Month: November 2022

Taylor, Edward C.; Perlman, Katherine L.; Kim, Young-Ho; Sword, Ian P.; Jacobi, Peter A. published an article in 1973, the title of the article was Pteridines. XXIX. Unequivocal route to 2,4-diamino-6-substituted pteridines.Synthetic Route of 5098-14-6 And the article contains the following content:

2,4-Diamino-6-substituted pteridines (I) are prepared Reaction of an α-keto-aldoxime with aminomalononitrile gives 2-amino-3-cyano-5-substituted pyrazine 1-oxides which yield 2,4-diamino-6-substituted pteridine 8-oxides upon cyclization with guanidine. 2,4-Diaminopteridines are then obtained by deoxygenation of the corresponding 8-oxides, or alternately by prior deoxygenation of these pyrazine 1-oxides, followed by cyclization with guanidine. The conversion of 2-amino-3-cyano-5-methylpyrazine 1-oxide to the corresponding 1,4-dioxide, and a number of chem. transformations of this latter intermediate, are also described. The experimental process involved the reaction of 2-Aminomalononitrile 4-methylbenzenesulfonate(cas: 5098-14-6).Synthetic Route of 5098-14-6

The Article related to pteridine diamino preparation, aminopteridine preparation, Heterocyclic Compounds (More Than One Hetero Atom): Purines and Pteridines and other aspects.Synthetic Route of 5098-14-6

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Taylor, Edward C.; Abdulla, Riaz F. published an article in 1973, the title of the article was Pteridines. XXXI. New and unequivocal synthesis of isoxanthopterin-6-carboxylic acid (Cyprino-Pourpre B).COA of Formula: C10H11N3O3S And the article contains the following content:

Condensation of HC(CN)2NH2 with HON:CHCOCH:NOH gave 2-amino-3-cyano-5-oximinomethylpyrazine 1-oxide which cyclized with guanidine to the pteridine oxide (I). Heating I in POCl3-DMF gave the chloronitrile (II) which under reflux in aqueous NaOH gave isoxanthopterin-6-carboxylic acid (III). The experimental process involved the reaction of 2-Aminomalononitrile 4-methylbenzenesulfonate(cas: 5098-14-6).COA of Formula: C10H11N3O3S

The Article related to pteridine, isoxanthopterincarboxylic acid, cyprino pourpre b, Heterocyclic Compounds (More Than One Hetero Atom): Purines and Pteridines and other aspects.COA of Formula: C10H11N3O3S

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On April 16, 2021, Reutskaya, Elena; Sapegin, Alexander; Peintner, Stefan; Erdelyi, Mate; Krasavin, Mikhail published an article.Synthetic Route of 34662-29-8 The title of the article was Sulfur Oxidation Increases the Rate of HIRE-Type [1.4]Thiazepinone Ring Expansion and Influences the Conformation of a Medium-Sized Heterocyclic Scaffold. And the article contained the following:

The hydrated imidazoline ring expansion (HIRE-type) reaction was investigated for a series of di(hetero)arene-fused [1.4]thiazepinones in comparison with their sulfone counterparts. The sulfones were found to undergo ring expansion at a much higher rate compared to the thioethers, much in line with the current mechanistic understanding of the process. Moreover, the amide bond cis- and trans-isomers of the ring-expanded products were found, in the case of sulfones, to be stabilized through an intramol. hydrogen bond. The latter phenomenon was studied in detail by NMR experiments and corroborated by X-ray crystallog. information. The experimental process involved the reaction of 3-Chloro-4-nitrobenzonitrile(cas: 34662-29-8).Synthetic Route of 34662-29-8

The Article related to thiazepinone hydrated imidazoline ring expansion conformation sulfone, Heterocyclic Compounds (More Than One Hetero Atom): Other 7-Membered Rings and other aspects.Synthetic Route of 34662-29-8

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Taylor, Edward C.; Jacobi, Peter A. published an article in 1975, the title of the article was Pteridines. XXXIV. Synthesis of 8-hydroxy-7(8H)-pteridinones (pteridine hydroxamic acids).Reference of 2-Aminomalononitrile 4-methylbenzenesulfonate And the article contains the following content:

A series of 2,4-diamino-6-alkyl-substituted 8-hydroxy-7(8H)-pteridinones (pteridinehydroxamic acids) (I) was prepared from 2,4-diamino-6-substituted pteridine 8-oxides by chlorination in glacial AcOH, followed by cleavage of the resulting pteridinehydroxamic acid anhydrides II with ethanolic HCl. An alternative but less satisfactory route to 2,4-diamino-6-methyl-8-hydroxy-7(8H)-pteridinone involved condensation of pyruvohydroxamoyl chloride with aminomalononitrile tosylate to give 2-amino-3-cyano-5-methyl-6-chloropyrazine 1-oxide, hydrolysis to the pyrazinehydroxamic acid III, and cyclization with guanidine. The experimental process involved the reaction of 2-Aminomalononitrile 4-methylbenzenesulfonate(cas: 5098-14-6).Reference of 2-Aminomalononitrile 4-methylbenzenesulfonate

