991. Triazoles. Part VII. Syntheses of substituted 1,2,4-triazoles

Browne, E. J.; Polya, J. B.

doi:10.1039/jr9620005149

Cited by 16 publications

(12 citation statements)

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“…These were prepared by reaction of the corresponding methyl/ethyl esters 2a-f with hydrazine hydrate following literature methods [ 17 , 18 , 19 ].…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Antibacterial and Antifungal Activity of 4-Substituted-5-Aryl-1,2,4-Triazoles

Colanceska-Ragenovic

Dimova

Kakurinov³

et al. 2001

Molecules

120

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A few 4-allyl/amino-5-aryl-1,2,4-triazoles were synthesized and tested for antibacterial and antifungal effects against Escherichia coli, Bacillus subtilis, Salmonella enteritidis, Staphylococcus aureus, Aspergillus niger and Candida albicans. 4-Allyl-5-aryl-1,2,4-triazoles were obtained by the oxidative cyclization of the appropriate 1-substituted-4-allylthiosemicarbazides and 4-amino-5-aryl-1,2,4-triazoles were obtained by cyclization of the potassium salts of appropriately substituted dithiocarbazinic acids with hydrazine hydrate. The new synthesized compounds were characterized using IR, 1H- NMR, 13C-NMR and UV spectral data together with elemental analysis.

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“…These were prepared by reaction of the corresponding methyl/ethyl esters 2a-f with hydrazine hydrate following literature methods [ 17 , 18 , 19 ].…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Antibacterial and Antifungal Activity of 4-Substituted-5-Aryl-1,2,4-Triazoles

Colanceska-Ragenovic

Dimova

Kakurinov³

et al. 2001

Molecules

120

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“…6,7-Dihydro-3-(5-nitro-2-furyl)-5H-imidazo [2,[1][2][3][4][5] thiazolium Bromide (3a).-A mixture of la (20.4 g, 0.2 mole) and 2a4 (46.8 g, 0.2 mole) in absolute ethanol (5600 ml) was refluxed for 4 hr. The reaction mixture was cooled and filtered to yield 58.0 g (91%) of product decomposing at 242-244°.…”

Section: Methodsmentioning

confidence: 99%

“…(1) all of the compounds are active against Proteus vulgaris and Pseudomonas aeruginosa; (2) there is little difference in activity between the free base and its salts (compare 3a and 3b with 4); (4) C-methyl substitution and ring expansion cause a decrease in activity (compare 3c, 3d, 3e, 3f, and 3g with 3b); and (4) insertion of a vinyl group (10) between the two hetero rings has little effect on activity.…”

mentioning

confidence: 99%

5,6-Dihydro-3-(5-nitro-2-furyl)imidazo[2,1-b]thiazoles and Acid Addition Salts¹

Snyder¹,

Benjamin²

1966

J. Med. Chem.

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Yol. 9 B. Irreversibility of the Disproportionation.-Cystamine dihydrochloride (0.5 mmole) was heated with 0.5 mmole of phenyl disulfide, o-chlorophenyl disulfide, or o-hvdroxymethylphenyl disulfide, as usual for disproportionation experiments, in 10 ml of water at 100°for 72 hr. The three aryl disulfides were recovered unchanged (mixture melting point and infrared spectrum) in yields of 99, 104, and l()Lr0 respectively.C. Material Balance in the Disproportionation of 2-Aminoethyldithiobenzene Hydrochloride (10).-An aqueous solution of 10 (0.2338 g, 1.054 mmoles) in water (10 ml) was heated at 08°e xactly as in the disproportionation of 2 -7, except that a 10-day period was used to assure nearly complete reaction. Phenyl disulfide was extracted with CHCh; yield, 105.8 mg (92R ): mj) and inntp 58-59°( infrared spectrum identical with that of phenyl disulfide). Thin layer chromatography was performed on this solid, along with the aqueous phase and appropriate authentic samples, on Eastman Chromagram sheet (Type K 301K: previously activated at 110°for 0.5 hr). Development with 957) acetic acid for 2 hr and exposure to iodine vapor showed one spot, with li; 0.81 (identical witli authentic phenyl disulfide) and only two other spots, with li¡ values of 0.40 and 0.06 corresponding to the authentic samples of cystamine dihydrochloride and 10, respectively.The aqueous phase was evaporated under reduced pressure to a white residue. The residue was rubbed with cold absolute ethanol, which removed 10 but left most of the cystamine salt. Evaporation of the ethanol left crude 10. Several applications of this procedure finally separated 29.6 mg (13$c•) of 10, mp and mmp 127-131°, and 102.6 mg (S6C)) of cystamine dihvdro-chloride, mp and mmp 218-220°dec. Infrared spectra for 10 and the cystamine salt were identical with those of authentic material. Since thin layer chromatography showed that, only three materials were present and since separation showed these materials to be the two symmetrical disulfides (86-92'))) and unchanged 10 (13')), evidently still containing a little cystamine salt), the disproportionation must proceed rather cleanly with rattier slight formation of by-products.Photochemical Disproportionation of Disulfides 2-7 and 9. Aqueous solutions of 1 mmole of unsymmetrical disulfide in 20 ml of water (0.05 .1/) in 50-ml Pyrex flasks23 were irradiated at a distance of 12.5 cm with an ultraviolet source (l()()-w Hanovia ultraviolet lain]), Engelhard Industries Inc.. Newark, N. J.) for 25 min at room temperature. Isolations and calculations were done in the same maimer described for thermal disproportionation.Acknowledgment.-We arc indebted to I)rs. T. It. Sweeney, D. P. Jacobus, and P. Goad for helpful suggestions, as well as for testing and for certain materials mentioned above. The research was supported by the V. S. Army Medical Research and Development Command, Department of the Army, under Research Contract• No. DA-49-193-MD-2030. (24,i liumoyentOUS solution of sparingly .soluble 9 was prepared by dissolvi...

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“…3,5-Disübstitüe-1,2,4-triazol bileşiklerin sentezi için genel metod, alkilhidrazinler ile imin esterlerin kondenzasyonudur (Postovskii & Vereshchagina, 1954;Brown & Polya, 1962) Aril sübstütientlerini taşıyan 1,2,4-triazol türevleri, alkil gruplarını taşıyanlara nazaran daha kararlıdırlar ve reaksiyona girme yatkınlıkları daha fazladır. 1,2,4-Triazol içeren Schiff bazları ilaç ve koordinasyon kimyası için önemli bileşiklerdir ve antibiyotik, antitümör, antipsikolojik, antiallerjik gibi bazı önemli ilaçların sentezinde başlatıcı madde olarak kullanılmışlardır (Barton & Ollis, 1979;Ingold, 1969;Layer, 1963).…”

Section: Introductionunclassified

3-Fenil-5-(4-pridil)-1,2,4-triazol Molekülünün DFT(B3LYP/B3PW91)/HF ile Spektroskopik, Geometrik,Termodinamik ve Elektronik Analizi

Kotan¹,

Yüksek²

2019

European Journal of Science and Technology

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Öz 3-Fenil-5-(4-pridil)-1,2,4-triazol bileşiğinin moleküler geometrik optimizasyonu 6-311G(d,p) ve 3-21G temel setinde DFT(B3LYP, B3PW91)/ HF metodları kullanılarak elde edilmiştir. Böylece, bileşiğin en kararlı geometrik şekli çeşitli metod ve setlerle bulunmuştur. Deneysel spektral incelenmeler FT-IR değerleri ve 1 H/ 13 C-NMR kimyasal kaymaları kullanılarak gerçekleştirilmiştir. Geometrik yapı analizleri (bağ açıları, bağ uzunlukları), Proton/ Karbon NMR kimyasal kaymaları, termodinamik parametreler, HOMO-LUMO analizleri, elektronik özellikler, mulliken yükleri, titreşimsel dalgalanmalar, dipol momenti, başlıca molekülünün toplam enerjisi "Gaussian 09W" paket programı kullanılarak hesaplanmıştır. Sonuçlar, GaussView5.0 programında değerlendirilmiştir. Hesaplamalı IR verileri Veda4f programında belirlenmiş ve bu hormonik titreşim frekansları belirli faktörler ile ölçeklendirilmiştir. Deneysel değerler literatürden alınmıştır. Deneysel spektral değerler hesaplanan IR verileri ile karşılaştırılmıştır. Proton Nükleer Manyetik Rezonans (1 H-NMR) ve Karbon-13 Nükleer Manyetik Rezonans (13 C-NMR) spektral değerleri, gaz fazında ve DMSO çözücüsünde GIAO yöntemine göre hesaplanmıştır. Bu değerler deneysel proton / karbon nmr verileriyle karşılaştırılmış ve sonuçlara göre regresyon analizi yapılmıştır. Ayrıca farklı yöntemlerle elde edilen ve fonksiyonel olan teorik sonuçlar birbiriyle karşılaştırılmıştır. Bundan başka, HOMO-LUMO enerji hesaplamaları ile kimyasal sertlik (η), elektronegatiflik (χ), iyonlaşma potansiyeli (I), kimyasal yumuşaklık (σ), elektron ilgisi (A) gibi parametreler belirlenmiştir. Elektron yoğunluğu moleküler yüzeyler, elektron spin potansiyeli (ESP), moleküler elektrostatik potansiyel (MEP), toplam yoğunluk ve kontur haritaları belirlenmiştir. Böylece farklı metodlar, fonksiyonlar ve setler ile molekülün tüm teorik parametreleri hesaplanmıştır. Sonuçta bu veriler karşılaştırılmış ve en uygun yöntem ve set bulunmuştur.

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991. Triazoles. Part VII. Syntheses of substituted 1,2,4-triazoles

Cited by 16 publications

References 0 publications

Synthesis, Antibacterial and Antifungal Activity of 4-Substituted-5-Aryl-1,2,4-Triazoles

Synthesis, Antibacterial and Antifungal Activity of 4-Substituted-5-Aryl-1,2,4-Triazoles

5,6-Dihydro-3-(5-nitro-2-furyl)imidazo[2,1-b]thiazoles and Acid Addition Salts¹

3-Fenil-5-(4-pridil)-1,2,4-triazol Molekülünün DFT(B3LYP/B3PW91)/HF ile Spektroskopik, Geometrik,Termodinamik ve Elektronik Analizi

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991. Triazoles. Part VII. Syntheses of substituted 1,2,4-triazoles

Cited by 16 publications

References 0 publications

Synthesis, Antibacterial and Antifungal Activity of 4-Substituted-5-Aryl-1,2,4-Triazoles

Synthesis, Antibacterial and Antifungal Activity of 4-Substituted-5-Aryl-1,2,4-Triazoles

5,6-Dihydro-3-(5-nitro-2-furyl)imidazo[2,1-b]thiazoles and Acid Addition Salts1

3-Fenil-5-(4-pridil)-1,2,4-triazol Molekülünün DFT(B3LYP/B3PW91)/HF ile Spektroskopik, Geometrik,Termodinamik ve Elektronik Analizi

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5,6-Dihydro-3-(5-nitro-2-furyl)imidazo[2,1-b]thiazoles and Acid Addition Salts¹