Category: 37812-51-4

A Base- and Metal-free Protocol for the Synthesis of 2-Aryl/heteroaryl Thiazolines was written by Chaudhary, Shweta;Milton, Marilyn D.;Garg, Parul. And the article was included in ChemistrySelect in 2017.Formula: C12H14N2O This article mentions the following:

A simple and efficient base- and metal-free protocol for the synthesis of 2-aryl/heteroarylthiazolines I [Ar = 4-BrC₆H₄, 4-n-BuHNCH₂C₆H₄, 2-pyridyl, etc.; R = H, CO₂Et] from aryl/heteroaryl nitriles and cysteamine hydrochloride was reported. This method was applicable to a series of aryl/heteroaryl nitriles containing different substituents such as halides, amines, substituted azoles, etc. and furnishing the corresponding thiazolines in up to 99% yields. A selective synthesis of mono- or bis-thiazoline in more than 90% yield was also observed by modifying the duration of the reaction. A probable reaction mechanism involving the formation of highly activated arylimino chloride was also given. In the experiment, the researchers used many compounds, for example, 4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4Formula: C12H14N2O).

4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4) belongs to nitriles. There has been no report on the microbial biosynthesis of nitriles and the physiological function of such enzymes, nor was it not even known whether aliphatic and aromatic nitriles are biological compounds or just petrochemicals. In conventional organic reductions, nitrile is reduced by treatment with lithium aluminium hydride to the amine. Reduction to the imine followed by hydrolysis to the aldehyde takes place in the Stephen aldehyde synthesis, which uses stannous chloride in acid.Formula: C12H14N2O

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Identification, Design and Biological Evaluation of Heterocyclic Quinolones Targeting Plasmodium falciparum Type II NADH:Quinone Oxidoreductase (PfNDH2) was written by Leung, Suet C.;Gibbons, Peter;Amewu, Richard;Nixon, Gemma L.;Pidathala, Chandrakala;Hong, W. David;Pacorel, Benedicte;Berry, Neil G.;Sharma, Raman;Stocks, Paul A.;Srivastava, Abhishek;Shone, Alison E.;Charoensutthivarakul, Sitthivut;Taylor, Lee;Berger, Olivier;Mbekeani, Alison;Hill, Alasdair;Fisher, Nicholas E.;Warman, Ashley J.;Biagini, Giancarlo A.;Ward, Stephen A.;O’Neill, Paul M.. And the article was included in Journal of Medicinal Chemistry in 2012.Application In Synthesis of 4-(Morpholinomethyl)benzonitrile This article mentions the following:

Following a program undertaken to identify hit compounds against NADH:ubiquinone oxidoreductase (PfNDH2), a novel enzyme target within the malaria parasite Plasmodium falciparum, hit to lead optimization led to identification of CK-2-68, a mol. suitable for further development. To reduce ClogP and improve solubility of CK-2-68 incorporation of a variety of heterocycles, within the side chain of the quinolone core, was carried out, and this approach led to a lead compound SL-2-25 (I). I has IC₅₀s in the nanomolar range vs. both the enzyme and whole cell P. falciparum (IC₅₀ = 15 nM PfNDH2; IC₅₀ = 54 nM (3D7 strain of P. falciparum)) with notable oral activity of ED₅₀/ED₉₀ of 1.87/4.72 mg/kg vs. Plasmodium berghei (NS Strain) in a murine model of malaria when formulated as a phosphate salt. Analogs in this series also demonstrate nanomolar activity against the bc₁ complex of P. falciparum providing the potential added benefit of a dual mechanism of action. The potent oral activity of 2-pyridyl quinolones underlines the potential of this template for further lead optimization studies. In the experiment, the researchers used many compounds, for example, 4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4Application In Synthesis of 4-(Morpholinomethyl)benzonitrile).

4-(Morpholinomethyl)benzonitrile (cas: 37812-51-4) belongs to nitriles. Nitrile compounds can be prepared by the incorporation of a cyanide source through C–C bond formation or by dehydration of primary carboxamides. Asymmetric bioreduction of nitriles is an attractive route to produce optically active nitriles as current metal-catalyzed hydrogenations tend to have low reactivity.Application In Synthesis of 4-(Morpholinomethyl)benzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts