17721-96-9

Usage

Uses

Used in Medicinal Chemistry:
2-nitroso-1,2,3,4-tetrahydroisoquinoline is used as a building block for the synthesis of pharmaceuticals, contributing to the development of new drugs and therapeutic agents.
Used in Organic Chemistry:
2-nitroso-1,2,3,4-tetrahydroisoquinoline is used as a component in the synthesis of various organic compounds, facilitating the creation of complex molecules and structures.
It is important to handle 2-nitroso-1,2,3,4-tetrahydroisoquinoline with care, as nitroso compounds can be potentially hazardous if not used and stored properly.

Upstream product

• 14099-81-1 1,2,3,4-tetrahydroisoquinoline 
• 91-21-4 1,2,3,4-tetrahydroisoquinoline 
• 155438-30-5 3,4-Dinitrofurazan 
• 2744-08-3 decahydroisoquinoline 

Downstream Products

• 4836-98-0 1,2,3,4-tetrahydro-2-amino-isoquinoline 
• 79492-26-5 2-amino-1,2,3,4-tetrahydro-isoquinoline-hydrochloride 
• 79492-45-8 2-(p-nitrobenzylideneamino)-1,2,3,4-tetrahydroisoquinoline 
• 19350-92-6 2-p-Toluenesulfonamido-1,2,3,4-tetrahydroisoquinoline 
• 79492-44-7 2-benzylideneamino-1,2,3,4-tetrahydroisoquinoline 
• 90872-67-6 N-methyl-3,4-dihydroisoquinolin-2(1H)-amine 

Relevant academic research and scientific papers

Synthesis of secondary and tertiary aminofurazans

Reactions of nitrofurazans with primary and secondary amines were studied. Conditions were found which allow the efficient replacement of the nitro group with these nucleophiles. Transformations of the amidoxime fragment, which is bound to the furazan ring and contains an amino substituent, enable one to substantially expand the spectrum of polyfunctional derivatives. The structures of the amines synthesized were studied by X-ray diffraction analysis.

The Use of Potassium/Sodium Nitrite as a Nitrosating Agent in the Electrooxidative N-Nitrosation of Secondary Amines

We report herein on the electrochemical N-nitrosation of secondary amines using widely available sodium/potassium nitrite as a nitrosating agent. This approach not only eliminates the need for using a combination of sodium/potassium and a strong acid but also has good functional group tolerance. The reaction is compatible with the late-stage modification of pharmaceutical compounds and could be conducted in gram scale with a high reaction efficiency. Preliminary mechanistic studies indicate that the N-nitrosation occurs via the anodic oxidation of KNO2 into an NO2 radical which is then transformed into an NO+ cation.

Electrochemical Nonacidic N-Nitrosation/N-Nitration of Secondary Amines through a Biradical Coupling Reaction

An acid-free N-nitrosation/nitration of the N?H bonds in secondary amines with Fe(NO3)3 ? 9H2O as the nitroso/nitro source through an electrocatalyzed radical coupling reaction was developed. Cyclic aliphatic amines and N-heteroaromatic compounds were N-nitrosated and N-nitrated, respectively, under mild conditions. Control and competition experiments, as well as kinetic studies, demonstrate that N-nitrosation and N-nitration involve two different radical reaction pathways involving N+ and N. radicals. Moreover, the electrocatalysis method enables the preferential activation of the N?H bond over the electrode and thus provides high selectivity for specific N atoms. Finally, this strategy exhibits a broad scope and provides a green and straightforward approach to generate useful N-nitroso/nitro compounds in good yields. (Figure presented.).

Substrate promiscuity of ortho-naphthoquinone catalyst: Catalytic aerobic amine oxidation protocols to deaminative cross-coupling and n-nitrosation

ortho-Naphthoquinone-based organocatalysts have been identified as versatile aerobic oxidation catalysts. Primary amines were readily cross-coupled with primary nitroalkanes via deaminative pathway to give nitroalkene derivatives in good to excellent yields. Secondary and tertiary amines were inert to ortho-naphthoquinone catalysts; however, secondary nitroalkanes were readily converted by ortho-naphthoquinone catalysts to the corresponding nitrite species that in situ oxidized the amines to the corresponding N-nitroso compounds. Without using harsh oxidants in a stoichiometric amount, the present catalytic aerobic oxidation protocol utilizes the substrate promiscuity feature to provide a facile access to amine oxidation products under mild reaction conditions.

Direct Transformation of Arylamines to Aryl Halides via Sodium Nitrite and N-Halosuccinimide

A one-pot universal approach for transforming arylamines to aryl halides via reaction with sodium nitrite (NaNO2) and N-halosuccinimide (NXS) in DMF at room temperature under metal- and acid-free condition is described. This new protocol that is complementary to the Sandmeyer reaction, is suggested to involve the in situ generation of nitryl halide induce nitrosylation of aryl amine to form the diazo intermediate which is halogenated to furnish the aryl halide.

Copper(II)-catalyzed oxidative N-nitrosation of secondary and tertiary amines with nitromethane under an oxygen atmosphere

The combination of a catalytic amount of Cu(OTf)2 and less than a stoichiometric amount of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) under an O2 atmosphere effectively promoted the N-nitrosation of both secondary aromatic/aliphatic amines and tertiary aromatic amines with nitromethane (CH3NO2) leading to the preparation of N-nitrosamine derivatives.

Iodide-catalyzed synthesis of N-nitrosamines via C-N cleavage of nitromethane

An iodide-catalyzed process to synthesize N-nitrosamines has been developed using TBHP as the oxidant. The mild catalytic system succeeded in cleaving the carbon-nitrogen bond in nitromethane. This methodology uses commercially available, inexpensive catalysts and oxidants and has a wide substrate scope and operational simplicity.

THERAPEUTIC AGENT FOR CEREBRAL INFARCTION

The invention provides a therapeutic drug for ischemic stroke. The therapeutic drug has the formula (I) wherein each symbol is as defined herein, or a pharmacologically acceptable salt thereof, or a solvate thereof, as an active ingredient.

PS-SNAP, a practical polymer-supported nitrosation reagent in organic synthesis

PS-SNAP was designed and evaluated as a practical nitrosating polymer-supported reagent for the nitrosation of sec-amines. Nitrosated dialkyl amines, alkyl anilines, and bis-anilines were obtained in good yields and high purities after shaking the corresponding amines in the presence of an excess of the newly described reagent followed by simple filtration and removal of solvents.

Bismuth chloride-sodium nitrite: A novel reagent for chemoselective N-nitrosation

Bismuth(III) chloride-sodium nitrite was used as a mild and efficient reagent for N-nitrosation of various tetrazoles, secondary amines, and amides under ambient conditions. Nitrosation took place chemoselectively at the nitrogen atom, giving corresponding N-nitroso derivatives in good to excellent yield. Copyright Taylor & Francis Group, LLC.