- On triazoles. XXXIV. The correct structure of the ethoxycarboxylated 5-amino-1H-1,2,4-triazole and its product with hydrazine
-
The structure of the ethoxycarboxylated product of 5-amino-1H-1,2,4-triazole and its hydrazide was corrected using their ir, pmr, cmr and mass spectra.
- Reiter
-
-
Read Online
- Design and synthesis of novel cylopentapyrazoles bearing 1,2,3-thiadiazole moiety as potent antifungal agents
-
In drug-resistant phytopathogenic fungi, there has been extensive research on microbiological and antifungal drug development. In this study, a novel series of cylopentapyrazole bearing a 1,2,3-thiadiazole ring 2a-e were designed and synthesized according to the principle of combination of bioactive structures. Thus, we have employed a [3 + 2] cycloaddition with 4-methyl-[1,2,3] thiadiazole-5-carboxylic acid hydrazones 1a-e and cyclopentadiene ring. Novel synthesized compounds were identified with IR, 1H and 13C NMR, mass spectrometry and elemental analysis then, antifungal activities were assayed. Based on our study, a combination of the compounds 1a and 2b possess remarkable antifungal activity against Botrytis cinerea AHU 9424 with 100% inhibition. EC50 values were calculated by studying different doses in combinations with high inhibition rates. The combination of 1a + 2b has an EC50 value at 6.37 and 13.85 μg/ml concentrations against B. cinerea and F. culmorum, respectively. The combination of compound 1a + 2b, having a cylopentapyrazole ring on the 1,2,3-thiadiazole backbone, shows promising fungicidal activity and deserves further development. Additionally, the homology model of the CYP51 enzyme that belongs to Fusarium moniliforme was generated using CYP51B (PDB ID: 6CR2), and molecular docking was performed using this homology model for each compound. The results of this study clearly indicate that these novel compounds can be identified as promising lead compounds and potential fungicidal agents in future.
- Giray, Betül,Karada?, Ay?e Esra,?pek, ?zgecan ?avlu?,Pekel, Hanife,Güzel, Mustafa,Kü?ük, Hatice Ba?p?nar
-
supporting information
(2019/12/30)
-
- A METHOD FOR PRODUCING POTASSIUM 1,1 -DINITRAMINO-5,5-BISTETRAZOLATE AND EXPLOSIVE COMPOSITIONS COMPRISING SAID SALT
-
A method of producing K2DNABT wherein a biztetrazole intermediate is nitrated using a nitrating agent selected from the following: dinitronium disulphate; a mixture of nitric acid and sulfuric acid; a mixture of nitric acid and phosphorous pentoxide; and nitric acid with acetic anhydride.
- -
-
Paragraph 0051; 0110
(2020/06/16)
-
- Palladium-Catalyzed Oxidative C–H Alkoxycarbonylation of Arenes with Alkylcarbazates Directed by N-Heterocyclic Substituents
-
With alkyl carbazates as the green ester source, a novel palladium-catalyzed oxidative free radical carbonylative transformation of the C–H bond on aromatic rings to produce esters has been developed. Good yields of the corresponding products have been obtained with wide functional group tolerance and excellent regioselectivity. A variety of alkyl carbazates are found to be suitable reactants for the ortho-alkoxycarbonylation on the aromatic ring.
- Yogesh Kumar, Gujjenahalli Ramalingaiah,Begum, Noor Shahina
-
supporting information
p. 4698 - 4704
(2020/07/04)
-
- 1. 2, 3 - thiadiazole - 5 - a amidine compound synthesis method
-
The invention discloses a novel method for synthesizing a 1,2,3-thiadiazole-5-formamidine compound. The target compound shown in general formula TDCA is prepared from a compound as shown in general formula M by virtue of a methylation reaction. The target component as shown in the general formula M is prepared from a compound as shown in general formula A and a compound as shown in general formula N by virtue of a condensation reaction, wherein during the methylation reaction, preferably, a catalyst is an organic metallic catalyst consisting of cuprous iodide and a ligand, namely 2,2,6,6-tetramethyl-3,5-heptadione; during the reaction, preferably, dimethylbenzene is taken as a solvent, and the optimum reaction temperature is 100-140 DEG C. The method disclosed by the invention is high in yield and more environment-friendly (as shown in Specification).