The Article related to aminopteridinone, pteridinehydroxamic acid, pteridinone amino, hydroxamic acid pteridine, Heterocyclic Compounds (More Than One Hetero Atom): Purines and Pteridines and other aspects.Reference of 2-Aminomalononitrile 4-methylbenzenesulfonate

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Nitrile – Wikipedia,
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Watson, Angus A. published an article in 1977, the title of the article was Purine N-oxides. 66. Synthesis of 9-hydroxyadenine.Quality Control of 2-Aminomalononitrile 4-methylbenzenesulfonate And the article contains the following content:

The synthesis of 9-hydroxyadenine (I, R = H), by a variation of the Shaw purine synthesis, involved the condensation of Et N-(dicyanomethyl)formimidate tosylate with benzyloxyamine to a cyanoimidazole derivative II (R = H), which was then ring-closed to III (R = H) and hydrolyzed to the desired purine derivative This is the 3rd adenine N-oxide isomer available for carcinogenicity testing. Analogously prepared was I (R = Me). The experimental process involved the reaction of 2-Aminomalononitrile 4-methylbenzenesulfonate(cas: 5098-14-6).Quality Control of 2-Aminomalononitrile 4-methylbenzenesulfonate

The Article related to hydroxyadenine carcinogen, adenine hydroxy, cyanoimidazole cyclization, imidazole cyano cyclization, Heterocyclic Compounds (More Than One Hetero Atom): Purines and Pteridines and other aspects.Quality Control of 2-Aminomalononitrile 4-methylbenzenesulfonate

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Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Taylor, Edward C.; Kobayashi, T. published an article in 1976, the title of the article was Pteridines. XXXIX. Synthesis of 2,4-diamino-7-alkenylpteridines and their 8-oxides.Application of 5098-14-6 And the article contains the following content:

A versatile and flexible route to a variety of 2,4-diamino-7-alkenylpteridines was described. Condensation of aminomalononitrile with α-oximino-β-chloroaldehydes R1COC(:NOH)CClR2R3 [R1-R3 = H; R1 = R2 = H, R3 = Me, Pr; R1R2 = (CH2)3, R3 = H] (prepared by the addition of nitrosyl chloride to α,β-unsaturated aldehydes) gave 2-amino-3-cyano-6-(1-chloroalkyl)pyrazine 1-oxides I. The 6-chloromethyl compound I (R1-R3 = H) was converted to a stable phosphorane which was condensed with aldehydes to give a series of 2-amino-3-cyano-6-alkenylpyrazine 1-oxides II (R = Me, CH2OH, CO2H, Ph, 3,4-Cl2C6H3, 3,4-(OCH2O)C6H3, 2-thienyl, 3-pyridyl) which were cyclized with guanidine to 2,4-diamino-7-alkenylpteridine 8-oxides III (n = 1). Deoxygenation of I (R1-R3 = H) with PCl3 in THF gave 2-amino-3-cyano-6-chloromethylpyrazine, which analogously gave a series of 2,4-diamino-7-alkenylpteridines III (n = 0). The experimental process involved the reaction of 2-Aminomalononitrile 4-methylbenzenesulfonate(cas: 5098-14-6).Application of 5098-14-6

The Article related to malononitrile condensation oximinoaldehyde, aminocyanopyrazine oxide cyclization guanidine, pteridine oxide, alkenylpteridine oxide, Heterocyclic Compounds (More Than One Hetero Atom): Purines and Pteridines and other aspects.Application of 5098-14-6

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Taylor, Edward C.; Kobayashi, T. published an article in 1973, the title of the article was Pteridines. XXXII. 2-Amino-3-cyano-5-chloromethylpyrazine 1-oxide and its conversion to 6-alkenyl-substituted pteridines.Application of 5098-14-6 And the article contains the following content:

2-Amino-3-cyano-5-chloromethylpyrazine 1-oxide (I), prepared by the condensation of β-chloropyruvaldoxime with aminomalononitrile tosylate, was deoxygenated with PCl3 to 2-amino-3-cyano-5-chloromethylpyrazine (II). Both I and II were converted by conventional procedures to triphenylphosphonium ylides (Wittig reagents) and, hence, by condensation with aldehydes, to parallel series of 5-alkenylpyrazines (III and IV). Cyclization of IV with guanidine gave 2,4-diamino-6-alkenylpteridines, of interest as intermediates for the synthesis of biopterin and biopterin analogs. Some addnl. reactions of the above pyrazine intermediates are also described. The experimental process involved the reaction of 2-Aminomalononitrile 4-methylbenzenesulfonate(cas: 5098-14-6).Application of 5098-14-6

