scholarly journals EFFECT OF STRUCTURE OF ALKYL SUBSTITUENT AT N(2) POSITION OF HETEROCYLE ON NUCLEOPHILIC SUBSTITUTION OF O-NUCLEOPHILES FOR NITRO GROUP IN N-SUBSTITUTED 3-NITRO-1,2,4-TRIAZOLES

2021 ◽  
pp. 3-7
Author(s):  
И.А. Крупнова ◽  
Г.Т. Суханов ◽  
А.Г. Суханова ◽  
К.К. Босов ◽  
Ю.В. Филиппова ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Nitro Group ◽  
Alkyl Substituent ◽  
Derivatives Of ◽  
By Products ◽  
Methoxide Anion ◽  
Effect Of Structure

Проведены исследования процесса SNipso–замещения нитрогруппы алкилзамещенных производных 3-нитро-1,2,4-триазола. Показано, что N(2)-изомерные производные нитротриазолы вступают в реакцию нуклеофильного замещения нитрогруппы с метоксид-анионом с образованием соответствующих метокси-производных. Реакции SNipso–замещения нитрогруппы 1-алкил-5-нитро-1,2,4-триазолов метоксид-анионом практически селективны. Доля побочных продуктов не превышает 1,0 %. Here we investigate the SNipso–substitution of the nitro group in alkyl-substituted derivatives of 3-nitro-1,2,4-triazole. The N(2)-isomeric derivatives of nitrotriazoles were found to engaged in the reaction of nucleophilic substitution of the nitro group with the methoxide anion to furnish the respective methoxy derivatives. The reactions of SNipso–substitution of the nitro group in 1-alkyl-5-nitro-1,2,4-triazoles with the methoxide anion were almost selective. The portion of by-products was not in excess of 1.0 %.

Infrared spectra and substituent effects in 2-(3-, and 4-substituted phenylmethylene)-1,3-cycloheptanediones

1983 ◽  
Vol 48 (2) ◽  
pp. 586-595 ◽  
Author(s):  
Alexander Perjéssy ◽  
Pavol Hrnčiar ◽  
Ján Šraga
Keyword(s):  
Substituent Effects ◽  
Phenyl Group ◽  
Wave Number ◽  
Vibrational Coupling ◽  
Wave Numbers ◽  
Stretching Vibration ◽  
Stretching Vibrations ◽  
The Relationship ◽  
Derivatives Of ◽  
Effect Of Structure

The wave numbers of the fundamental C=O and C=C stretching vibrations, as well as that of the first overtone of C=O stretching vibration of 2-(3-, and 4-substituted phenylmethylene)-1,3-cycloheptanediones and 1,3-cycloheptanedione were measured in tetrachloromethane and chloroform. The spectral data were correlated with σ+ constants of substituents attached to phenyl group and with wave number shifts of the C=O stretching vibration of substituted acetophenones. The slope of the linear dependence ν vs ν+ of the C=C stretching vibration of the ethylenic group was found to be more than two times higher than that of the analogous correlation of the C=O stretching vibration. Positive values of anharmonicity for asymmetric C=O stretching vibration can be considered as an evidence of the vibrational coupling in a cyclic 1,3-dicarbonyl system similarly, as with derivatives of 1,3-indanedione. The relationship between the wave numbers of the symmetric and asymmetric C=O stretching vibrations indicates that the effect of structure upon both vibrations is symmetric. The vibrational coupling in 1,3-cycloheptanediones and the application of Seth-Paul-Van-Duyse equation is discussed in relation to analogous results obtained for other cyclic 1,3-dicarbonyl compounds.

Preparation of Chloro and Sulfanyl Derivatives of 1-(2-Deoxy-4-C-hydroxymethyl-α-L-threo-Pentofuranosyl)uracil

1997 ◽  
Vol 62 (7) ◽  
pp. 1114-1127 ◽  
Author(s):  
Hubert Hřebabecký ◽  
Jan Balzarini ◽  
Antonín Holý
Keyword(s):  
Nucleophilic Substitution ◽  
Hydrogen Chloride ◽  
Thionyl Chloride ◽  
Sodium Methoxide ◽  
Thioacetic Acid ◽  
Uracil Derivatives ◽  
Derivatives Of ◽  
Hiv 1

3'-Chloro and 3'-acetylsulfanyl derivatives of 1-(2-deoxy-4-C-hydroxymethyl-α-L-threo-pentofuranosyl)uracil were prepared by reaction of 2,3'-anhydro-1-{5'-O-benzoyl-4'-C-[(benzoyloxy)methyl]-2'-deoxy-α-L-erythro-pentofuranosyl}uracil (3) with hydrogen chloride and thioacetic acid, respectively. The reaction with hydrogen chloride gave a mixture of N-1 and N-3 substituted uracil derivatives 12 and 14. Reaction of 1-{3-O-benzoyl-4-C-[(benzoyloxy)methyl]-2-deoxy-α-L-threo-pentofuranosyl}uracil (7) with thionyl chloride and subsequent debenzoylation afforded 1-(4-C-chloromethyl-2-deoxy-β-D-erythro-pentofuranosyl)uracil (19). Nucleophilic substitution with lithium thioacetate, followed by deacylation, converted 1-{3-O-benzoyl-4-C-[(benzoyloxy)methyl]-2-deoxy-5-O-p-toluenesulfonyl-α-L-threo-pentofuranosyl}uracil (9) into 1-(2-deoxy-4-C-sulfanylmethyl-β-D-erythro-pentofuranosyl)uracil (21). The obtained thiols were oxidized with iodine or air to give 1,1'-[disulfandiylbis(2,3-dideoxy-4-hydroxymethyl-α-L-threo-pentofuranose-3,1-diyl]di(pyrimidine-2,4-(1H,3H)-dione) (17) and 1,1'-[disulfandiylbis(2,5-dideoxy-4-hydroxymethyl-α-L-threo-pentofuranose-5,1-diyl]di(pyrimidine-2,4(1H,3H)-dione) (22). Reaction of 1-{3-acetylsulfanyl-5-O-methanesulfonyl-4-C-[(benzoyloxy)methyl]-2,3-dideoxy-α-L-threo-pentofuranosyl)}uracil (24) with methanolic sodium methoxide afforded 1-(3,5-anhydro-2,3-dideoxy-4-C-hydroxymethyl-3-sulfanyl-α-L-threo-pentofuranosyl)uracil (25). The same reagent was used in the preparation of 1-(3,5-anhydro-2-deoxy-4-C-hydroxymethyl-α-L-threo-pentofuranosyl)uracil (26) from 1-{4-C-[(benzoyloxy)methyl]-2-deoxy-5-O-p-toluenesulfonyl-α-L-threo-pentofuranosyl}uracil (8). From the series of 4'-substituted 2'-deoxyuridine derivatives, synthesized in this study, solely the 4'-chloromethyl derivative 19 and the oxetane derivative 26 exhibited an appreciable activity against HIV-1 and HIV-2.

Heterocyclic derivatives of purines. 5. Nucleophilic substitution in series of imidazo[1,2-f]purine derivatives

1984 ◽  
Vol 20 (3) ◽  
pp. 330-334
Author(s):  
S. N. Garmash ◽  
B. A. Priimenko ◽  
N. A. Klyuev ◽  
N. I. Romanenko ◽  
A. K. Sheinkman
Keyword(s):  
Nucleophilic Substitution ◽  
Purine Derivatives ◽  
Heterocyclic Derivatives ◽  
In Series ◽  
Derivatives Of

Vicarious nucleophilic amination of nitroquinolines with 4-amino-1,2,4-triazole

2008 ◽  
Vol 86 (7) ◽  
pp. 682-685 ◽  
Author(s):  
Barbara Szpakiewicz ◽  
Maria Grzegożek
Keyword(s):  
Dimethyl Sulfoxide ◽  
Nucleophilic Substitution ◽  
Nitro Group ◽  
Para Position ◽  
Basic Medium ◽  
Ortho Position ◽  
Vicarious Nucleophilic Substitution

3-, 5-, 6-, 7- and 8-Nitroquinolines react with 4-amino-1,2,4-triazole in basic medium (potassium tert-butoxide-dimethyl sulfoxide) giving amino products of the vicarious nucleophilic substitution (VNS) of hydrogen, predominantly at ortho position to the nitro group, except 8-nitroquinoline, which reacts at para position. Additionally, furazano[3,4-f]- and furazano[3,4-h]quinoline were obtained in the case of 5- and 8- nitroquinoline, respectively. 2-Nitroquinoline was aminated to 2-quinolino(1,2,4-triazol-4-yl)amine in these conditions.Key words: nitroquinolines, vicarious nucleophilic substitution (VNS), 4-amino-1,2,4-triazole.

scholarly journals The features of nucleophilic substitution of the nitro group in 4-alkyl-6-nitro-1,2,4-triazolo[5,1-c][1,2,4]triazines

2017 ◽  
Vol 4 (1) ◽  
pp. 11-24
Author(s):  
E. N. Ulomsky ◽  
D. N. Lyapustin ◽  
V. V. Fedotov ◽  
O. S. El'tsov ◽  
I. M. Sapozhnikova ◽  
...  
Keyword(s):  
Nucleophilic Substitution ◽  
Nitro Group
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