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On September 1, 1981, Yamashita, Yoshiro; Suzuki, Daisuke; Masumura, Mitsuo published an article.Quality Control of 2-((1H-Indol-3-yl)methylene)malononitrile The title of the article was Synthesis of vinyl-substituted indolizine derivatives by a novel reaction of indolizines with ethoxyethylenes having electron-withdrawing substituents. And the article contained the following:

The vinylindolizines I (R1 = Me, Ph, p-BrC6H4; R2, R3 = H, Me; R4 = R5 = CN, CO2Et, R4 = CN, COMe; R5 = CO2Et) were prepared in 22-85% yields by Michael addition of the indolizines II with EtOCH:CR4R5. Hydrolysis of I (R1 = Ph, R2 = H, Me; R3 = H, R4 = R5 = CN) gave the corresponding 3-formylindolizines. Pyrrole and 1-methylpyrrole underwent similar addition with EtOCH:C(CN)2 to give the pyrroles III (R = H, Me). The experimental process involved the reaction of 2-((1H-Indol-3-yl)methylene)malononitrile(cas: 75629-62-8).Quality Control of 2-((1H-Indol-3-yl)methylene)malononitrile

The Article related to indolizine addition ethoxyethylene, vinylindolizine, Heterocyclic Compounds (One Hetero Atom): Other Areno- and Diarenopyridines (Including Also Quinuclidines, etc.) and other aspects.Quality Control of 2-((1H-Indol-3-yl)methylene)malononitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On April 18, 2019, Jung, Won-Hyuk published a patent.Application of 1160936-51-5 The title of the patent was Preparation of phenylacetylene derivatives as inhibitors against interaction between PD-1 and PD-L1. And the patent contained the following:

The invention relates to compounds of formula I or pharmaceutically acceptable salts thereof that are useful for the prevention and treatment of cancer or autoimmune disease as inhibitors against interaction between programmed death 1 (PD-1) and programmed death-ligand 1 (PD-L1). Compounds of formula I wherein X1=X2 is N=C-R11, R11-C=N, N=N, or C=C; R1 is (CH)n-CO2H, O-R9, CO-(NH-R9), CO-R9, NH-R9, N(R9)2, N(R9)(R10), etc.; n is 0-4; R2 is H, halo, alkyl, cyano, hydroxy, amino, CO-alkyl, O-alkyl, O-(CH2)m-heteroaryl, O-(CH2)m-cycloalkyl, O-(CH2)m-heterocyclyl, NH-alkyl, etc.; m is 0-4; R3, R6, R7, R8, and R11 are independently H, halo, alkyl, cyano, hydroxy, amino, O-alkyl, NH-alkyl, etc.; R4 is H, halo, alkyl, cyano, hydroxy, amino, O-alkyl, NH-alkyl, CO-alkyl, etc.; R5 is (un)substituted (hetero)aryl, (un)substituted cycloalkyl, or (un)substituted heterocyclyl; R9 and R10 are independently (un)substituted alkyl; are claimed. Example compound II was prepared via Sonogashira coupling reaction of Me 6-ethynylpyridazine-3-carboxylate with 3-bromo-2-methyl-[1,1′-biphenyl], followed by Dibal-H reduction, reductive amination with Me glycinate hydrochloride, and basic hydrolysis. The invention compounds were evaluated for the inhibitory activity against interaction between PD-1 and PD-L1 (biol. activity given). The experimental process involved the reaction of 5-Bromo-3-hydroxypicolinonitrile(cas: 1160936-51-5).Application of 1160936-51-5

The Article related to phenylacetylene derivative preparation pd1 pdl1 inhibition cancer autoimmune disease, Benzene, Its Derivatives, and Condensed Benzenoid Compounds: Hydrocarbons (Saturated and Unsaturated Side Chains) and other aspects.Application of 1160936-51-5

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On April 23, 2019, Jung, Won Hyeok published a patent.Name: 5-Bromo-3-hydroxypicolinonitrile The title of the patent was Preparation of phenylacetylene derivatives as inhibitors against interaction between PD-1 and PD-L1. And the patent contained the following:

