7678-64-0Relevant academic research and scientific papers
Reductive cyanation of organic chlorides using CO2 and NH3 via Triphos–Ni(I) species
Dong, Yanan,Li, Yuehui,Yang, Peiju,Zhao, Shizhen
, (2020/08/19)
Cyano-containing compounds constitute important pharmaceuticals, agrochemicals and organic materials. Traditional cyanation methods often rely on the use of toxic metal cyanides which have serious disposal, storage and transportation issues. Therefore, there is an increasing need to develop general and efficient catalytic methods for cyanide-free production of nitriles. Here we report the reductive cyanation of organic chlorides using CO2/NH3 as the electrophilic CN source. The use of tridentate phosphine ligand Triphos allows for the nickel-catalyzed cyanation of a broad array of aryl and aliphatic chlorides to produce the desired nitrile products in good yields, and with excellent functional group tolerance. Cheap and bench-stable urea was also shown as suitable CN source, suggesting promising application potential. Mechanistic studies imply that Triphos-Ni(I) species are responsible for the reductive C-C coupling approach involving isocyanate intermediates. This method expands the application potential of reductive cyanation in the synthesis of functionalized nitrile compounds under cyanide-free conditions, which is valuable for safe synthesis of (isotope-labeled) drugs.
Ni-Catalyzed Reductive Cyanation of Aryl Halides and Phenol Derivatives via Transnitrilation
Mills, L. Reginald,Graham, Joshua M.,Patel, Purvish,Rousseaux, Sophie A. L.
, p. 19257 - 19262 (2019/12/02)
Herein, we report a Ni-catalyzed reductive coupling for the synthesis of benzonitriles from aryl (pseudo)halides and an electrophilic cyanating reagent, 2-methyl-2-phenyl malononitrile (MPMN). MPMN is a bench-stable, carbon-bound electrophilic CN reagent that does not release cyanide under the reaction conditions. A variety of medicinally relevant benzonitriles can be made in good yields. Addition of NaBr to the reaction mixture allows for the use of more challenging aryl electrophiles such as aryl chlorides, tosylates, and triflates. Mechanistic investigations suggest that NaBr plays a role in facilitating oxidative addition with these substrates.
Ni-Mediated Generation of "cN" Unit from Formamide and Its Catalysis in the Cyanation Reactions
Yang, Luo,Liu, Yu-Ting,Park, Yoonsu,Park, Sung-Woo,Chang, Sukbok
, p. 3360 - 3365 (2019/03/26)
The in situ generation of a "cyano" unit from readily available organic precursors is of high interest in synthetic chemistry. Herein, we report the first example of Ni-mediated dehydration of formamide to form "CN" and its subsequent catalytic applications in the hydrocyanation of alkynes and cyanation of aryl halides. Formamide can serve as a convenient source for the nitrile unit, in that it releases water as the only byproduct.
Phenothiazine compounds
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, (2008/06/13)
The present invention relates to compounds of the formula (I): STR1 or a salt, ester or amide thereof; wherein R1 is a C1-7 bivalent aliphatic hydrocarbon group or a single bond; R2 and R3 are the same or different and are each hydrogen, C1-4 alkyl or taken together with the nitrogen comprise a nitrogen-containing heterocyclic ring having four to six ring members; R4 is hydrogen, halogen, C1-4 alkoxy, C1-4 alkyl optionally substituted by one to three halogen atoms; or a group R1 CO2 H as hereinbefore defined; and A is C1-4 alkylene or ANR2 R3 forms a group --CH2 --(CH2)2 or CH2 --(CH2)2 B is an acidic group other than a mono-carboxylic acid group of comparable or greater acid strength than a carboxylic acid group in a similar chemical environment, provided that any sulphonamide group contains at least one N-H bond. Also disclosed are processes for the preparation of the compounds of the formula (I), chemical intermediates for use in their preparation, and pharmaceutical formulations containing the said compounds. The compounds have antiallergic activity as defined by blockade of anaphylactoid activity. Certain of the compounds also have good antihistaminic activity.
