ChemInform Abstract: sym‐Triazines. Part 8. Synthesis and Some Reactions of 4,6‐Disubstituted 2‐(1H‐Pyrrolyl)‐1,3,5‐triazines.

Chesnyuk, A. A.; Mikhailichenko, S. N.; Zaplishnyi, V. N.; Konyushkin, L. D.; Фирганг, С. И.

doi:10.1002/chin.200921169

ChemInform

2009

DOI: 10.1002/chin.200921169

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ChemInform Abstract: sym‐Triazines. Part 8. Synthesis and Some Reactions of 4,6‐Disubstituted 2‐(1H‐Pyrrolyl)‐1,3,5‐triazines.

A. A. Chesnyuk

S. N. Mikhailichenko

V. N. Zaplishnyi

et al.

Abstract: Triazine derivatives R 0655 sym-Triazines. Part 8. Synthesis and Some Reactions of 4,6-Disubstituted 2-(1H-Pyrrolyl)-1,3,5-triazines. -A series of sym-triazine derivatives containing pyrrole, triazole or iminophosphorane fragments with high bioactivity potential are synthesized for the first time. -(CHESNYUK, A. A.; MIKHAILICHENKO, S. N.; ZAPLISHNYI, V. N.; KONYUSHKIN, L. D.; FIRGANG, S. I.; Chem. Heterocycl.

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“…In a series of 1,3,5-triazine derivatives, an example of such a synthesis was described for 1,3,5-triazinecarbonitriles [5]. In contrast to the reaction of nitriles with hydroxylamine [5], the method for synthesizing of 1,3,5-triazinylamidoximes using 1,3,5-triazinylnitroformaldoximes as starting materials is more general since it permits the preparation of amidoximes substituted at the amino group. The reaction of nitroformaldoximes 1a-d with ammonia and various amines in ethanol at 20-25°C gives 1,3,5-triazinylamidoximes 3a-h.…”

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confidence: 98%

Reactions of 1,3,5-triazinylnitroformaldoxime 4.* synthesis of (5-R-1,2,4-oxadiazol-3-yl)-1,3,5-triazines

Бахарев

Гидаспов

Selezneva

et al. 2012

Chem Heterocycl Comp

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The [3+2] cycloaddition of nitrile oxides to nitriles is one of the most commonly used methods for the synthesis of 1,2,4-oxadiazoles [2,3]. In previous work [1], we have developed a synthesis of the 3,5-disubstituted isoxazoles using the reaction of acetylenes with 1,3,5-triazinylnitrile oxides generated by the thermolysis of the corresponding 1,3,5-triazin-6-ylnitroformaldoximes. In the present work, we have studied the possibility of obtaining (5-R-1,2,4-oxadiazol-3-yl)-1,3,5-triazines using the analogous [3+2] cycloaddition reactions of 1,3,5-triazinylnitrile oxides to nitriles. The reaction was carried out by heating a solution or suspension of nitroformaldoximes 1a-d in various nitriles. Formation of nitrogen oxides was observed upon heating, indicating the release of nitrous acid and the formation of nitrile oxides. However, at the end of the reaction as indicated by thin-layer chromatographic monitoring of the starting compounds 1a-d, 3,4-di-(4-R-6-methoxy-1,3,5-triazin-2-yl)-furoxanes 2a-d were isolated instead of the expected 2-R-4-methoxy-6-(5-R-1,2,4-oxadiazol-3-yl)-1,3,5-triazines (Scheme 1).Thus, under the conditions described above, nitrile does not participate in the reaction but rather acts as a solvent. Therefore, dimerization of the intermediate nitrile oxides occurs to give furoxanes 2a-d exclusively analogous to the process described in our previous work [4] instead of formation of (5-R-1,2,4-oxadiazol-3-yl)-1,3,5-triazines.

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confidence: 98%

Reactions of 1,3,5-triazinylnitroformaldoxime 4.* synthesis of (5-R-1,2,4-oxadiazol-3-yl)-1,3,5-triazines

Бахарев

Гидаспов

Selezneva

et al. 2012

Chem Heterocycl Comp

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“…The reaction of the dioxime 86 with K 3 Fe(CN) 6 in aqueous alkali gives furoxano [3,4-b]piperazines 87 with yields of 72-98% [114]. The O-acylated 1,2,4-triazine [115,116] and 1,3,5-triazine [34] amidoximes are easily transformed into 1,2,4-oxadiazole derivatives of triazines. 1,3,4-Thiadiazine oximes in a basic medium [46] and 1,2,6-thiadiazine oximes in an acidic medium [72] are converted into thiadiazoles.…”

mentioning

confidence: 98%

“…Na 2 CO 3 or + O-Acylated 1,3,5-triazine oximes were obtained from the corresponding oximes and chlorides [34] or acid anhydrides [35,36].…”

mentioning

confidence: 99%

Oximes of six-membered heterocyclic compounds with two and three heteroatoms. II.* Reactions and biological activity (review)

Абеле

Golomba

et al. 2010

Chem Heterocycl Comp

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Data on the reactions of pyridazine, pyrimidine, pyrazine, triazine, oxazine, thiazine, oxadiazine, and thiadiazine aldoximes, ketoximes, and amidoximes and their derivatives are reviewed. The synthesis of new heterocycles based on the oximes of six-membered heterocyclic compounds with two and three heteroatoms is considered separately. The principal results of research into the biological activity of these oximes and their ethers are also presented.The oximes of six-membered heterocyclic compounds with two and three heteroatoms are widely used as intermediates in fine organic synthesis. Their production methods and structural features were examined in the review [1]. In this article we discuss the reactions of pyridazine, pyrimidine, pyrazine, triazine, oxazine, thiazine, oxadiazine, and thiadiazine aldoximes, ketoximes, and amidoximes and their derivatives. Methods for the synthesis of new heterocyclic systems from the derivatives of these oximes are considered in a separate section. In the last section some results from investigation of the biological activity of the ethers of these oximes are considered.