- -
-
Paragraph 0025; 0046; 0047
(2017/06/13)
-
- guan Huanfa synthetic multi-nitrogen heterocyclic ring sai oxadiazole - 5 - a amidine compounds
-
The invention discloses an N-trisubstituted-1,2,3-thiadiazoles-5-formamidine target compound of which the general formula is TDCA. The N-trisubstituted-1,2,3-thiadiazoles-5-formamidine target compound is obtained from an M compound through a cyclization reaction. The new synthetizing method is high in yield, catalysts are easy to prepare, the catalysts are low in cost, phosphoric waste water is less, and the multi-nitrogen heterocycle thiadiazoles-5-formamidine compound is environment-friendly. (As shown in the Description).
- -
-
Paragraph 0043-0044
(2017/07/21)
-
- Three nitrogen heterocycle containing 1, 2, 3 - thiadiazole - 5 - a amidine compounds and synthesis
-
The invention discloses an N-trisubstituted-1,2,3-thiadiazole-5-formamidine compound with three aromatic rings of general formula TDCA and a synthesis method of N-trisubstituted-1,2,3-thiadiazole-5-formamidine compound. The target compound of general formula TDCA is obtained by reacting a compound of general formula B and a compound of general formula A, wherein references of X and Y in the general formula A are the same as those in the general formula TDCA.
- -
-
Paragraph 0059; 0061; 0062
(2017/08/25)
-
- Synthesis, Crystal Structure, and Biological Activity of Some Novel Sulfoxide Compounds Containing 1,2,3-Thiadiazole Moiety
-
Some new sulfoxide compounds containing 1,2,3-thiadiazole moiety were synthesized from diethyl carbonate and hydrazine hydrate by multi-step reactions. Their structures were confirmed by NMR, MS, and elemental analysis. One of the title compounds, 5-(4-cyclopropyl-5-((3-fluorobenzyl)sulfinyl)-4H-1,2,4-triazol-3-yl)-4-methyl-1,2,3-thiadiazole (C15H14FN5OS2), was structurally determined by a single crystal X-ray diffraction study. The biological activity of the title compound was determined, and the results showed that it displays moderate biological activities.
- Min, Li-Jing,Yang, Ming-Yan,Mu, Jin-Xia,Sun, Zhao-Hui,Tan, Cheng-Xia,Weng, Jian-Quan,Liu, Xing-Hai,Zhang, Yong-Gang
-
p. 1884 - 1892
(2015/12/12)
-
- Synthesis and biological activity of acylthiourea derivatives contain 1,2,3-thiadiazole and 1,3,4-thiadiazole
-
In order to investigate the biological activity of novel thiourea compounds, some novel 1,2,3-thiadiazole derivatives containing 1,3,4-thiadiazole were synthesized under phase transfer catalyzed condition(PEG-600)by multi-step reactions. The chemical structures of all compounds were established by 1H NMR, FTIR, MS, and elemental analysis, and some of these compounds were investigated for fungicidal activity and plant growth regulatory activity. The bioassay results indicated that some of these compound exhibited moderate activities.
- Yang, Ming-Yan,Zhao, Wen,Sun, Zhao-Hui,Tan, Cheng-Xia,Weng, Jian-Quan,Liu, Xing-Hai
-
p. 314 - 318
(2015/04/14)
-
- Synthesis and antifungal activity of 1,2,3-thiadiazole derivatives containing 1,3,4-thiadiazole moiety
-
A series of 4-methyl-N-(5-substituted-1 3,4-thiadiazol-2-yl)-1,2,3- thiadiazole-5-carboxamide 6a~6j. The chemical structures were confirmed by 1H NMR, FTIR, MS, and elemental analysis. All the compounds were investigated for antifungal activity. The antifungal activity results indicated that compound 6a exhibited good activities against C. arachidicola. It can be compared with the commercial drug. The compounds 6e, 6f, 6i, 6j exhibited moderate activity.