The invention relates to compounds of formula I or pharmaceutically acceptable salts thereof that are useful for the prevention and treatment of cancer or autoimmune disease as inhibitors against interaction between programmed death 1 (PD-1) and programmed death-ligand 1 (PD-L1). Compounds of formula I wherein X1=X2 is N=C-R11, R11-C=N, N=N, or C=C; R1 is (CH)n-CO2H, O-R9, CO-(NH-R9), CO-R9, NH-R9, N(R9)2, N(R9)(R10), etc.; n is 0-4; R2 is H, halo, alkyl, cyano, hydroxy, amino, CO-alkyl, O-alkyl, O-(CH2)m-heteroaryl, O-(CH2)m-cycloalkyl, O-(CH2)m-heterocyclyl, NH-alkyl, etc.; m is 0-4; R3, R6, R7, R8, and R11 are independently H, halo, alkyl, cyano, hydroxy, amino, O-alkyl, NH-alkyl, etc.; R4 is H, halo, alkyl, cyano, hydroxy, amino, O-alkyl, NH-alkyl, CO-alkyl, etc.; R5 is (un)substituted (hetero)aryl, (un)substituted cycloalkyl, or (un)substituted heterocyclyl; R9 and R10 are independently (un)substituted alkyl; are claimed. Example compound II was prepared via Sonogashira coupling reaction of Me 6-ethynylpyridazine-3-carboxylate with 3-bromo-2-methyl-[1,1′-biphenyl], followed by Dibal-H reduction, reductive amination with Me glycinate hydrochloride, and basic hydrolysis. The invention compounds were evaluated for the inhibitory activity against interaction between PD-1 and PD-L1 (biol. activity given). The experimental process involved the reaction of 5-Bromo-3-hydroxypicolinonitrile(cas: 1160936-51-5).Name: 5-Bromo-3-hydroxypicolinonitrile

The Article related to phenylacetylene derivative preparation pd1 pdl1 inhibition cancer autoimmune disease, Benzene, Its Derivatives, and Condensed Benzenoid Compounds: Hydrocarbons (Saturated and Unsaturated Side Chains) and other aspects.Name: 5-Bromo-3-hydroxypicolinonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On March 31, 2016, Muhammad, Munira T.; Khan, Khalid M.; Taha, Muhammad; Khan, Tariq; Hussain, Shafqat; Fakhri, Muhammad I.; Perveen, Shahnaz; Voelter, Wolfgang published an article.Safety of 2-((1H-Indol-3-yl)methylene)malononitrile The title of the article was New Facile, Eco-Friendly and Rapid Synthesis of Trisubstituted Alkenes Using Bismuth Nitrate as Lewis Acid. And the article contained the following:

A facile, eco-friendly and rapid method for Knoevenagel condensations using bismuth nitrate as Lewis acid was presented. In a typical reaction, 1 mmol of aromatic aldehyde with 1.1 mmol of malanonitrile in the presence of bismuth nitrate (3 mmol%) was refluxed in water (10 mL) for 25-30 min. In order to generalize the newly developed methodol., a variety of aldehydes were selected to synthesize different trisubstituted alkenes and it was found that this method can also be applied on aromatic aldehydes. For comparison purposes, the reaction was carried out in ethanol in parallel to water and found that water is the best solvent for this reaction. The advantages of bismuth nitrate as a catalyst were: easy to remove from the reaction mixture by simple filtration, recyclable, required water as solvent, was eco-friendly and afforded high yields (90-97%). The experimental process involved the reaction of 2-((1H-Indol-3-yl)methylene)malononitrile(cas: 75629-62-8).Safety of 2-((1H-Indol-3-yl)methylene)malononitrile

The Article related to aryl aldehyde malononitrile bismuth nitrate catalyst knoevenagel condensation, arylidene malononitrile preparation green chem, Benzene, Its Derivatives, and Condensed Benzenoid Compounds: Hydrocarbons (Saturated and Unsaturated Side Chains) and other aspects.Safety of 2-((1H-Indol-3-yl)methylene)malononitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On January 31, 2022, Chakraborty, Sourav; Rudra Paul, Abhijit; Majumdar, Swapan published an article.Name: 2-((1H-Indol-3-yl)methylene)malononitrile The title of the article was Base and metal free true recyclable medium for Knoevenagel condensation reaction in SDS-ionic liquid-aqueous miceller composite system. And the article contained the following:

This paper presents for the first time a base and metal free procedure for Knoevenagel condensation reaction in a neutral medium comprises water-SDS-imidazolium ionic liquid composite system. Knoevenagel condensation products from the different aromatic aldehydes and active methylene compounds such as malononitrile, Et cyanoacetate or cyano acetic acid provides good to excellent yields in all cases examined at 80掳C. The developed protocol has several advantages such as chromatog. and organic volatile solvent free protocol, short reaction time and recyclability of catalyst including reaction waste. The reaction is believed to proceed in the hydrophobic cavity of the micelle formed in the medium which was proved by dynamic light scattering studies. The experimental process involved the reaction of 2-((1H-Indol-3-yl)methylene)malononitrile(cas: 75629-62-8).Name: 2-((1H-Indol-3-yl)methylene)malononitrile

