ChemInform Abstract: Synthesis of 5‐Iodo‐1,2,3‐triazoles from Organic Azides and Terminal Alkynes: Ligand Acceleration Effect, Substrate Scope, and Mechanistic Insights.

Barsoum, David N.; Brassard, Christopher J.; Deeb, Jason H. A.; Okashah, Najeah; Sreenath, Kesavapillai; Simmons, J. Tyler; Zhu, Lei

doi:10.1002/chin.201406158

Cited by 2 publications

(4 citation statements)

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“…The current work was triggered by our previous observations on the rapid formation of 1-iodoalkynes from terminal alkynes using in situ generated electrophilic I 2 from CuI 2 (Scheme ). − Similarly, we postulated that in situ formed cyanogen, (CN) 2 , and Cu(I) from Cu(CN) 2 would transform terminal alkynes to 1-cyanoalkynes.…”

Section: Introductionmentioning

confidence: 78%

“…Aromatic azides were synthesized by diazotization of aniline derivatives. Other organic azides were synthesized by nucleophilic substitution of organic halides and NaN 3 …”

Section: Methodsmentioning

confidence: 99%

“…Other organic azides were synthesized by nucleophilic substitution of organic halides and NaN 3 . 18 CAUTION! Low molecular weight organic azides and Cu(ClO 4 ) 2 •6H 2 O are potentially explosive.…”

Section: ■ Conclusionmentioning

confidence: 99%

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Synthesis of 1-Cyanoalkynes and Their Ruthenium(II)-Catalyzed Cycloaddition with Organic Azides to Afford 4-Cyano-1,2,3-triazoles

2018

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A new method to convert terminal alkynes under relatively mild conditions to 1-cyanoalkynes using in situ formed cyanogen is described. 1-Cyanoalkynes have a higher reactivity than terminal alkynes in the ruthenium(II)-catalyzed regiospecific azide-alkyne cycloaddition to afford 4-cyano-1,2,3-triazoles. A mechanistic proposal different from the one that terminal alkynes adopt under the same reaction conditions is proposed. This work provides a new and convenient two-step sequence to prepare 4-cyano-1,2,3-triazoles from terminal alkynes and organic azides.

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Section: Introductionmentioning

confidence: 78%

“…Aromatic azides were synthesized by diazotization of aniline derivatives. Other organic azides were synthesized by nucleophilic substitution of organic halides and NaN 3 …”

Section: Methodsmentioning

confidence: 99%

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Synthesis of 1-Cyanoalkynes and Their Ruthenium(II)-Catalyzed Cycloaddition with Organic Azides to Afford 4-Cyano-1,2,3-triazoles

2018

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“…The tris(organosilyl)methyllithium compounds were prepared using the published methodologies . Bromomethyl derivatives were synthesized using phosphorus tribromide (PBr 3 ) in dichloromethane at room temperature . Finally, the reaction of tris(trimethylsilyl)methyllithium and carbon disulphide with bromomethyl derivatives was followed in THF at 0 and −46°C for synthesis of sila‐thioalkynetriazole ( 3a–i ) and sila‐mercapto‐thionetriazole ( 4a–i ) analogues, respectively, in excellent yields .…”

Section: Resultsmentioning

confidence: 99%

Study of the Cytotoxic and Bactericidal Effects of Sila‐substituted Thioalkyne and Mercapto‐thione Compounds based on 1,2,3‐Triazole Scaffold

Mousazadeh

Milani

Zarghami

et al. 2017

Basic Clin Pharma Tox

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A series of sila-organosulphur compounds containing 1,2,3-triazole cores were screened for their cytotoxic activity on human breast cancer cell line MCF-7. Most of the tested compounds exhibited moderate-to-good activity against the cancer cells. Especially, the compound 4-((2-(trimethylsilyl)ethynylthio)methyl)-1-benzyl-1H-1,2,3-triazole (3a) from series of sila-substituted thioalkyne 1,2,3-triazoles (STATs) and the compounds 3-(1-benzyl-1H-1,2,3-triazol-4-yl)-1-mercapto-1,1-bis(trimethylsilyl)propane-2-thione (4a) and 1-mercapto-1,1-bis(trimethylsilyl)-3-(1-phenethyl-1H-1,2,3-triazol-4-yl)propane-2-thione (4e) from series of sila-substituted mercapto-thione 1,2,3-triazoles (SMTTs) exhibited promising cytotoxicity against MCF-7 with IC values of 35.17, 32.63 and 30.3 μg/mL, respectively. In addition, the possible mechanisms for inhibition of cell growth and induction of apoptotic cell death were explored by DAPI staining, cell cycle analysis and qRT-PCR. The synthetic compounds were evaluated for their in vitro antibacterial activities, and as a result, the most prominent effects were observed for 3e and 4e. Especially, 3e was found to be quite active against all the tested strains with the MIC values ranging from 15 to 62 μg/mL, except P. aeruginosa. The results of the time-kill assay suggested that the compound of 3e completely inhibited the growth of both gram-negative bacteria, A. baumannii, and gram-positive bacteria, S. aureus. In addition, SEM analysis confirmed morphostructural damage of the bacteria. Our findings could be applicable for developing dual-targeting anticancer/antibacterial therapeutics.

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ChemInform Abstract: Synthesis of 5‐Iodo‐1,2,3‐triazoles from Organic Azides and Terminal Alkynes: Ligand Acceleration Effect, Substrate Scope, and Mechanistic Insights.

Cited by 2 publications

References 1 publication

Synthesis of 1-Cyanoalkynes and Their Ruthenium(II)-Catalyzed Cycloaddition with Organic Azides to Afford 4-Cyano-1,2,3-triazoles

Synthesis of 1-Cyanoalkynes and Their Ruthenium(II)-Catalyzed Cycloaddition with Organic Azides to Afford 4-Cyano-1,2,3-triazoles

Study of the Cytotoxic and Bactericidal Effects of Sila‐substituted Thioalkyne and Mercapto‐thione Compounds based on 1,2,3‐Triazole Scaffold

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