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“…Nitriles are widely used in the synthesis of compounds belonging to various classes, including heterocyclic compounds [5]. In the present work the cyano group in III was used to build up 1,2,4-oxadiazole ring according to [6], through intermediate amide oxime IV and its O-acyl derivatives.…”

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confidence: 99%

Synthesis of 3-substitued 5-(2-thienyl)isoxazoles

2011

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The reaction of 3,4,4-trichloro-1-(2-thienyl)but-3-en-1-one with hydroxylamine gave 3-hydroxyiminomethyl-5-(2-thienyl)isoxazole which was converted into 5-(2-thienyl)isoxazole-3-carbonitrile by the action of acetic anhydride in pyridine. 5-(2-Thienyl)isoxazole-3-carbonitrile reacted with hydroxylamine to produce the corresponding amide oxime. Heterocyclization of its O-acyl derivatives in acetic acid afforded 5-substituted 3-[5-(2-thienyl)isoxazol-3-yl]-1,2,4-oxadiazoles.Functionally substituted isoxazoles and thiophenes exhibit a broad spectrum of biological activity and are used as medicines and chemical means for plant protection [1]. Combination of both isoxazole and thiophene rings in a single molecule makes such compounds attractive from the viewpoint of their biological properties, and the presence of reactive substituents provides the possibility for subsequent functionalization and purposeful synthesis of useful products.We recently reported on a convenient synthesis of 3,4,4-trichloro-1-(2-thienyl)but-3-en-1-one (I, 2-thienyl trichloroallyl ketone) from accessible 3,4,4-trichlorobut-3-enoic acid [2] and showed that compound I may be regarded as synthetic equivalent of β-chlorovinyl ketones; reaction of the latter with hydroxylamine underlies a classical procedure for the synthesis of isoxazoles [3].The goal of the present work was to synthesize 5-(2-thienyl)isoxazoles containing various functional groups in position 3 of the isoxazole ring on the basis of thienyl trichloroallyl ketone I. The reaction of ketone I with hydroxylamine in boiling methanol involved the carbonyl group and internal chlorine atom and was accompanied by heterocyclization to produce isoxazole ring. 3-Dichloromethyl-5-(2-thienyl)isoxazole (IIa) thus formed reacted with the second hydroxylamine molecule at the dichloromethyl group to give 3-hydroxyiminomethyl-5-(2-thienyl)isoxazole (II) in 89% yield. Unlike the reaction of hydroxylamine with aryl trichloroallyl ketones [4], we failed to isolate intermediate dichloromethyl-substituted isoxazole IIa. Even under mild conditions and in the presence of excess compound I, the only product was oxime II (Scheme 1).Compound II was identified by IR, 1 H NMR, and mass spectra and elemental analysis. In the IR spectrum of II, stretching vibrations of the C=C and C=N bonds gave rise to absorption bands at 1500, 1523, and 1599 cm -1 , and a broad absorption band centered at 3230 cm -1 was assigned to H-bonded hydroxy group. The 1 H NMR spectrum of II contained singlets from the CH proton in the isoxazole ring (δ 6.88 ppm), exocyclic =CH proton (δ 8.18 ppm), and hydroxy proton (δ 11.19 ppm). Protons in the thiophene ring resonated as a multiplet at δ 7.21 ppm and two doublets at δ 7.68 and 7.72 ppm. Compound II displayed in the 13 C NMR spectrum signals from C 4 H in the isoxazole ring (δ C 96.08 ppm), CH carbon atoms in the thiophene ring (δ C 127.92, 128.48, and 129.01 ppm), exocyclic CH=N carbon atom (δ C 139.52 ppm), and three quaternary carbon atoms (δ C 135.75, 159.46, and 165.23 ppm). The ...

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ChemInform Abstract: sym‐Triazines. Part 8. Synthesis and Some Reactions of 4,6‐Disubstituted 2‐(1H‐Pyrrolyl)‐1,3,5‐triazines.

Cited by 3 publications

References 1 publication

Reactions of 1,3,5-triazinylnitroformaldoxime 4.* synthesis of (5-R-1,2,4-oxadiazol-3-yl)-1,3,5-triazines

Reactions of 1,3,5-triazinylnitroformaldoxime 4.* synthesis of (5-R-1,2,4-oxadiazol-3-yl)-1,3,5-triazines

Oximes of six-membered heterocyclic compounds with two and three heteroatoms. II.* Reactions and biological activity (review)

Synthesis of 3-substitued 5-(2-thienyl)isoxazoles

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