- Yan, Shui-Lin,Yang, Ming-Yan,Sun, Zhao-Hui,Min, Li-Jing,Tan, Cheng-Xia,Weng, Jian-Quan,Wu, Hong-Ke,Liu, Xing-Hai
-
p. 940 - 943
(2014/07/21)
-
- Synthesis and antifungal activity of novel 1,2,4-triazole derivatives containing 1,2,3-thiadiazole moiety
-
Starting from carbonic acid diethyl ester, a series of 1,2,4-triazole derivatives containing 1,2,3-thiadiazole were synthesized. Reactions were performed by microwave irradiation or ultrasonic irradiation as well as by conventional heating. The structure of title compounds was characterized by 1H-NMR, MS, and elemental analyses. The fungicidal activities of these compounds were tested in vivo. Most of title compounds exhibited good antifungal activity against Pseudoperonospora cubensis. Some of title compounds displayed moderate antifungal activities against Fusarium oxysporum, Pseudoperonospora cubensis, Sphaerotheca fuligenea, Corynespora cassiicola, and Xanthomonas axonopodis.
- Tan, Cheng-Xia,Shi, Yan-Xia,Weng, Jian-Quan,Liu, Xing-Hai,Zhao, Wei-Guang,Li, Bao-Ju
-
p. 690 - 694
(2014/06/10)
-
- Synthesis and bioactivities of novel 1,3,4-oxadiazole derivatives containing 1,2,3-thiadiazole moiety
-
Some novel 1,3,4-oxadiazole derivatives containing 1,2,3-thiadiazole were synthesized under microwave-assistant condition by multi-step reactions. The structures were characterized by 1H NMR, MS, and elemental analyses. The target compounds were evaluated for their herbicidal activities against Brassica campestris and Echinochloa crusgalli, and the results indicated that some of the title compounds displayed good herbicidal activities.
- Sun, Guo-Xiang,Yang, Ming-Yan,Sun, Zhao-Hui,Wu, Hong-Ke,Liu, Xing-Hai,Wei, Yun-Yang
-
p. 1895 - 1900
(2015/10/29)
-
- Synthesis and biological evaluation of novel n-[(7-pyridin-4-yl-2, 3-dihydro-benzofuran-2-yl) methyl]-(4-methyl-1, 2, 3-thiadiazole-5-yl) formamide as a potent immunosuppressant agent
-
N-[(7-pyridin-4-yl-2, 3-dihydro-benzofuran-2-yl) methyl]-(4-methyl-1, 2, 3-thiadiazole-5-yl)-Formamide (1) was synthesized and its immunosuppressive activity was evaluated. The results showed it had highly immunosuppressive activity and can be studied as lead compound in the development of immunosuppressant agent.
- Fan, Chen,Wang, Yubin,Lu, Peng,Xue, Xiaojian,She, Jinxiong
-
p. 375 - 379
(2014/03/21)
-
- Synthesis, crystal structure, and biological activity of a novel 1,2,3-thiadiazole compound containing 1,2,4-triazole moiety
-
A new 1,2,3-thiadiazole compound containing 1,2,4-triazole moiety, C1 5H14FN5 O2S2, has been synthesized and the crystal structure was determined by single crystal X-ray diffraction study. The biological activity of the title compound was determined and the results showed that title compounds 10 showed higher inhibition abilities of rape root than the control cyclopropane-1,1-dicarboxylic acid at 100 μg/mL (73%) and weak activity against Echinochloa crusgalli (28%) and KARI (35%) at 100 μg/mL. [Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements for the following free supplemental files: additional text, figures, tables.]
- Min, Li-Jing,Tan, Cheng-Xia,Weng, Jian-Quan,Liu, Xing-Hai
-
p. 379 - 386
(2014/03/21)
-
- Phase transfer catalyzed synthesis and biological activity of thiourea derivatives containing 1,2,3-thiadiazole moiety
-
A series of N-(substituted-phenyl)-N′-(4-methyl-1,2,3-thiadiazole-5-yl)-thiourea (7a-7e) were synthesized and characterized. The chemical structures of all the compounds were confirmed by 1H NMR, MS and elemental analysis. All the compounds were investigated for fungicidal activity and plant growth regulatory activity. The bioassay results indicated that some of these compound exhibit moderate fungicidal activities.
- Min, Li-Jing,Yang, Ming-Yan,Sun, Zhao-Hui,Tan, Cheng-Xia,Weng, Jian-Quan,Wu, Hong-Ke,Liu, Xing-Hai
-
p. 7413 - 7415
(2015/04/22)
-
- Synthesis and crystal structure of novel ethyl 2-chloro-2-(4-(p-tolyl)-1,2, 3-thiadiazol-5-yl)acetate
-
A new 1,2,3-thiadiazole compound was synthesized. The crystal structure of the title compound (C13H13ClN2O2S, Mr = 296.76) has been determined by single-crystal X-ray diffraction. The crystal is of triclinic, space group P-1 with a = 6.903(2), b = 9.875(3), c = 10.903(4) A, α = 75.217(5) °, β = 79.698(5) °, γ = 80.788(5)°, V = 701.9(4)A3, Z = 2, F(000) = 308, Dc = 1.404 g/cm3, μ = 0.42 mm-1, the final R1 = 0.0324 and wR2 = 0.0823 for 2349 observed reflections with I > 2σ(I). A total of 4068 reflections were collected, of which 2842 were independent (Rint = 0.0146).
- Jin, Jian-Chang,Sun, Zhao-Hui,Yang, Ming-Yan,Sun, Na-Bo,Jin, Jian-Zhong,Wu, Hong-Ke
-
p. 1408 - 1411
(2014/01/06)
-
- Synthesis, crystal structure and biological activity of a novel 1,2,3-thidiazole compound
-
A new 1,2,3-thiadiazole compound was synthesized and characterized by 1H NMR, MS and HRMS. The crystal structure of the title compound (C12H11ClN2O4S2, Mr = 346.80) has been determined by single-crystal X-ray diffraction. The crystal is of triclinic, space group P-1 with a = 8.4425(17) A, b = 8.9801(18) A, c = 9.859(2) A, α = 84.36(3) °, β = 86.71(3)°, γ = 83.25(3)°, V = 737.9(3)A3, Z = 2, F(000) = 356, Dc = 1.561 g/cm3, μ = 0.557 mm-1, the final R1 = 0.0380 and wR2 = 0.0982 for 2160 observed reflections with I > 2σ(I). A total of 12585 reflections were collected, of which 2601 were independent (Rint = 0.0364). The herbicidal activity of title compound was determined, the results showed the title compound displayed excellent herbicidal activity against Brassica campestris.
- Ke, Wei,Sun, Na-Bo,Wu, Hong-Ke
-
p. 1233 - 1238
(2013/09/23)
-
- Synthesis and bioactivities of novel thioether/sulfone derivatives containing 1,2,3-thiadiazole and 1,3,4-oxadiazole/thiadiazole moiety
-
A series of new thioether/sulfone compounds containing 1,2,3-thiadiazole and 1,3,4-oxadiazole/1,3,4-thiadiazole moiety were synthesized, the structures of all products were confirmed by IR, 1H NMR, 13C NMR, and element analysis. Preliminary antifungal activity test showed that compound 8a exhibited moderate antifungal activity against Fusarium oxysporum at 50 μg/mL. Preliminary antiviral activity results showed that compounds 7a, 7c, 7d, 8a, and 9a displayed high antiviral activity against tobacco mosaic virus. The present work demonstrates that thioether/sulfone heterocyclic derivatives could be considered as new lead compounds for antiviral studies.
