Novel Method for the peri Annelation of a Thiophene Ring to 1H-perimidine and 1,2,3-triazaphenalene Derivatives

Shcherbakov, S. V.; Lobach, D. A.; Аксенов, А. В.

doi:10.1007/s10593-014-1476-5

Cited by 8 publications

(7 citation statements)

References 7 publications

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“…The electrolysis was performed for 4 h at the potential of 1.35 V. The starting compounds 1а-с,g were obtained according to a published procedure [17], 1d-f -by another procedure [18]. The physicochemical properties of compound 1а were identical to published data [17], those of compounds 1b,c -to the data given in [14], compounds 1d-f -to the data in [18]. …”

Section: Methodsmentioning

confidence: 81%

“…IR spectrum, ν, cm -1 : 3057 (С-Н), 1595 (С=N), 690 (thiophene). The 1 H and 13 С NMR spectra were identical to the literature reference [14].…”

Section: Preparation Of 1-thia-57-diazacyclopenta[cd]phenalenes 2a-gmentioning

confidence: 87%

“…Based on the previously developed methods for thiolation of 2,3'-biquinolyl derivatives [12,13], using either elemental sulfur alone or sulfur in the presence of alkali, we decided to apply the same system also for the thiolation of carbonyl compounds. Refluxing of 1H-perimidine and 1,2,3-triazaphenalene carbonyl derivatives with elemental sulfur in DMSO in the presence of KОН led to the synthesis of both previously known, as well as new 1-thia-5,7-diazacyclopenta[cd]phenalenes [14]. The same method was used for preparing the first representative of a new heterocyclic system, 2-phenyl-1-thia-5,6,7-triazacyclopenta[cd]phenalene [14].…”

Section: _______mentioning

confidence: 99%

“…Refluxing of 1H-perimidine and 1,2,3-triazaphenalene carbonyl derivatives with elemental sulfur in DMSO in the presence of KОН led to the synthesis of both previously known, as well as new 1-thia-5,7-diazacyclopenta[cd]phenalenes [14]. The same method was used for preparing the first representative of a new heterocyclic system, 2-phenyl-1-thia-5,6,7-triazacyclopenta[cd]phenalene [14]. Unfortunately, the reaction could not be repeated with acetyl derivatives.…”

Section: _______mentioning

confidence: 99%

“…Yield 0.25 g (86%). Mp 195-197°C (1:1 petroleum ether-benzene) (mp 195-197°C [14] (1:1 petroleum ether-benzene)). A sample mixed with an authentic sample did not exhibit melting point depression.…”

Section: Preparation Of 1-thia-57-diazacyclopenta[cd]phenalenes 2a-gmentioning

confidence: 99%

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Synthesis of 1-Thia-5,7-Diazacyclopenta[cd]- Phenalenes from 6(7)-Derivatives of Perimidine

Аксенов

Shcherbakov

Lobach

et al. 2014

Chem Heterocycl Comp

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Electrochemical oxidation of 6(7)-benzoylperimidines was shown to involve two stages of single electron transfer. Based on cyclic voltammetry and microelectrolysis data, a synthetic method was developed for the peri annelation of thiophene ring to benzoyl derivatives of perimidine. A new method was proposed for the preparation of 1-thia-5,7-diazacyclopenta[cd]phenalenes by fusing 6(7)-carbonyl derivatives of perimidine with elemental sulfur.Thiophenes and condensed heterocyclic derivatives of thiophenes are structural elements in many biologically active compounds [1] and potential drugs [2]. Besides that, thiophene derivatives represent useful building blocks for chemical synthesis [3].We have previously developed a method for the peri annelation of thiophene nucleus to 1Н-perimidine derivatives, based on benzoylation of perimidine-6(7)-thiols with benzoic acid in polyphosphoric acid [4]. This method was successfully used for preparing the first two derivatives of the previously unknown 1-thia-5,7-diazacyclopenta[cd]phenalene heterocyclic system.Many of the reactions involving elemental sulfur occur by free radical mechanism [5-8], therefore in the first part of our work we studied the electrochemical oxidation and reduction of 6(7)-benzoylperimidines. Taking into account the high reactivity of radical ion intermediates in the synthesis of sulfur derivatives [9, 10], we considered the possible cyclization of 1H-perimidine carbonyl derivatives with the participation of hydrogen sulfide under the conditions of radical ion initiation at room temperature.The starting substrates for this work were the benzoylperimidines 1а-с. A cyclic voltammetry investigation of these compounds (Table 1, Fig. 1) revealed two stages of electrochemical single-electron oxidation. The first quasi-reversible stage at the potential of Е = 0.72-0.75 V involved the formation of unstable radical cation, which underwent further single-electron oxidation (Е = 1.52-1.62 V), followed by deprotonation. The lack of a proton peak in the cathode segment of the cyclic voltammetry curve indicated the absence of free protons in the solution due to the likely protonation of either the starting compound or alkaline impurities in the solvent.

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Section: Methodsmentioning

confidence: 81%

“…IR spectrum, ν, cm -1 : 3057 (С-Н), 1595 (С=N), 690 (thiophene). The 1 H and 13 С NMR spectra were identical to the literature reference [14].…”

Section: Preparation Of 1-thia-57-diazacyclopenta[cd]phenalenes 2a-gmentioning

confidence: 87%

Section: _______mentioning

confidence: 99%

Section: _______mentioning

confidence: 99%

Section: Preparation Of 1-thia-57-diazacyclopenta[cd]phenalenes 2a-gmentioning

confidence: 99%

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Synthesis of 1-Thia-5,7-Diazacyclopenta[cd]- Phenalenes from 6(7)-Derivatives of Perimidine

Аксенов

Shcherbakov

Lobach

et al. 2014

Chem Heterocycl Comp

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Recent Advances in Organic Reactions Involving Elemental Sulfur

2017

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Elemental sulfur hasb een known since Antiquity and found widespread applications in the preparation of black gunpowder,t he synthesis of sulfuric acid as well as other sulfur-containing compounds,a nd the vulcanization of rubber.O ver the last several years,wehave come to better understand its properties andd iscover more applications of elementals ulfuri ns ynthetic organic chemistry.T his review summarizes the advancesf rom 2000i nt he construction of organic molecules using elemental sulfur via sulfuration, oxidation, reduction and redox condensation processes.

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ChemInform Abstract: Novel Method for the peri Anellation of a Thiophene Ring to 1H‐Perimidine and 1,2,3‐Triazaphenalene Derivatives.

2014

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Novel Method for the peri Annelation of a Thiophene Ring to 1H-perimidine and 1,2,3-triazaphenalene Derivatives

Cited by 8 publications

References 7 publications

Synthesis of 1-Thia-5,7-Diazacyclopenta[cd]- Phenalenes from 6(7)-Derivatives of Perimidine

Synthesis of 1-Thia-5,7-Diazacyclopenta[cd]- Phenalenes from 6(7)-Derivatives of Perimidine

Recent Advances in Organic Reactions Involving Elemental Sulfur

ChemInform Abstract: Novel Method for the peri Anellation of a Thiophene Ring to 1H‐Perimidine and 1,2,3‐Triazaphenalene Derivatives.

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