Reena Kaushik, Mahesh Chand, Mohd. Rashid, Subhash C. Jain
{"title":"Synthesis of novel 2-acetamidothiazoles tethered with 1,2,3-triazole and pyridine pharmacophores","authors":"Reena Kaushik, Mahesh Chand, Mohd. Rashid, Subhash C. Jain","doi":"10.1002/hc.21447","DOIUrl":"10.1002/hc.21447","url":null,"abstract":"<p>A novel series of 2-acetamidothiazoles bearing 1,2,3-triazole and pyridine moieties were designed and synthesized using simple chemical methodology. 3-Amino pyridine was converted into a potent intermediate 2-chloro-<i>N</i>-(4-(5-methyl-1-(pyridin-3-yl)-1H-1,2,3-triazol-4-yl)thiazol-2-yl)acetamide (<b>5</b>) in four steps using molecular modification approach. Heterocyclic amine(s)/ heterocyclic and aromatic thiol(s) were then introduced in <b>5</b> to obtain target compounds <b>6a-6i</b>. In all, we have synthesized eleven novel molecules which have the flavor of each of these heterocyclic moieties, viz. pyridine, 1,2,3-triazole, 2-acetamido-thiazole, heterocyclic amine(s)/ heterocyclic and aromatic thiol(s). The presence of each of these bioactive moieties in a single molecular frame could be beneficial to the development of new drug candidate because these moieties together contribute to the overall resultant biological activity of the target hybrid molecule. Structure elucidation of all the newly synthesized compounds was established using IR, <sup>1</sup>H, <sup>13</sup>C NMR, mass spectrometry along with their elemental analyses.</p>","PeriodicalId":12816,"journal":{"name":"Heteroatom Chemistry","volume":"29 4","pages":""},"PeriodicalIF":0.3,"publicationDate":"2018-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/hc.21447","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43973597","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Hassan Abul-Futouh, Mohammad El-khateeb, Helmar Görls, Wolfgang Weigand
{"title":"[FeFe]-hydrogenase H-cluster mimics mediated by mixed (S, Se) and (S, Te) bridging moieties: Insight into molecular structures and electrochemical characteristics","authors":"Hassan Abul-Futouh, Mohammad El-khateeb, Helmar Görls, Wolfgang Weigand","doi":"10.1002/hc.21446","DOIUrl":"10.1002/hc.21446","url":null,"abstract":"<p>Two synthetic models of the active site of [FeFe]-hydrogenase containing mixed (S, Se) and (S, Te) bridges have been synthesized and characterized. These complexes [Fe<sub>2</sub>(CO)<sub>6</sub>{μ-S(CH<sub>2</sub>)<sub>4</sub>E-μ)}] (E = Se (<b>1</b>), Te (<b>2</b>)) are obtained in moderate yields from the reaction of Fe<sub>3</sub>(CO)<sub>12</sub> with 1,2-thiaselenane or 1,2-thiatellurane. They have been characterized by spectroscopic techniques (IR, <sup>1</sup>H-, <sup>13</sup>C{<sup>1</sup>H}-, <sup>77</sup>Se{<sup>1</sup>H}-, <sup>125</sup>Te{<sup>1</sup>H}-NMR, and MS) and elemental analysis. The structures of [Fe<sub>2</sub>(CO)<sub>6</sub>{μ-S(CH<sub>2</sub>)<sub>4</sub>Se-μ)}] and [Fe<sub>2</sub>(CO)<sub>6</sub>{μ-S(CH<sub>2</sub>)<sub>4</sub>Te-μ)}] are determined by X-ray structure determination and show the expected butterfly geometry. Moreover, the influence of the mixed chalcogen atoms on the redox properties and the catalytic behavior of <b>1</b> and <b>2</b> are studied using cyclic voltammetry.</p>","PeriodicalId":12816,"journal":{"name":"Heteroatom Chemistry","volume":"29 5-6","pages":""},"PeriodicalIF":0.3,"publicationDate":"2018-10-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/hc.21446","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43959379","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Anastasiya I. Govdi, Sergey F. Vasilevsky, Svetlana F. Malysheva, Olga N. Kazheva, Oleg A. Dyachenko, Vladimir A. Kuimov
{"title":"Tri(1-naphthyl)phosphine as a ligand in palladium-free Sonogashira cross-coupling of arylhalogenides with acetylenes","authors":"Anastasiya I. Govdi, Sergey F. Vasilevsky, Svetlana F. Malysheva, Olga N. Kazheva, Oleg A. Dyachenko, Vladimir A. Kuimov","doi":"10.1002/hc.21443","DOIUrl":"10.1002/hc.21443","url":null,"abstract":"<p>Tri(1-naphthyl)phosphine (Np<sub>3</sub>P) has been easily prepared in 34% yield from red phosphorus and 1-bromonaphthalene in the superbasic system <i>t</i>-BuONa/DMSO. The expedient procedures for the synthesis of aryl acetylenes by Sonogashira coupling of aryl iodides with terminal alkynes using Np<sub>3</sub>P as a ligand have been developed. For the first time, it is found that the reaction with compounds containing electron-donating substituents preferably affords buta-1,3-diynes.</p>","PeriodicalId":12816,"journal":{"name":"Heteroatom Chemistry","volume":"29 4","pages":""},"PeriodicalIF":0.3,"publicationDate":"2018-10-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/hc.21443","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47399128","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"A tribute to Professor Naomichi Furukawa on the occasion of his 82nd birthday","authors":"Satoshi Ogawa, Akihiko Ishii, Derek P. Gates","doi":"10.1002/hc.21442","DOIUrl":"10.1002/hc.21442","url":null,"abstract":"","PeriodicalId":12816,"journal":{"name":"Heteroatom Chemistry","volume":"29 5-6","pages":""},"PeriodicalIF":0.3,"publicationDate":"2018-10-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/hc.21442","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44536144","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"A theoretical study of the properties of ninety-two “aromatic” six-membered rings including benzene, azines, phosphinines and azaphosphinines","authors":"Eric Elguero, Ibon Alkorta, José Elguero","doi":"10.1002/hc.21441","DOIUrl":"10.1002/hc.21441","url":null,"abstract":"<p>Ninety-two unsaturated hexagonal compounds (from benzene to hexaphosphinine, including azines and azaphosphinines) have been theoretically studied at DFT level, B3LYP/6-311++G(d,p). Lone pair/lone pair repulsion between adjacent N atoms has been deduced using an empirical partition of the energy. Aromaticity based on magnetic criteria and on Bader analysis was studied finding that both criteria were almost orthogonal. The structure that are nonplanar or broken have been analyzed in function of their geometry or the fragments, respectively.</p>","PeriodicalId":12816,"journal":{"name":"Heteroatom Chemistry","volume":"29 4","pages":""},"PeriodicalIF":0.3,"publicationDate":"2018-10-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/hc.21441","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44083016","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
{"title":"Synthesis of 2,2-diarylvinyl phenyl selenides by dehydration of 2-hydroxyalkyl phenyl selenides","authors":"Nicolai Stuhr-Hansen","doi":"10.1002/hc.21438","DOIUrl":"10.1002/hc.21438","url":null,"abstract":"<p>A novel route to 2,2-diarylvinyl phenyl selenides is reported by dehydration of the corresponding 2,2-diaryl-2-hydroxyethyl phenyl selenides, prepared by oxyphenylselenenylations of the corresponding 1,1-diarylethylenes, upon treatment with <i>p</i>-toluenesulfonic acid.</p>","PeriodicalId":12816,"journal":{"name":"Heteroatom Chemistry","volume":"29 4","pages":""},"PeriodicalIF":0.3,"publicationDate":"2018-10-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/hc.21438","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42110256","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Kerim Serbest, Özge Göktekin, Kaan Karaoğlu, Ali Zengin, Ufuk Çoruh
{"title":"Oxime derivative unsymmetrical azine, its Ni(II), Cu(II) and Zn(II) complexes: Synthesis, spectroscopy and catecholase activity","authors":"Kerim Serbest, Özge Göktekin, Kaan Karaoğlu, Ali Zengin, Ufuk Çoruh","doi":"10.1002/hc.21439","DOIUrl":"10.1002/hc.21439","url":null,"abstract":"<p>1-[(Z)-{(2E)-[(3E)-3-(hydroxyimino)butan-lidene]hydrazinylidene}methyl]naphthalen -2-ol, H2L (3) was synthesized by the agents of 2-hydroxy-1-naphtaldehyde, 2,3-butanedione monoxime and hydrazine in two steps. The structures of the compounds have been proposed by elemental analyses, spectroscopic data, that is, IR, <sup>1</sup>H NMR, UV-vis, X-ray, mass spectra (ESI or TOF), molar conductivities and magnetic susceptibility measurements. The ligand has potentially three nitrogens and an oxygen donor to be able to bind a metal center. In the light of analytical and physical results, it was suggested that the ligand may coordinate to by N,O/N2/N2O donor set to form square planar, octahedral, distorted square planar and tetrahedral complexes. Proton NMR evidence indicating that the ligand coordinates the metal ion through the phenolic oxygen and nitrogen of imine in the nickel and zinc complexes. Molar conductivity measurements reveal that all the complexes are non-electrolytes. In addition, catecholase activities of the complexes were studied. However, the only one of the complexes, <b>1b</b>, behaves as an effective catalyst toward oxidation of 3,5-di-tert-butylcatechol (3,5-DTBC) to its corresponding quinone derivative in MeOH saturated with O<sub>2</sub>. The reaction follows Michaelis-Menten enzymatic reaction kinetics with turnover numbers (kcat) 1.19 × 10<sup>3</sup>/hour.</p>","PeriodicalId":12816,"journal":{"name":"Heteroatom Chemistry","volume":"29 4","pages":""},"PeriodicalIF":0.3,"publicationDate":"2018-10-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/hc.21439","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42842926","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Nader Ghaffari Khaligh, Taraneh Mihankhah, Mohd Rafie Johan
{"title":"Efficient chemical fixation of CO2 into cyclic carbonates using poly(4-vinylpyridine) supported iodine as an eco-friendly and reusable heterogeneous catalyst","authors":"Nader Ghaffari Khaligh, Taraneh Mihankhah, Mohd Rafie Johan","doi":"10.1002/hc.21440","DOIUrl":"10.1002/hc.21440","url":null,"abstract":"<p>Green and sustainable synthesis is considered as a safer alternative to the conventional synthetic processes owing to its environmental friendly nature, atom economy, cost-effectiveness, and easy handling. Herein, the catalytic efficiency of poly(4-vinylpyridine) supported iodine (P4VP/I<sub>2</sub>) as a metal-free and organocatalyst system was studied and approved for an efficient chemical fixation of CO<sub>2</sub> into cyclic carbonates which is performed via the coupling of CO<sub>2</sub> with epoxides. The high conversion and excellent selectivity were obtained for a broad range of epoxides in the presence of catalytic amount of P4VP/I<sub>2</sub> under solvent-free conditions. The heterogeneous catalyst could be recovered and regenerated over several times with no significant loss of catalytic activity. The possible mechanism was described for the catalytic performance of P4VP/I<sub>2</sub> based on the synergetic effect of the Lewis acid and base sites and nucleophilic anion.</p>","PeriodicalId":12816,"journal":{"name":"Heteroatom Chemistry","volume":"29 4","pages":""},"PeriodicalIF":0.3,"publicationDate":"2018-10-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/hc.21440","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46882502","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Chandrabhan Verma, Dakeshwar K. Verma, Eno E. Ebenso, Mumtaz A. Quraishi
{"title":"Sulfur and phosphorus heteroatom-containing compounds as corrosion inhibitors: An overview","authors":"Chandrabhan Verma, Dakeshwar K. Verma, Eno E. Ebenso, Mumtaz A. Quraishi","doi":"10.1002/hc.21437","DOIUrl":"10.1002/hc.21437","url":null,"abstract":"<p>Use of organic compounds containing nitrogen (N), oxygen (O), sulfur (S), and phosphorus (P) heteroatoms in their molecular structures is one of the most effective, economic, and practical corrosion inhibitors. The effectiveness of the heteroatoms toward metallic corrosion inhibition follows the order: P > S > N > O. The metal-inhibitor interactions involve the charge sharing between the heteroatoms and empty d-orbitals of the surface metallic atoms; therefore, a heteroatom with lower electronegativity value is more potent to form strong bonding (charge sharing) with metallic surface as compared to more electronegative heteroatom. Literature study reveals that almost all corrosion inhibitors have either one or more heteroatoms in their molecular structures particularly in the form of polar functional groups, which enhance their adsorption tendency on metallic surface. Present review paper features the collection of some major works that have been published on metallic corrosion inhibition containing these P, S, O, and N heteroatoms. Since now, several review articles have been published describing the application of N and O atoms; however, the reviews on use of P and S heteroatoms are scare. Therefore, aim of the present article was to mainly describe the collection of corrosion inhibitors containing S and P heteroatoms.</p>","PeriodicalId":12816,"journal":{"name":"Heteroatom Chemistry","volume":"29 4","pages":""},"PeriodicalIF":0.3,"publicationDate":"2018-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/hc.21437","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47553898","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}
Zita Rádai, Petra Szeles, Nóra Zsuzsa Kiss, László Hegedűs, Tímea Windt, Veronika Nagy, György Keglevich
{"title":"Green synthesis and cytotoxic activity of dibenzyl α-hydroxyphosphonates and α-hydroxyphosphonic acids","authors":"Zita Rádai, Petra Szeles, Nóra Zsuzsa Kiss, László Hegedűs, Tímea Windt, Veronika Nagy, György Keglevich","doi":"10.1002/hc.21436","DOIUrl":"10.1002/hc.21436","url":null,"abstract":"<p>A series of dibenzyl α-hydroxyphosphonates and the corresponding α-hydroxyphosphonic acids, mostly new compounds, have been synthesized. The dibenzyl α-hydroxyphosphonates have been obtained in the Pudovik reaction of substituted benzaldehydes and dibenzyl phosphite in the presence of triethylamine as the catalyst. The amount of the solvent was minimized during the reaction, and the workup involved crystallization from the reaction mixture. A new protocol was developed to transform the dibenzyl 1-hydroxyphosphonates to the corresponding phosphonic acids by catalytic hydrogenation. The derivatives prepared were screened as potential cytotoxic agents against Mes-Sa human uterine sarcoma cell line.</p>","PeriodicalId":12816,"journal":{"name":"Heteroatom Chemistry","volume":"29 4","pages":""},"PeriodicalIF":0.3,"publicationDate":"2018-09-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/hc.21436","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43337199","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}