5650-45-3 2-(morpholin-4-yl)-1-phenylpropan-1-one 

Relevant academic research and scientific papers

A metal-free amination of benzoxazoles - The first example of an iodide-catalyzed oxidative amination of heteroarenes

An efficient transition-metal-free amination of benzoxazoles has been developed. With catalytic amounts of tetrabutylammoniumiodide (TBAI), aqueous solutions of H2O2 or TBHP as co-oxidant and under mild reaction conditions, highly desirable 2-aminobenzoxazoles were isolated in excellent yields of up to 93%. First mechanistic experiments indicate the in situ iodination of the secondary amine as the putative mode of activation.

P2X7 receptor inhibition by 2-amino-3-aryl-1,4-naphthoquinones

Extracellular ATP activates purinergic receptors such as P2X7, cationic channels for Ca2+, K+, and Na+. There is robust evidence of the involvement of these receptors in the immune response, so P2X7 receptors (P2X7R) are considered a potential therapeutic target for the development of anti-inflammatory drugs. Although there are many studies of the anti-inflammatory properties of naphthoquinones, these molecules have not yet been explored as P2X7 antagonists. In previous work, our group prepared 3-substituted (halogen or aryl) 2-hydroxy-1,4-naphthoquinones and studied their action on P2X7R. In this paper, eight 2-amino-3-aryl-1,4-naphthoquinones were evaluated to identify the inhibitory activity on P2X7R and the toxicological profile. Three analogues (AD-4CN, AD-4Me, and AD-4F) exhibited reduced toxicity for mammalian cells with CC50 values higher than 500 μM. These three 3-substituted 2-amino-1,4-naphthoquinones inhibited murine P2X7R (mP2X7R) in vitro. However, the analogues AD-4CN and AD-4Me showed low selectivity index values. AD-4F inhibited both mP2X7R and human P2X7R (hP2X7R) with IC50 values of 0.123 and 0.93 μM, respectively. Additionally, this analogue exhibited higher potency than BBG at inhibiting the ATP-induced release of IL-1β in vitro. Carrageenan-induced paw edema in vivo was reversed for AD-4F with an ID50 value of 11.51 ng/kg. Although AD-4F was less potent than previous 3-substituted (halogen or aryl) 2-hydroxy-1,4-naphthoquinones such as AN-04 in vitro, this 3-substituted 2-amino-1,4-naphthoquinone revealed higher potency in vivo to reduce the edematogenic response. In silico analysis suggests that the binding site of the novel 2-amino-3-aryl-1,4-naphthoquinone derivatives, including all the tautomeric forms, is located in the pore area of the hP2X7R model. Based on these results, we considered AD-4F to be a satisfactory P2X7R inhibitor. AD-4F might be used as a scaffold structure to design a novel series of inhibitors with potential inhibitory activity on murine (mP2X7R) and human (hP2X7R) P2X7 receptors.

Synthesis, characterization and biological activities of 3-aryl-1,4-naphthoquinones-green palladium-catalysed Suzuki cross coupling

Quinones are important scaffolds that are present in a variety of natural products or synthetic bioactive molecules. Arylation is an important strategy for accomplishing structural modifications, leading to new potential candidates for use as drugs. In the present work, palladium-catalysed, ligandless and phosphine-free Suzuki coupling reactions between 2-hydroxy-3-iodo-1,4-naphthoquinone and boronic acids were employed to prepare several 2-hydroxy-3-aryl-1,4-naphthoquinones in aqueous conditions using microwave irradiation or conventional heating. Because of the biological activities of quinones, which are related to their ability to accept electrons to form semiquinones and hydroquinones, the electrochemical behaviour of the synthesized molecules was investigated. The Osiris and Molinspiration Cheminformatics programs, utilizing in silico analyses, imply that these naphthoquinones are candidates for use as drugs which was reinforced by the outcomes of the in vitro antifungal and trypanocidal activity tests. Our in vitro data indicated a MIC value of 8 μg mL-1 against Candida albicans ATCC 24433 strains, and an EC50 of 0.67 μM with respect to trypanocidal activity against Trypanosoma cruzi epimastigote strains (Y).

