Synthesis and Properties of 1-Arylsulfonyl-1,2,3-triazol-5-olates

A series of 1-arylsulfonyl-4-carbamoyl-1,2,3-triazol-5-olates has been synthesized. The cyclization of diazoacetamides by the action of base has been shown to be reversible for the first time. 1-Arylsulfonyl-1,2,3-triazol-5-olates undergo rearrangement upon heating to give isomeric N-sulfonylcarbamoyldiazoacetimidolates. An equilibrium exists between these isomers in DMSO solution, which is shifted toward the acyclic derivative.     

Triple Equilibrium in N'-Aryl-N-tosyldiazomalonimidolates, 1-Tosyl-1,2,3-triazol-5-olates, and 1-Aryl-1,2,3-triazol-5-olates

A series of 1-tosyl-substituted 4-arylcarbamoyl-1,2,3-triazol-2-olates, which can undergo rearrangement to isomeric 1-aryl-4-tosylcarbamoyl-1,2,3-triazol-5-olates and N-tosyl-N'-aryldiazomalonimidolates, were synthesized. An equilibrium between these compounds is observed in solutions in DMSO. The introduction of an electron-withdrawing substituent into the aryl residue increases the stability of the 1-tosyl-1,2,3-triazoles but reduces the stability of the 1-aryl-1,2,3-triazoles. -Donating substituents increase the stability of the open-chain structure.     

Synthesis of 1-Substituted 3-Alkyl-1,2,3-triazol-3-ium-5-olates

Alkylation of 1-substituted sodium 1,2,3-triazol-5-olates with halogen derivatives occurs at the nitrogen atom in position 3 of the heteroring to give zwitterionic 1,2,3-triazol-3-ium-5-olates.     

1-Hetaryltriazenes in the synthesis of condensed mesoionic 1,2,3-triazolio-5-olates

Condensed mesoionic 1,2,3-triazoles containing an aryl or hetaryl substituent at N₍₂₎ in the ring have been synthesized by intramolecular condensation. Dedicated to Academician M. G. Voronkov on his Eighty-Fifth Birthday. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1714–1719, November, 2006.     

Synthesis and fungicidal activity of alkaloid-containing carbohydrates

N-Glycosylamines, triethylammonium salt of xylosyl-and glucosylbenzyldithiocarbamates, and their derivatives containing fragments of alkaloids were synthesized; some of these substances exhibit fungicidal activity.     

Synthesis and fungicidal activity of fluorine-containing phenylimino-thiazolidines derivatives

Nine new fluorine-containing phenylimino-thiazolidines derivatives were prepared. The structures of all compounds were confirmed by ¹H NMR, mass and high resolution mass spectroscopy. The antifungicidal activities of the title compounds on Phytophthoza capsici L., Pyriculazia ozyzae C., Fusazium spp. at 100 ppm were screened.     

Synthesis and fungicidal activity of fluorine-containing phenylimino-thiazolidines derivatives

Nine new fluorine-containing phenylimino-thiazolidines derivatives were prepared. The structures of all compounds were confirmed by NMR, mass and high resolution mass spectroscopy. The antifungicidal activities of the title compounds on Phytophthora capsici L., Pyricularia oryzae C, Fusarium spp. at 100 ppm were screened.     

几个新型呋喃氨基腈衍生物的合成及抗菌活性

用5-甲基-4-乙氧羰基呋喃氨基腈与芳醛反应制得Schiff碱,再采用NaBH4还原Schiff碱,得到3个新型5-甲基-4-乙氧羰基呋喃氨基腈衍生物.利用核磁共振谱(1H NMR)、红外光谱(IR),质谱(EI-MS)表征了产物的结构;并初步测定了产物的抗菌活性.结果表明,目标化合物的抗菌活性一般.     

Synthesis and antimicrobial activity of some new sugar-based monocyclic beta-lactams

The syntheses of some new sugar-based monocyclic beta-lactams possessing several other functionalities in addition to the carbohydrate moiety are described. The key step was the Staudinger [2+2] cycloaddition of chiral carbohydrate Schiff base 5 with phthalimidoacetyl chloride to yield the sugar-based monocyclic beta-lactam 6 as a single isomer. Treatment of protected beta-lactams 6 and 8 with methylhydrazine afforded the free amino beta-lactams 9 and 10. Acylation of these free amino beta-lactams with benzoyl, phenoxyacetyl, cinnamoyl and phenylacetyl chloride in the presence of pyridine afforded beta-lactams 11a-d and 12a-d. Some of these novel beta-lactams were found to be active against Staphilococcus citrus, Klebsiella pneumoniae, Escherichia coli and Bacillus subtilis.     