The Article related to aryl aldehyde active methylene compound knoevenagel condensation green chem, sds ionic liquid aqueous miceller composite system, Benzene, Its Derivatives, and Condensed Benzenoid Compounds: Hydrocarbons (Saturated and Unsaturated Side Chains) and other aspects.Name: 2-((1H-Indol-3-yl)methylene)malononitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Badiger, Krishnappa B.; Kamanna, Kantharaju published an article in 2021, the title of the article was Knoevenagel condensation reaction catalysed by agro-waste extract as a greener solvent catalyst.Name: 2-((1H-Indol-3-yl)methylene)malononitrile And the article contains the following content:

This paper present a novel Knoevenagel reaction protocol for the condensation of aromatic/heteroaromatic aldehydes RCHO (R = 2-phenylethenyl, naphthalen-1-yl, furan-2-yl, 1H-indol-3-yl, etc.) with malononitrile to give 伪, 尾-unsaturated benzylidene derivs RCH=C(CN)2. The main focus of this work is to reveal the usability of agro-waste extracts as a catalyst in the Knoevenagel condensation. In addition, the present method describes direct isolation of the formed products without using organic solvent extraction and gives good yields product. The experimental process involved the reaction of 2-((1H-Indol-3-yl)methylene)malononitrile(cas: 75629-62-8).Name: 2-((1H-Indol-3-yl)methylene)malononitrile

The Article related to unsaturated benzylidene preparation green chem, aryl aldehyde malononitrile knoevenagel condensation agro waste extract catalyst, Benzene, Its Derivatives, and Condensed Benzenoid Compounds: Hydrocarbons (Saturated and Unsaturated Side Chains) and other aspects.Name: 2-((1H-Indol-3-yl)methylene)malononitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Pippal, Parveen; Singh, Prabal Pratap published an article in 2017, the title of the article was Calcium ferrite, an efficient catalyst for Knoevenagel condensation (A green approach).Quality Control of 2-((1H-Indol-3-yl)methylene)malononitrile And the article contains the following content:

Calcium ferrite NPs catalyst were used as a cheaper and highly efficient catalyst for Knoevenagel condensation of active methylene substrates with various carbonyl compounds affording condensed products in excellent yields in shorter reaction time. The developed greener protocol was very simple, involving cleaner work up and the synthesized products did not require further purification The catalyst was easily removed and reused at least for four times without any appreciable change in reactivity. The experimental process involved the reaction of 2-((1H-Indol-3-yl)methylene)malononitrile(cas: 75629-62-8).Quality Control of 2-((1H-Indol-3-yl)methylene)malononitrile

The Article related to aryl aldehyde active methylene compound calcium ferrite knoevenagel condensation, cyanoalkene preparation green chem, calcium ferrite catalyst preparation crystallinity, Benzene, Its Derivatives, and Condensed Benzenoid Compounds: Hydrocarbons (Saturated and Unsaturated Side Chains) and other aspects.Quality Control of 2-((1H-Indol-3-yl)methylene)malononitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

On November 30, 1988, Matsuo, Masaaki; Tsuji, Kiyoshi; Konishi, Nobukiyo; Okumura, Hiroyuki published a patent.Application In Synthesis of 3-Chloro-4-nitrobenzonitrile The title of the patent was Preparation of alkanesulfonanilides as analgesics and antiinflammatories. And the patent contained the following:

The title compounds [I; Ar = Q; R1 = alkyl, haloalkyl; R2 = acyl, cyano, CO2H, (un)substituted alkyl, etc.; R3 = H, NO2, alkyl, halo; R4-R7 = H, halo, haloalkyl, alkoxy, (un)substituted heterocyclyl; X = S(O)n, NHCO, CONH, R8N, R9CH; R8 = H, alkyl; R9 = H, OH; n = 0-2] and their pharmaceutically acceptable salts were prepared NaBH4 was added to 4′-acetyl-2′-[(2,4-difluorophenyl)thio]methanesulfonanilide in MeOH, and the mixture stirred overnight at room temperature and treated with AcOH to give 2′-[(2,4-difluorophenyl)thio]-4′-(1-hydroxyethyl)methanesulfonanilide (II). In rats 10 mg II/kg orally gave 90.1% inhibition of secondary lesions induced by Mycobacterium聽tuberculosis, a measure of antiinflammatory activity. 4′-Acetyl-2′-[(2,4-difluorophenyl)amino]methanesulfonanilide, also prepared, had an analgsic ED50 of 1.8 mg/kg orally in the mouse writhing test. The experimental process involved the reaction of 3-Chloro-4-nitrobenzonitrile(cas: 34662-29-8).Application In Synthesis of 3-Chloro-4-nitrobenzonitrile

The Article related to alkanesulfonanilide preparation analgesic antiinflammatory, Benzene, Its Derivatives, and Condensed Benzenoid Compounds: Sulfenic, Sulfinic, and Sulfonic Acids and Derivatives and other aspects.Application In Synthesis of 3-Chloro-4-nitrobenzonitrile

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts