Synthesis of Novel N-(R)-2-(1-Adamantyl)-1H-Benzimidazole-5(6)-Carboxamide, Carbohydrazide and 1,3,4-Oxadiazole Derivatives

2020 ◽  
Vol 17 ◽  
Author(s):  
Marina Soselia ◽  
Medea Lomidze ◽  
Tamar Tabatadze ◽  
Davit Zurabishvili ◽  
Marina Trapaidze ◽  
...  
Keyword(s):  
Hydrazine Hydrate ◽  
Acid Chloride ◽  
Cyclization Reaction ◽  
Aromatic Acids ◽  
Acyl Chlorides ◽  
First Case ◽  
Adamantanecarboxylic Acid ◽  
Oxadiazole Derivatives ◽  
Direct Condensation

: A novel series of benzimidazole-5(6)-carboxamide 3a-g, carbohydrazide 5a-e and 1,3,4-oxadiazole 6a-g derivatives bearing adamantane moiety were synthesized. The synthesis of benzimidazole heterocycle was performed by direct condensation/cyclization reaction of 1-adamantanecarboxylic acid with methyl 3,4-diaminobenzoate in Trimethylsilyl Polyphosphate (PPSE). The obtained Methyl 2-(1-adamantyl)-1H-benzimidazole-5(6)-carboxylate was converted to desired carboxamide and carbohydrazide derivatives in two different ways. In the first case, the synthesized ester after hydrolysis was converted to acid chloride and subsequently coupled with different aromatic and heterocycle amines to give carboxamide derivatives. In the second case, treatment with hydrazine hydrate gave corresponding 2-(1-adamantyl)-1Hbenzimidazole-5(6)-carbohydrazide which was coupled with some acyl chlorides to give appropriate carbohydrazide derivatives and with some aromatic acids to give 1,3,4-oxadiazole derivatives.

scholarly journals A Synthesis of 4-Chloro-2-(trichloromethyl)pyrimidines and Their Study in Nucleophilic Substitution

Synthesis ◽  
2018 ◽  
Vol 51 (02) ◽  
pp. 530-537 ◽  
Author(s):  
Moisés Romero-Ortega ◽  
Michelle Trujillo-Lagunas ◽  
Ignacio Medina-Mercado ◽  
Ivann Zaragoza-Galicia ◽  
Horacio Olivo
Keyword(s):  
Nucleophilic Substitution ◽  
Intramolecular Cyclization ◽  
Nitrogen Heterocycles ◽  
Cyclization Reaction ◽  
Substitution Reactions ◽  
Pyrimidine Derivatives ◽  
One Pot ◽  
Acyl Chlorides ◽  
Nucleophilic Substitution Reactions ◽  
One Pot Synthesis

A convenient two-step, one-pot synthesis of 4-chloro-2-(trichloromethyl)pyrimidines starting from 2-(trichloromethyl)-1,3-diazabutadienes is described. These nitrogen heterocycles were prepared by a sequential acylation/intramolecular cyclization reaction between 2-(trichloromethyl)-1,3-diazabutadienes and acyl chlorides in the presence of triethylamine followed by treatment with POCl3. This is the first report for the synthesis of this type of 4-chloro-2-(trichloromethyl)pyrimidine derivatives and serves as a source for a wide variety of other substituted pyrimidines by nucleophilic substitution reactions.

ChemInform Abstract: A Novel Cyclization Reaction Between 2,3-Bis(trimethylsilyl)buta-1,3-diene and Acyl Chlorides with Straightforward Formation of Polysubstituted Furans.

ChemInform ◽  
2008 ◽  
Vol 39 (5) ◽  
Author(s):  
Francesco Babudri ◽  
Stefania R. Cicco ◽  
Gianluca M. Farinola ◽  
Linda C. Lopez ◽  
Francesco Naso ◽  
...  
Keyword(s):  
Cyclization Reaction ◽  
Acyl Chlorides

scholarly journals Design, Synthesis and Characterization of Novel Arylamides Containing 1,2,4-triazole Nuclei for Possible Antimicrobial Activity

2004 ◽  
Vol 1 (5) ◽  
pp. 228-230 ◽  
Author(s):  
S. R. Dhol ◽  
P. M. Gami ◽  
R. C. Khunt ◽  
A. R. Parikh
Keyword(s):  
Antimicrobial Activity ◽  
Hydrazine Hydrate ◽  
Carbon Disulfide ◽  
Acid Chloride ◽  
Potassium Hydroxide ◽  
Synthesis And Characterization ◽  
Design Synthesis ◽  
Elemental Analyses

Diphenyl aceto hydrazide on reaction with carbon disulfide and potassium hydroxide gave potassiumα,α-diphenyl acetamido dithiocarbamate, which on cyclisation with hydrazine hydrate yielded key intermediate 3-mercapto-4,N-amino-5-benzhydryl-1,2,4-triazoles. The key intermediate on condensation with different acid chloride afforded our titled compounds. The synthesised compounds have been confirmed elemental analyses and further supported by spectral data. All the synthesised compounds have been evaluated for theirin vitroin vitro antimicrobial activity.

Synthesis of N,N'-Diacylhydrazines and their use in Various Synthetic Transformations

2021 ◽  
Vol 25 ◽  
Author(s):  
Mohammed A. Baashen
Keyword(s):  
Hydrazine Hydrate ◽  
Carboxylic Acids ◽  
Crown Ethers ◽  
Current Work ◽  
Acyl Chlorides ◽  
Synthetic Routes ◽  
Synthetic Transformations

: The current work reviews the synthesis of N,N'-diacylhydrazines and their use in various synthetic transformationshave been reviewed. Three synthetic routes are commonly used to produce N,N'-diacylhydrazines. They are produced through the coupling of acyl chlorides and carbohydrazides, the reaction of hydrazine hydrate and carboxylic acids or isocyanates, and the dimerization of carbohydrazides. N,N'-Diacylhydrazines are involved in many synthetic transformations to produce various types of compounds. They can be oxidized to produce the corresponding esters and act as precursors in the synthesis of various heterocycles such as 1,3,4-oxadiazoles, 1,3,4-thiadiazoles, 1,2,4-triazoles, pyrazoles, tetrazines, and crown ethers.

A novel cyclization reaction between 2,3-bis(trimethylsilyl)buta-1,3-diene and acyl chlorides with straightforward formation of polysubstituted furans

2007 ◽  
pp. 3756 ◽  
Author(s):  
Francesco Babudri ◽  
Stefania R. Cicco ◽  
Gianluca M. Farinola ◽  
Linda C. Lopez ◽  
Francesco Naso ◽  
...  
Keyword(s):  
Cyclization Reaction ◽  
Acyl Chlorides

scholarly journals Synthesis and Anticancer Activity of Novel Oxadiazole Functionalized Pyrazolo[3,4-b]pyridine Derivatives

2021 ◽  
Vol 33 (6) ◽  
pp. 1331-1335
Author(s):  
Bhadru Bhukya ◽  
Hanmanthu Guguloth
Keyword(s):  
Breast Cancer ◽  
Cervical Cancer ◽  
Colon Cancer ◽  
Liver Cancer ◽  
Anticancer Activity ◽  
Hydrazine Hydrate ◽  
Pyridine Derivatives ◽  
Aromatic Acids ◽  
Phosphoryl Chloride ◽  
Micromolar Concentration

A series of novel oxadiazole functionalized pyrazolo[3,4-b]pyridine derivatives (6a-n)was synthesized using 6-thiophenyl-4-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-3-amine (1) through reaction with 2-bromoethyl acetate, followed by hydrazine hydrate to afford hydrazide derivatives (5). These compounds were further treated with aromatic acids in the presence of phosphoryl chloride and obtained oxadiazole functionalized pyrazolo[3,4-b]pyridine derivatives (6a-n). All the synthesized compounds 6a-n were screened for anticancer activity against four cancer cell lines such as HeLa - cervical cancer (CCL-2); COLO 205-colon cancer (CCL-222); HepG2-liver cancer (HB-8065); MCF7-breast cancer (HTB-22). Compounds 6i, 6m and 6n were found to have more prominent anticancer activity at micromolar concentration.

Synthesis of pyridine clubbed 2,5-disubstituted-1,3,4-oxadiazole derivatives shows potent antimicrobial activity.

2020 ◽  
Vol 17 ◽  
Author(s):  
Pratima Katiyar ◽  
Manjul Pratap Singh
Keyword(s):  
Antimicrobial Activity ◽  
Structure Elucidation ◽  
Aromatic Acids ◽  
Pyridine Moiety ◽  
Antimicrobial Studies ◽  
Oxadiazole Derivatives ◽  
Microbial Strains ◽  
Spectral Data Analysis ◽  
Eskape Pathogens

: In the present study, series of 2,5-disubstituted-1,3,4 oxadiazole analogues retaining pyridine moiety were synthesized (4a-j) by reacting various substituted aromatic acids and isonicotinohydrazide by using POCl3 as cycling agent. The structure elucidation of all the synthesized compounds was done by chromatographic data and the spectral data analysis. The synthesized compounds were evaluated for their in-vitro antimicrobial activity against various strains of ESKAPE pathogens. Antibacterial activity was performed against Bacillus subtilis, Escherichia coli, Staphylococcus aureus and Pseudomonas aeruginosa, while antifungal activity was assayed against Candida albicans and Aspergillus spp. The result of invitro antimicrobial studies of all the synthesized compounds revealed that compound 4d and 4f exhibited prompt activity against selected microbial strains equally compared to Cefixime and Econazole used as reference drugs.

scholarly journals Expeditious synthesis of 1,3,4-oxadiazole derivatives via sydnones

2008 ◽  
Vol 73 (2) ◽  
pp. 131-138 ◽  
Author(s):  
Ravindra Kamble ◽  
B.S. Sudha ◽  
D.G. Bhadregowda
Keyword(s):  
Acetic Anhydride ◽  
Microwave Irradiation ◽  
Hydrazine Hydrate ◽  
Reaction Times ◽  
Elemental Analyses ◽  
Oxadiazole Derivatives

The clean cyclization of chalcones (1a-c/2a-c) with hydrazine hydrate under microwave irradiation afforded pyrazolines derivatised with sydnone (3d-i/4d-i), which underwent 1,3-dipolar cyclo-addition with acetic anhydride to form pyrazolines appended with 1,3,4-oxadiazoles (5g-l/6g-l). The newly synthesized compounds were confirmed by spectral and elemental analyses. In comparison to classical heating, the results indicate that microwave irradiation affords higher yields, shorter reaction times (4-12 min) and cleaner reactions.

scholarly journals SYNTHESIS, SPECTRAL CHARACTERIZATION AND ANTIMICROBIAL SCREENING OF SUBSTITUTED 1,3,4-OXADIAZOLE DERIVATIVES

2010 ◽  
Vol 18 (18) ◽  
pp. 11-18
Author(s):  
Anees A Siddiqui ◽  
Asif Husain ◽  
M Shaharyar ◽  
Mohd Rashid ◽  
Ravinesh Mishra ◽  
...  
Keyword(s):  
Aromatic Acids ◽  
E Coli ◽  
Phosphorous Oxychloride ◽  
Diffusion Technique ◽  
Oxadiazole Derivatives ◽  
Bacteria And Fungi ◽  
Hydroxy Quinoline ◽  
Different Strains ◽  
Antibacterial And Antifungal

1,3,4-oxadiazoles are important because of its versatile biological actions. In the present study, several 2-(quinoline-8-yloxymethyl)-5-aryl-1,3,4-oxadiazole derivates (IIIa-j) have been synthesized by the condensation of 8-hydroxy quinoline acetyl hydrazide (II) with various aromatic acids in presence of phosphorous oxychloride. The structures of the newly synthesized compounds have been established on the basis of elemental analysis, UV, IR, and 1H NMR spectral data. The synthesized compounds were screened for their in vitro growth-inhibiting activity against different strains of bacteria and fungi viz., S aureus, E. Coli, P. aeruginosa, C. Albicans, A. flavus, and A. fumigates, and the results were compared with the standard such as Ampicillin (50µg/ml) using agar diffusion technique. Compounds IIIc and IIIf were found to be equipotent as ampicillin when tested against the strains of E.Coli where as tested compounds IIIc, IIIf and IIIi showed good antibacterial and antifungal activity when tested against the strains of S. aureus, P. aeruginosa, and C. Albicans.

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