The Smiles rearrangement of 2-tetrazolylthio-3-aminopyridines

Altland, Henry W.

doi:10.1021/jo00883a013

Cited by 26 publications

(8 citation statements)

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“…The formation of 1,3-thiazolo [4,5-b]pyridine, via transformation of 1,2,4-triazine rings [12] or 2-(tetrazolylsulfanyl)pyridin-3-amines containing an aryl substituent in the tetrazole moiety under acidic conditions, has been also reported [13]. Couture and Grandclaudon described the conversion of the C¼O group of N-(2-chloropyridin-3-yl)benzamides to the C¼S group with Lawessons reagent, followed by ring closure providing desired 1,3-thiazolo [5,4-b]pyridines [14].…”

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confidence: 97%

One‐Pot Synthesis of New (1,3‐Thiazolo[5,4‐b]pyridin‐2‐yl)benzenediols and Their Antiproliferative Activities against Human Cancer Cell Lines

Matysiak

Karpińska

Niewiadomy

et al. 2012

Chemistry & Biodiversity

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A one-pot synthesis of new 4-(1,3-thiazolo[5,4-b]pyridin-2-yl)benzene-1,3-diols has been described. The compounds were prepared by the reaction of sulfinylbis[(2,4-dihydroxyphenyl)methanethione] derivatives, with various substituents in the aryl rings, with 2-chloropyridin-3-amines. Their structures were deduced from IR and, (1) H- and (13) C-NMR spectroscopic, mass spectrometric, and elemental analyses. The antiproliferative properties of some of the products against human cancer cell lines were comparable to those of cisplatin. Structure-activity analysis showed that the presence of hydrophobic substituents in both heterocyclic fused and phenyl rings of the compounds improves their biological effects. Further, an additional OH group in the resorcinol moiety reduced the antiproliferative activity.

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confidence: 97%

One‐Pot Synthesis of New (1,3‐Thiazolo[5,4‐b]pyridin‐2‐yl)benzenediols and Their Antiproliferative Activities against Human Cancer Cell Lines

Matysiak

Karpińska

Niewiadomy

et al. 2012

Chemistry & Biodiversity

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“…MS of the compounds were recorded on QSTAR XL hybrid MS/MS system, applied bio systems under electron spray ionization method conditions preparing sample solutions in methanol. 25 : To the substituted isothiocyanates (4a-e) (3.7 g, 20 mmol) and NaN 3 2.0 g (30 mmol) dissolved in 40 ml of water were stirred at reflux for 4 h. After this time, the reaction mixture was cooled, filtered and pH value of the filtrate was adjusted to 3.0 by adding concentrated hydrochloric acid, then white solid obtained and collected by filtration, washed with cold water, and dried under vacuum to give the crude product. The crude product was used directly or purified by crystallization using methanol to yield pure desired 1-substituted-1H-tetrazole-5-thiol (5a-e) (15 mmol) is added to a solution of piperazine in dry acetonitrile (1a-d) (10 mmol), then 1, 3-dibromopropane was added drop wise (10 mmol) (10 mL) and stirred at room temperature for overnight.…”

Section: Materials and Apparatusmentioning

confidence: 99%

“…Initially, substituted isothiocyanates 29 (4a-e) were prepared from substituted anilines following the procedure shown in Scheme 2. As depicted in Scheme 2, reaction between substituted isothiocyanates (4a-e) and sodium azide in water provided 1-substituted -1H-tetrazole-5-thiol 25 (5a-e) in good yield. The mercapto tetrazole (5a-e) formed can exist in thione-thiol tautomeric forms shown in scheme 2 (I and II).…”

Section: Chemistrymentioning

confidence: 99%

Regioselective synthesis and preliminary cytotoxic activity properties of tetrazole appendage N-substituted piperazine derivatives

Dileep¹,

Katiki²,

Rao³

et al. 2017

Org. Commun.

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A series of 1-(4-substituted)-4-(3-((1-(substituted)-1H-tetrazol-5-yl)thio)propyl)piperazine derivatives were (6a-t) synthesized by KF-Al 2 O 3 mediated S-alkylation of 5-thio-substituted tetrazole with 1-(3-chloropropyl)-4-(4-substituted)piperazine. The structures of the newly synthesized compounds were characterized by NMR and MS spectral data. Further, the regioselective formation of C-S bond was unambiguously confirmed by single crystal Xray diffraction. All the synthesized compounds were screened for their in vitro cytotoxic activities against two cancer cell lines: DU-145 (prostate cancer) and HeLa (cervical cancer). These cell lines were utilized in MTT assays and the obtained results were compared to doxorubicin, and their IC 50 values were determined. Among the compounds tested, 6f, 6j, 6m, 6n, 6o, 6q, 6r and 6t showed considerable potent activity, while the compound 6p exhibited significant potent activity against DU-145 and HeLa cancer cell lines compare to standard Doxorubicin.

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“…Earlier works by Lieber 3,4 and Altland 5 groups proposed the presence of such tautomers. However, the accurate structure of 1-substituted tetrazole-5-thiones (A, B) or 1-substituted tetrazole-5-thiol (C) is still unclear, because the current spectral data cannot clearly confirm it.…”

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confidence: 94%

A Facile One-Pot Synthesis of 1-Substituted Tetrazole-5-thiones and 1-Substituted 5-Alkyl(aryl)sulfanyltetrazoles from Organic Isothiocyanates

Han¹,

Lee²,

Kim³

et al. 2012

Bulletin of the Korean Chemical Society

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Treatments of organic isothiocyanates (R-NCS) with NaN 3 in the presence of pyridine in water at room temperature gave corresponding various organic tetrazole-thiones, [S=CN 4 (R)] (R = alkyl or aryl). Isolated products are obtained as white or yellow solids in good yields (76-97%). The molecular structure by X-ray diffraction study for one of products shows the proposed formation. In addition, one-pot synthesis of 1-substituted 5-alkyl(or aryl)sulfanyltetrazoles has been demonstrated. Addition of alkyl or aryl halides into the mixture of organic isothiocyanates, NaN 3 , and pyridine in water at room temperature exclusively formed 1-substituted 5-alkyl(or aryl)sulfanyltetrazoles (S-derivatives) in high yields.

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The Smiles rearrangement of 2-tetrazolylthio-3-aminopyridines

Cited by 26 publications

References 0 publications

One‐Pot Synthesis of New (1,3‐Thiazolo[5,4‐b]pyridin‐2‐yl)benzenediols and Their Antiproliferative Activities against Human Cancer Cell Lines

One‐Pot Synthesis of New (1,3‐Thiazolo[5,4‐b]pyridin‐2‐yl)benzenediols and Their Antiproliferative Activities against Human Cancer Cell Lines

Regioselective synthesis and preliminary cytotoxic activity properties of tetrazole appendage N-substituted piperazine derivatives

A Facile One-Pot Synthesis of 1-Substituted Tetrazole-5-thiones and 1-Substituted 5-Alkyl(aryl)sulfanyltetrazoles from Organic Isothiocyanates

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