- Xu, Wei-Ming,Li, Shi-Ze,He, Ming,Yang, Song,Li, Xiang-Yang,Li, Pei
-
supporting information
p. 5821 - 5824
(2013/10/22)
-
- Microwave assisted synthesis, antifungal activity and DFT theoretical study of some novel,1,2,4-triazole derivatives containing the 1,2,3-thiadiazole moiety
-
In order to investigate the biological activity of 1,2,4-triazole compounds, seventeen novel 1,2,4-triazole derivatives containing 1,2,3-thiadiazole moieties were synthesized by multi-step reactions under microwave assisted conditions. The structures were characterized by 1H-NMR, 13C-NMR, MS and elemental analyses. The target compounds were evaluated for their in vivo fungicidal activities against Corynespora cassiicola, Pseudomonas syringae pv. Lachrymans, and Pseudoperonospora cubensis, and the results indicated that some of the title compounds displayed good fungicidal activities. Theoretical calculations on the title compounds were carried out at the B3LYP/6-31G (d,p). level. The full geometry optimization was carried out using the 6-31G(d,p) basis set, and the frontier orbital energy, atomic net charges were discussed, and the structure-activity relationships were also studied.
- Sun, Na-Bo,Fu, Jian-Qun,Weng, Jian-Quan,Jin, Jian-Zhong,Tan, Cheng-Xia,Liu, Xing-Hai
-
p. 12725 - 12739
(2013/11/06)
-
- Synthesis, bioactivity and DFT structure-activity relationship study of novel 1,2,3-thiadiazole derivatives
-
A series of novel 1,2,3-thiadiazole derivatives were designed and synthesized. Their structures were characterized by 1H NMR, MS and HRMS. The bioactivity tests indicated that compound 9b exhibits a favorable KARI inhibition rate, and some of these novel compounds also showed moderate herbicidal activity against Brassica campestris. Springer Science+Business Media B.V. 2012.
- Liu, Xing-Hai,Zhao, Wei-Guang,Wang, Bao-Lei,Li, Zheng-Ming
-
p. 1999 - 2008
(2013/02/23)
-
- Microwave synthesis and biological activity of hydrazone derivatives containing 1,2,3-thiadiazole
-
A new group of hydrazone derivatives containing 1,2,3-thiadiazole moiety were synthesized under microwave irradiation. The structures of the present hydrazone derivatives were characterized by 1H NMR, MS and elemental analysis. The biological activities of the presents compunds were investigated. The bioassay results indicated that some of these compounds exhibit moderate fungicidal activities, one compound showed 100 % inhibitory activity on cotyledon root of cucumber and all the compounds displayed no insecticidal activity.
- Liu, Xing-Hai,Weng, Jian-Quan,Tan, Cheng-Xia
-
scheme or table
p. 4064 - 4066
(2012/01/12)
-
- Synthesis and antimicrobial activity of pyridopyrazole and pyrazolo[3,4-d]dihydrothiazole
-
6-Methyl-1,3-dihydro-4H,7H-pyrazolo[2,3-c]pyridine-4-one (4) were synthesized by microwave as well as conventional method. The reaction time reduced 10 times than that of conventional method. The pyrazolo[3,4-d] dihydrothiazole (8) were synthesized by reacting phenylisothiocyanate with 1-carbethoxy-5-amino-pyrazol-4-ene-3-one and were screened for their antimicrobial activities.