Synthesis and systemic fungicidal activity of silicon-containing azole derivatives

A new series of azole derivatives containing silicon were synthesized and evaluated for fungicidal activity against rice sheath blight by submerged application. Among them, 2-(4-fluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-3-trimethylsilylpr opan-2-ol (9a) exhibited satisfactory efficacy at 12.5 grams per 10 ares.     

含1,3,4-(口恶)二唑取代的酰基硫脲的合成及杀菌活性

大量文献报道了1,3,4-(口恶)二唑的合成及广泛的生物活性[1-3],酰基硫脲类化合物也因其广谱的生物活性引起了人们浓厚的研究兴趣[4-5].根据活性因子叠加的原理,本文将一系列1,3,4-(口恶)二唑引入到酰基硫脲中,从对氯苯氧乙酸出发,得到的酰基异硫氰酸酯再与一系列2-氨基-5-芳基-1,3,4-(口恶)二唑反应,合成了10个酰基硫脲类化合物.所有化合物均经元素分析、红外光谱、核磁共振谱和质谱确认.同时对所有化合物进行了生物活性测试.合成路线如下.     

4-Aryl(benzyl)sulfonyl-2-chloro-5-polyfluoroalkyl-1,2,3-triazoles. The first monocyclic N-chloro-1,2,3-triazoles

Treatment of 4-aryl(benzyl)sulfonyl-5-polyfluoroalkyl-v-triazoles with NaOCl gave the 4-aryl(benzyl)-sulfonyl-2-chloro-5-polyfluoroalkyl-v-triazole derivatives which contain a chlorine atom only on the N₍₂₎ atom of the heterocycle. The structure of 2-chloro-5-(1,1,2,2,3,3-hexafluoropropyl)-4-(p-tolyl-sulfonyl)-2H-[1,2,3]triazole has been established by X-ray structural investigation. The presence of a highly polarized N—Cl bond with a positive halogen atom causes the N-chlorotriazoles to react with KCN and KF as strong acids to form the potassium salts of the triazoles and to form 4-arylsulfonyl-2-(2-chloro-1-ethoxyethyl)-5-polyfluoroalkyl-2H-[1,2,3]triazoles with vinyl ethyl ether. It was found that chlorination of 4-arylsulfonyl-5-polyfluoroalkyl-v-triazoles in the presence of KF gives 4-chloro-5-polyfluoroalkyl-2H-[1,2,3]triazoles. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1342–1352, September, 2007.     

Synthesis and fungicidal activity of novel 3,5-diarylpyrazole derivatives

(E)-3-(2-chlorophenyl)-1-(2,4-dichlorophenyl) prop-2-en-1-one was prepared from 2-chlorobenzaldehyde followed by cyclization with hydrazine monohydrate. Eight new 3-(2,4-Di-chlorophenyl)-5-(2-chlorophenyl)-4,5-dihydro-N-acylpyrazole derivatives were synthesized and characterized by elemental analysis, IR and ¹H NMR spectroscopy. The experimental results show that the inhibition ratio of compounds 3f towards H. Oryzae and P. oryzae at 50 mg·L⁻¹ is 55.2% and 57.1%, respectively. The inhibition ratio of compounds 3g towards H. Oryzae, P. oryza, S. Sclerotiorum at 50 mg·L⁻¹ is 53.3%, 60.0%, 50.4% respectively. __________ Translated from Chinese Journal of Applied Chemistry, 2007, 27(7): 835–837     

含1，3，4-噁二唑取代的酰基硫脲的合成及杀菌活性

大量文献报道了1，3，4-噁二唑的合成及广泛的生物活性，酰基硫脲类化合物也因其广谱的生物活性引起了人们浓厚的研究兴趣。根据活性因子叠加的原理，本文将一系列1，3，4-噁二唑引入到酰基硫脲中，从对氯苯氧乙酸出发，得到的酰基异硫氰酸酯再与一系列2-氨基-5-芳基-1，3，4-噁二唑反应，合成了10个酰基硫脲类化合物。所有化合物均经元素分析、红外光谱、核磁共振谱和质谱确认。同时对所有化合物进行了生物活性测试。合成路线如下。     

Synthesis of 5-amino-1,2,3-thiadiazole

A convenient method is proposed for the synthesis of ethyl phthalimidoethylideneaminocarbamate, an intermediate in the synthesis of 5-amino-1,2,3-thiadiazole.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 112–113, January, 1989.     

Synthesis and fungicidal activity of methylsulfanylmethyl ether derivatives of levoglucosenone

Chemistry of Heterocyclic Compounds - A series of derivatives were synthesized on the basis of levoglucosenone that contained hydroxy groups at the С-4 atom or С-2 and С-4 atoms...     

Synthesis and fungicidal activity of S-amino derivatives of O-alkyldithiocarbonic acids

S-Amino derivatives of O-alkyldithiocarbonic acid were prepared by oxidative condensation of certain alkaloids with sodium xanthates. Some of the compounds synthesized exhibit fungicidal activity.