Sulfonamide formation from sodium sulfinates and amines or ammonia under metal-free conditions at ambient temperature

A novel, practical and highly efficient method for the construction of a variety of sulfonamides mediated by I2 was demonstrated. The reaction proceeds readily at room temperature using a variety of sodium sulfinates and amines or ammonia in water in a metal-, base-, ligand-, or additive-free protocol. Primary, secondary and tertiary sulfonamides were obtained in good to excellent yields with a broad range of functional group tolerability. This journal is

A practical and general ipso iodination of arylboronic acids using N-iodomorpholinium iodide (NIMI) as a novel iodinating agent: mild and regioselective synthesis of aryliodides

A mild and efficient protocol for the ipso-iodination of aryl boronic acids using N-iodomorpholinium iodide (NIMI) generated in situ from morpholine and molecular iodine as a novel iodinating agent has been developed. The addition of a catalytic amount of copper iodide found to promote rate enhancement of the iodination reaction and dramatic increase in the yield depending upon the nature of the boronic acid was observed. The mechanistic study revealed that depending upon the nature of the substrate, either the classical ipso substitution or copper catalysed iododeborylation pathway overall dominates the present iodination reaction. The features such as mild reaction conditions, operational simplicity, high to excellent yields, excellent functional group compatibility and low catalyst loading make this method potentially useful in organic synthesis.

Ruthenium-catalyzed cycloadditions of 1-haloalkynes with nitrile oxides and organic azides: Synthesis of 4-haloisoxazoles and 5-halotriazoles

(Cyclopentadienyl)(cyclooctadiene) ruthenium(II) chloride [CpRuCl(cod)] catalyzes the reaction between nitrile oxides and electronically deficient 1-choro-, 1-bromo-, and 1-iodoalkynes leading to 4-haloisoxazoles. Organic azides are also suitable 1,3-dipoles, resulting in 5-halo-1,2,3-triazoles. These air-tolerant reactions can be performed at room temperature with 1.25 equivalents of the respective 1,3-dipole relative to the alkyne component. Reactive 1-haloalkynes include propiolic amides, esters, ketones, and phosphonates. Post-functionalization of the halogenated azole products can be accomplished by using palladium-catalyzed cross-coupling reactions and by manipulation of reactive amide groups. The lack of catalysis observed with [Cp RuCl(cod)] (Cp=pentamethylcyclopentadienyl) is attributed to steric demands of the Cp* (η5-C5Me5) ligand in comparison to the parent Cp (η5-C5H5). This hypothesis is supported by the poor reactivity of [(η5-C 5Me4CF3)RuCl(cod)], which serves as a an isosteric mimic of Cp* and as an isoelectronic analogue of Cp.

A novel and metal-free approach towards α-ketoamides using a TBHP/I2-promoted tandem reaction of amines with β-diketones via C-C bond cleavage

A novel approach towards the synthesis of α-ketoamides using a TBHP/I2-promoted tandem reaction of amines with β-diketones via C-C bond cleavage has been developed. This one-pot reaction proceeded well under metal-free conditions and generated

COPPER CATALYZED CYCLOADDITION OF ORGANIC AZIDES AND 1-HALOALKYNES

This invention provides a method for preparing a 1,2,3-triazole compound comprising contacting an organic azide with a 2-substitued-1-haloalkyne, in the presence of a copper catalyst and a copper-coordinating ligand (preferably a tertiary amine) in a liquid reaction medium, thereby forming a 1,4,5-substituted-1,2,3-triazole compound including a halo substituent at the 5-position of the triazole, the organic portion of the organic azide at the 1-position of the triazole, and the substituent of the 1-iodoalkyne at the 4-position of the triazole. A method for preparing 1-iodoalkynes is also provided.

An alkynyliodide cycloaddition strategy for the construction of iodoisoxazoles

(Figure presented) The thermally promoted cycloaddition between alkynyliodides and nitrile oxides is reported. The process offers excellent regioselectivity and a broad scope with respect to both the iodoalkynes and chloro-oximes. Further functionalization of the highly decorated iodoisoxazole motifs can be achieved via Suzuki cross-coupling.

Copper(I)-catalyzed cycloaddition of organic azides and 1-iodoalkynes

High fidelity: 1-Iodoalkynes react rapidly and selectively with organic azides in the presence of copper(I) catalysts (see scheme; TTTA=tris((1-tert- butyl-1H-1,2,3-triazolyl)methyl)amine). The reaction is compatible with many functional groups and solven