- Deshmukh,Deshmukh,Jagtap,Suryavanshi,Jadhav,Anbhule
-
experimental part
p. 613 - 616
(2010/07/08)
-
- Controlled release of volatile aldehydes and ketones from dynamic mixtures generated by reversible hydrazone formation
-
Delivery systems generated by reversible hydrazone formation from hydrazine derivatives (see Fig. 1) and carbonyl compounds in H2O efficiently increase the long-lastingness of volatile aldehydes and ketones (R 1R2C=O) in various perfumery applications. The hydrazones are usually obtained in an (E) configuration at the imine double bond (NHN=C) and, in the case of aliphatic acylhydrazones R′CO-NH-N=CR 1R2 (R′ = alkyl), as syn and anti conformers with respect to the amide bond (CO-NHN). An average free-energy barrier of ca. 78kJ/mol was determined for the amide-bond rotation by variable-temperature 1H-NMR measurements (Fig. 2). In the presence of H2O, the hydrazone formation is entirely reversible, reaching an equilibrium composed of the hydrazine derivative, the carbonyl compound, and the corresponding hydrazone. Kinetic measurements carried out by UV/VIS spectroscopy showed that the same equilibrium was reached for the formation and hydrolysis of the hydrazone. Rate constants are strongly pH-dependent and increase with decreasing pH (Table 1). The influence of the hydrazine structure on the rate constants is less pronounced than the pH effect, and the presence of surfactants reduces the rate of equilibration (Tables 1 and 3). The full reversibility of the hydrazone formation allows to prepare dynamic mixtures by simple addition of a hydrazine derivative to several carbonyl compounds. Dynamic headspace analysis on dry cotton showed that the presence of a hydrazine derivative significantly increased the headspace concentrations of the different carbonyl compounds as compared to the reference sample without hydrazine (Table 4). The release of the volatiles was found to be efficient for fragrances with high vapor pressures and low H2O solubility. Furthermore, a special long-lasting effect was obtained for the release of ketones. The simplicity of generating dynamic mixtures combined with the high efficiency for the release of volatiles makes these systems particularly interesting for practical applications and will certainly influence the development of delivery systems in other areas such as the pharmaceutical or agrochemical industry.
- Levrand, Barbara,Fieber, Wolfgang,Lehn, Jean-Marie,Herrmann, Andreas
-
p. 2281 - 2314
(2008/03/29)
-
- USE OF DYNAMIC MIXTURES FOR A CONTROLLED RELEASE OF FRAGRANCES
-
The present invention relates to a delivery system in the form of a dynamic mixture obtained by reacting together, in the presence of water, at least one hydrazine derivative with at least one perfuming, flavoring, insect repellent or attractant, bactericide and/or fungicide aldehyde or ketone. The invention's mixture is capable of releasing in a controlled and prolonged manner said aldehyde or ketone in the surrounding environment. Furthermore, the present invention concerns also the use of said dynamic mixtures as perfuming ingredients as well as the perfuming compositions or perfumed articles comprising the invention's mixtures.
- -
-
Page/Page column 34-38
(2008/06/13)
-
- Preparation of 2-phenylsemicarbazides
-
2-Phenylsemicarbazides are prepared by a multi-step process involving: (a) treating a phenylhydrazine, or salt thereof, with a chloroformate; (b) adding phosgene; (c) treating the resulting product with an amine; and (d) hydrolyzing the resulting acylated semicarbazide. The reaction can proceed through a Δ2 -1,3,4-oxadiazolin-5-one intermediate formed with heating in step (b). Certain of the products are novel compounds.
- -
-
-
- ELECTRON DEFICIENT HETEROAROMATIC AMMONIOAMIDATES, XIX. N-(3-QUINAZOLINIO)AMIDATES, VII. THE PHOTOCHEMISTRY OF N-(3-QUINAZOLINIO)AMIDATES IN THE PRESENCE OF AMINES AND OF ACETAMIDE
-
Irradiation by Pyrex-filtered light of the quinazolinioamidates 1c-1f and of the dimers 2a and 2b in butylamine, of compound 2b in benzylamine and morpholine, and in the presence of acetamide in dioxane or dichloromethane, as well as of the adducts 5a and 5b in dichloromethane leads to complex mixtures of Type 6-16 products.While the compounds 6-9 are the products of Type II cleavage processes of the Type 3-5 adducts, the parent quinazolines 12 are formed from the amidates 1 themselves, amides 14 being the co-products in both cases.Compound 10a is formed by deacetylation of 9a during work-up, while compound 11b is a secondary photosubstitution product of 12b by the solvent dioxane.At least part of the compounds 13, 15 and 16 is the result of dark reactions.
- Barta-Szalai, G.,Fetter, J.,Lempert, K.,Moller, J.
-
p. 253 - 266
(2007/10/02)
-