The Article related to aminocyanopyrazine conversion pteridine, pyrazine aminocyano conversion pteridine, cyanopyrazine amino conversion pteridine, alkenylpteridine, Heterocyclic Compounds (More Than One Hetero Atom): Purines and Pteridines and other aspects.Application of 5098-14-6

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Nitrile – Wikipedia,
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On December 31, 1980, Kadir, Kamaliah; Shaw, Gordon; Wright, David published an article.Application of 5098-14-6 The title of the article was Purines, pyrimidines, and imidazoles. Part 56. Some aminoimidazolecarboxamidines and derived adenines. And the article contained the following:

Cyclohexylimidazole I, prepared (37%) from H2NCH(CN)2, CH(OEt)3, and cyclohexylamine, gave 66% carboximidate II (R = OMe) on treatment with MeOH/HCl, which with NH3 gave 64% carboxamidine II (R = NH2) (III). Formylation of III gave N6-formyladenine IV (R = cyclohexyl), which was also prepared by formylation of 9-cyclohexyladenine. IV [R = CH2CH(OH)CH2OH] was similarly prepared The reaction of II (R = H) with HCO2H/Ac2O gave N6-formyladenine (IV; R = H), which was also prepared by formylation of adenine, whereas adenosine was not N-formylated under the same conditions. The experimental process involved the reaction of 2-Aminomalononitrile 4-methylbenzenesulfonate(cas: 5098-14-6).Application of 5098-14-6

The Article related to aminomalononitrile cyclocondensation, aminoimidazole, imidazole amino, carboxamidine formylation, cyclohexylimidazole, nucleoside analog adenine, Heterocyclic Compounds (More Than One Hetero Atom): Purines and Pteridines and other aspects.Application of 5098-14-6

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Nitrile – Wikipedia,
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Taylor, Edward C.; Portnoy, Robert C.; Hochstetler, Douglass C.; Kobayashi, T. published an article in 1975, the title of the article was Pteridines. XXXVIII. Synthesis of some 2,4-diamino-6-substituted methylpteridines. New route to pteroic acid.Quality Control of 2-Aminomalononitrile 4-methylbenzenesulfonate And the article contains the following content:

6-Substituted 2,4-diaminopteridines I and 6-substituted pterins II (R = Cl, OH, H, p-ClC6H4, p-EtO2CC6H4NH, PhCH2, etc.) were prepared by reaction of 2-amino-3-cyano-5-chloromethylpyrazine with nucleophiles, followed by ring closure with guanidine to give I, and final acid hydrolysis to II. The pyrazine oxides III (R = PhCH2S, p-O2NC6H4NMe, p-O2NC6H4NH) were prepared by treating XCH2COCH:NOH (X = Cl, Br) with H2NCH(CN)2.p-MeC6H4SO3H and nucleophiles. The experimental process involved the reaction of 2-Aminomalononitrile 4-methylbenzenesulfonate(cas: 5098-14-6).Quality Control of 2-Aminomalononitrile 4-methylbenzenesulfonate

The Article related to pteridine diamino, pterin, cyclization cyanoaminopyrazine guanidine, pyrazine cyclization guanidine, pyruvaldehyde oxime cyclization aminomalononitrile, Heterocyclic Compounds (More Than One Hetero Atom): Purines and Pteridines and other aspects.Quality Control of 2-Aminomalononitrile 4-methylbenzenesulfonate

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Nitrile – Wikipedia,
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Taylor, Edward C.; Berrier, John V. published an article in 1977, the title of the article was Pteridines. Part XLII. Synthesis of some benzo[g]pteridines. A novel aromatization reaction.Name: 2-Aminomalononitrile 4-methylbenzenesulfonate And the article contains the following content:

The benzopteridine I (R = NH2, R1 = R2 = H) was prepared by condensing 6-chloro-2-oximinocyclohexanone-HCl with H2NCH(CN)2.4-MeC6H4SO3H, aromatizing the quinoxaline oxide II by heating with HOAc, and condensing 2-amino-3-cyanoquinoxaline (III) with guanidine-HCl. Condensation of III with HC(OEt)3 gave I (R-R2 = H). I (R = NH2, R1 = R2 = H) was treated with HCl to give benzo[g]pterin. I [R = NH2, R1R2 = (CH)4] was obtained from 2-oximino-1-tetralone. The experimental process involved the reaction of 2-Aminomalononitrile 4-methylbenzenesulfonate(cas: 5098-14-6).Name: 2-Aminomalononitrile 4-methylbenzenesulfonate

The Article related to benzopteridine, naphthopterdine, benzopterin, pterin condensed, aromatization tetrahydroquinoxaline oxide, guanidine aminocyanoquinoxaline condensation, Heterocyclic Compounds (More Than One Hetero Atom): Purines and Pteridines and other aspects.Name: 2-Aminomalononitrile 4-methylbenzenesulfonate

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts