Organic Sulfur Compounds. Vi. 5-(2-Thienylmethyl)-1,2,4-Triazole Derivatives

Roman, Gheorghe; Manciulea, Ileana; Ardeleanu, Rodinel; Dumitrescu, Lucia

doi:10.1515/hc.2005.11.3-4.311

Cited by 3 publications

(5 citation statements)

References 11 publications

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“…The compound 3a was obtained the same method. 17 The structure of new obtained compounds was confirmed by elemental analysis as well as IR and 1 H NMR spectra.…”

Section: Resultsmentioning

confidence: 80%

“…In this case study compounds possessing, phenyl, ethyl, 4-tolyl, 4-bromophenyl, 4-methoxyphenyl, benzyl and benzoyl group semicarbazide derivatives 2b-2g were obtained (Scheme I). The reaction medium was diethyl ether (at room temperature) or both substrates were heated at the melt for 10 h. Compound 2a was obtained by Roman et al 16 When we used cyclohexyl or 1-phenylethyl isocyanate, the reaction led to new derivatives 3h and 3i with containing cyclohexyl or 1-phenylethyl group at the position 4 of the formed 1,2,4-triazol-5-one ring (Scheme I).…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and Antibacterial Evaluation of Some Semicarbazides and 1,2,4‐Triazol‐5‐Ones Containing Thiophene Moieties

Pitucha

Olender

Wujec

et al. 2010

J Chinese Chemical Soc

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In this study, some 3-(thiophen-2-ylmethyl)-4-substituted-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives were synthesized by the cyclization reaction of 1-(thiophen-2-ylacetyl)-4-substituted semicarbazide derivatives in alkaline medium or in the immediate reaction of thiophen-2-yl-acetic acid hydrazide with isocyanates. The structures of all new compounds were confirmed by analytical and spectroscopic methods. Selected derivatives were evaluated in vitro against several species of aerobic bacteria. Some of them showed activity against S. pyogenes, P. aeruginosa and S. aureus.

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“…The compound 3a was obtained the same method. 17 The structure of new obtained compounds was confirmed by elemental analysis as well as IR and 1 H NMR spectra.…”

Section: Resultsmentioning

confidence: 80%

Section: Resultsmentioning

confidence: 99%

Synthesis and Antibacterial Evaluation of Some Semicarbazides and 1,2,4‐Triazol‐5‐Ones Containing Thiophene Moieties

Pitucha

Olender

Wujec

et al. 2010

J Chinese Chemical Soc

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“…The required starting material (4) was obtained through the ring closure reaction of potassium 2-(2-(thiophen-2-yl)acetyl)hydrazine-1carbodithioate (3) 32 with excess hydrazine hydrate in water ( Figure 2). As shown by NMR, the isolated crude material was sufficiently pure, and was used as such in the next step, although the analytical sample was purified by recrystallization prior to structural investigation.…”

Section: Resultsmentioning

confidence: 99%

“…For example, reaction of 4-amino-3-mercapto-1,2,4-triazoles with a variety of reagents has been extensively employed for the generation of triazolothiadiazines, 27 whose interesting biological activities have been well documented. 28 The present contribution aims at expanding the series of previously reported derivatives of 5-(thiophen-2-ylmethyl)-2,4-dihydro-3H-1,2,4triazole-3-thione 29,30 by preparing several azomethines and triazolothiadiazines derived from the aforementioned scaffold featuring an amino group at position 4 of the triazole ring. Further structural modification (e.g.…”

Section: Introductionmentioning

confidence: 99%

Schiff Bases and Triazolothiadiazines Derived from A Thiophene-Substituted 4-Amino-3-Mercapto-1,2,4-Triazole

Roman¹

2019

Acta Chemica Iasi

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4-Amino-5-(thiophen-2-ylmethyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione was synthesized and converted into the corresponding Schiff bases using several aromatic aldehydes. Reaction of this aminotriazolethione with phenacyl bromides lead to triazolothiadiazines, which were subsequently reduced with NaBH4 to dihydrotriazolothiadiazines. The latter type of fused heterocycle has been also obtained directly by reacting one of the previously obtained Schiff base with phenacyl bromides. NMR analysis confirmed the structures of the synthesized compounds.

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“…A search of the literature revealed essentially no examples of direct condensations to provide the desired N 2 -alkylated N 4 -unsubstituted triazolones from acyl semicarbazides with the substitution pattern shown. The reported base-promoted triazolone-forming reactions (using hydroxide as base) have all employed acyl semicarbazide precursors containing latent N 4 -triazolone substitution. , A single reference employing a combination of triflic acid and hexamethyldisilazide provided the only encouraging precedent …”

Section: Resultsmentioning

confidence: 99%

A Convergent Kilogram-Scale Synthesis of the PPARα Agonist LY518674: Discovery of a Novel Acid-Mediated Triazolone Synthesis

Braden

Coffey

Doecke

et al. 2007

Org. Process Res. Dev.

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The first kilogram-scale synthesis of the PPARr agonist LY518674 (1) is described. The de novo convergent synthetic approach involved coupling of two rapidly assembled components, triazolone formation via a novel acid-promoted cyclization reaction, and final step saponification, delivering the compound in 32.5% overall yield via eight total steps with a six-step longest linear sequence. A regioselective alkylation on the dianion of 4-hydroxyphenylbutyric acid allowed the direct preparation of one of the convergent coupling partners, carboxylic acid 12, and an unusual solvent effect enabled the installation of a urea group on a protected hydrazine, permitting the regiospecific preparation of the other coupling partner, semicarbazide mesylate 17. Sulfonic acids were found to effect the desired triazolone ring formation, affording 25 from the coupled precursor acyl semicarbazide 23. Following saponification of 25 to 1, a wide solubility differential between ethyl acetate extracts of 1 and solutions of 1 in anhydrous ethyl acetate was harnessed in the final crystallization step to deliver the final compound in high yield and purity. The novel acidmediated triazolone formation was further evaluated on a range of additional substrates, showing the new methodology to be largely complementary to existing base-mediated triazolone syntheses.

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Organic Sulfur Compounds. Vi. 5-(2-Thienylmethyl)-1,2,4-Triazole Derivatives

Cited by 3 publications

References 11 publications

Synthesis and Antibacterial Evaluation of Some Semicarbazides and 1,2,4‐Triazol‐5‐Ones Containing Thiophene Moieties

Synthesis and Antibacterial Evaluation of Some Semicarbazides and 1,2,4‐Triazol‐5‐Ones Containing Thiophene Moieties

Schiff Bases and Triazolothiadiazines Derived from A Thiophene-Substituted 4-Amino-3-Mercapto-1,2,4-Triazole

A Convergent Kilogram-Scale Synthesis of the PPARα Agonist LY518674: Discovery of a Novel Acid-Mediated Triazolone Synthesis

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