Synthesis of new 4-aza-indoles via acyl azides

Doğan, Şengül Dilem; Demirpolat, Eren; Aycan, Mükerrem; Balcı, Metin

doi:10.1016/j.tet.2014.11.057

Cited by 16 publications

(9 citation statements)

References 41 publications

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“…In order to synthesize the target urea derivatives 10a – 10h , azidination reaction was performed on the 2,2′‐[disulfanediylbis(methylene)]dibenzoic acid ( 5 ). In the azidination reaction, acid 5 was initially reacted with ethyl chloroformate in presence of triethylamine, then a solution of NaN 3 in water was added to give azide 9 in 81 % yield ( Scheme ). The azide function was convenient to generate the corresponding isocyanate via Curtius rearrangement .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Disulfide‐Bridged N‐Phenyl‐N′‐(alkyl/aryl/heteroaryl)urea Derivatives and Evaluation of Their Antimicrobial Activities

Doğan

Buran

Gündüz

et al. 2019

Chemistry & Biodiversity

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The discovery of new antimicrobial agents is extremely needed to overcome multidrug-resistant bacterial and tuberculosis infections. In the present study, eight novel substituted urea derivatives (10a-10h) containing disulfide bond were designed, synthesized and screened for their in vitro antimicrobial activities on standard strains of Gram-positive and Gram-negative bacteria as well as on Mycobacterium tuberculosis. According to the obtained results, antibacterial effects of the compounds were found to be considerably better than their antimycobacterial activities along with their weak cytotoxic effects. Molecular docking studies were performed to gain insights into the antibacterial activity mechanism of the synthesized compounds. The interactions and the orientation of compound 10a (1,1'-((disulfanediylbis(methylene))bis(2,1-phenylene))bis(3-phenylurea)) were found to be highly similar to the original ligand within the binding pocket E. faecalis β-ketoacyl acyl carrier protein synthase III (FabH). Finally, a theoretical study was established to predict the physicochemical properties of the compounds. Scheme 1. Synthetic scheme for the preparation of the key compound, 2,2'-[disulfanediylbis(methylene)]dibenzoic acid (5).

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Section: Resultsmentioning

confidence: 99%

Synthesis of Disulfide‐Bridged N‐Phenyl‐N′‐(alkyl/aryl/heteroaryl)urea Derivatives and Evaluation of Their Antimicrobial Activities

Doğan

Buran

Gündüz

et al. 2019

Chemistry & Biodiversity

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“…Acids 12, 13 and hydrazides 14, 15 were further used for acyl azide 1, 16 synthesis. Acyl azides commonly are prepared from carboxylic acids via mixed anhydrides [21][22][23][24] or directly using diphenyl phosphoryl azide 25 or from acyl chlorides. 21 They can also been prepared by nitrosation of hydrazides.…”

Section: Resultsmentioning

confidence: 99%

“…Acyl azides undergo thermal rearrangement in an inert solvents to give isocyanates (Curtius rearrangement), which on reaction with amines lead to the formation of ureas. 22,23,25,27 Thus, heating at reflux acyl azides 1, 16 It should be noted, that the yield and the reaction time are dependent on the number of halogen atoms and their position in an aryl amine ring, e.g., azide 1 reaction with 2,6-dichloroaniline occurred within 4 h, while it needs only 2 h in the other cases. In addition, urea 19 is obtained in a lower yield (53%), and 2,4,6-trichloroaniline did not react with azide 1 under given conditions.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of some aryl (pyrimidin-3-yl)methyl ureas, hydrazones and semicarbazones

Jakubkienė¹,

Zurba²,

Burbuliene³

2016

Arkivoc

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Two methods of synthesis of aryl (pyrimidin-3-yl)methyl ureas were investigated. One of them involved reaction sequence starting with (pyrimidin-3-yl)acetohydrazides to give the corresponding azides, which reacted with aryl amines to form aryl (pyrimidin-3-yl)methyl ureas. The second one was based on a one-pot reaction of (pyrimidin-3-yl)acetic acids with diphenyl phosphoryl azide followed by reaction with aryl amines. Also, some new aryl and (pyrimidin-3-yl) moiety bearing hydrazones and semicarbazones were synthesized.

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“…In this context, based on our research work on the synthesis of nitrogenous heterocyclic compounds, we report here a convenient synthesis of novel derivatives of alkyl 2-[2,4-dioxo-1,2-dihydroquinazolin-3(4H)-yl]benzoates. The preparation of trisubstituted indoles by cyclization of the diarylurea derivatives when refluxed in acetonitrile in the presence of potassium carbonate has been reported by Balci et al 22 In this work, the application of these conditions to dialkyl 2,2′-[carbonylbis(azanediyl)]dibenzoates 6a-g previously prepared, leads to the alkyl 2-(2,4-dioxo-1,2-dihydroquinazolin-3(4H)-yl)benzoates 9a-g (Scheme 4). In this case, the symmetrical urea benzoates give rise to novel quinazolin-2,4-diones 9a-g by intramolecular cyclization, forming a six-membered ring, while ureas that bind to 2-phenylacetic esters, described by Balci et al 22 lead to indole derivatives due to having the longest substituent.…”

Section: Paper Synthesismentioning

confidence: 98%

Synthesis of New Dialkyl 2,2′-[Carbonylbis(azanediyl)]dibenzoates via Curtius Rearrangement

et al. 2021

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The 2-(alkylcarbonyl)benzoic acids obtained by esterification of phthalic anhydride are converted into azide derivatives: alkyl 2-[(azidocarbonyl)amino]benzoates and to ureas: dialkyl 2,2′-[carbonylbis(azanediyl)]dibenzoates. These transformations were carried out using classical Curtius rearrangement conditions in the presence of diphenylphosphoryl azide (DPPA) in a basic medium, followed by hydrolysis. Subsequently, a final condensation reaction of these urea derivatives enabled us to obtain, for the first time, the new alkyl derivatives, alkyl 2-[2,4-dioxo-1,2-dihydroquinazolin-3(4H)-yl]benzoates. All the new compounds obtained in satisfactory yields were characterized by 1H and 13C NMR, and by X-ray crystallographic analysis.

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Synthesis of new 4-aza-indoles via acyl azides

Cited by 16 publications

References 41 publications

Synthesis of Disulfide‐Bridged N‐Phenyl‐N′‐(alkyl/aryl/heteroaryl)urea Derivatives and Evaluation of Their Antimicrobial Activities

Synthesis of Disulfide‐Bridged N‐Phenyl‐N′‐(alkyl/aryl/heteroaryl)urea Derivatives and Evaluation of Their Antimicrobial Activities

Synthesis of some aryl (pyrimidin-3-yl)methyl ureas, hydrazones and semicarbazones

Synthesis of New Dialkyl 2,2′-[Carbonylbis(azanediyl)]dibenzoates via Curtius Rearrangement

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