Heteroatom Chemistry最新文献

{"title":"Synthesis, Antimicrobial Properties, and Inhibition of Catalase Activity of 1,4-Naphtho- and Benzoquinone Derivatives Containing N-, S-, O-Substituted","authors":"Semih Kurban, N. Deniz, C. Sayil, Mustafa Ozyurek, Kubilay Guclu, M. Stasevych, V. Zvarych, Olena Komarovska-Porokhnyavet, V. Novikov","doi":"10.1155/2019/1658417","DOIUrl":"https://doi.org/10.1155/2019/1658417","url":null,"abstract":"A series of new 1,4-naphtho- and benzoquinone derivatives possessing N-, S-, O-substituted groups which has not been reported yet has been synthesized from 2,3-dichloro-1,4-naphthoquinone 1 and 2,3,5,6-tetrachlorocyclohexa-2,5-diene-1,4-dione 15 involving a Michael addition. In the synthesized compounds, antimicrobial activity at low concentrations against Escherichia coli B-906, Staphylococcus aureus 209-P, and Mycobacterium luteum B-917 bacteria and Candida tenuis VKM Y-70 and Aspergillus niger F-1119 fungi in comparison with controls was identified. 2-Chloro-3-((2-(piperidin-1-yl)ethyl)amino)naphthalene-1,4-dione 3g and 2,5-dichloro-3-ethoxy-6-((2,4,6-trifluorophenyl)amino)cyclohexa-2,5-diene-1,4-dione 17 were the most potent, with a minimum inhibitory concentration value of 15.6 μg/mL against test-culture M. luteum and S. aureus, respectively. Furthermore, in this work, a catalase activity of benzo- and naphthoquinone derivatives was examined for the first time. The catalase activity of benzo- and naphthoquinone derivatives was determined, showing that compound 3g had significant inhibition activity for catalase enzyme.","PeriodicalId":12816,"journal":{"name":"Heteroatom Chemistry","volume":" ","pages":""},"PeriodicalIF":0.3,"publicationDate":"2019-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1155/2019/1658417","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47015219","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"An Efficient Selectfluor-Mediated Oxidative Thio- and Selenocyanation of Diversely Substituted Indoles and Carbazoles","authors":"R. Abonía, Luisa F. Gutiérrez, Angela T Zwarycz, Sebastian J Correa Smits, K. Laali","doi":"10.1155/2019/1459681","DOIUrl":"https://doi.org/10.1155/2019/1459681","url":null,"abstract":"A facile Selectfluor-mediated oxidative method for direct introduction of SCN and SeCN groups into diversely substituted indoles and carbazoles is described, by employing readily available thiocyanate and selenocyanate salts, and the scope of the method is underscored by providing 24 examples. The feasibility to sequentially introduce SCN followed by SeCN on a carbazole framework and to synthesize the corresponding S-tetrazole and Se-tetrazole derivatives is also demonstrated.","PeriodicalId":12816,"journal":{"name":"Heteroatom Chemistry","volume":" ","pages":""},"PeriodicalIF":0.3,"publicationDate":"2019-01-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1155/2019/1459681","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46345845","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Alkoxy(tetraaryl)silicates bearing 9,10-disilatriptycene skeleton","authors":"Shintaro Ishida,&nbsp;Minori Takiguchi,&nbsp;Takeaki Iwamoto","doi":"10.1002/hc.21481","DOIUrl":"10.1002/hc.21481","url":null,"abstract":"<p>As anionic five-coordinate silicon species (five-coordinate silicates) exhibit high reactivity and unique fluxional behavior, their structure and property have received substantial attention. We report herein synthesis, structure, and fluxional behavior of alkoxy(tetraaryl)silicates having the 9,10-disilatriptycene skeleton (<b>6</b>⁻ and <b>7</b>⁻). The molecular structure of the cryptate salt [Li(crypt-222)]⁺<b>7</b>⁻ shows that the five-coordinate silicon adopts a distorted trigonal bipyramidal structure with oxygen atom occupying an equatorial position. In the ¹H and ¹³C{¹H} NMR spectra of [Li(crypt-222)]⁺<b>7</b>⁻, a set of signals due to <i>o</i>-phenylene blades in <b>7</b>⁻ was observed at room temperature, which indicates fluxional behavior of <b>7</b>⁻ on the NMR timescale. Computational study suggests that the observed process proceeds via a 120° rotation of bidentate ligand around the Si-Si axis that consists of two sequential Berry pseudorotations.</p>","PeriodicalId":12816,"journal":{"name":"Heteroatom Chemistry","volume":"29 5-6","pages":""},"PeriodicalIF":0.3,"publicationDate":"2018-12-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/hc.21481","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44861034","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":"Heteroatom effects toward isomerization of intermediates in Wittig reactions of non-stabilized phosphonium ylides bearing a phosphaheteratriptycene skeleton with benzaldehyde","authors":"Yosuke Uchiyama,&nbsp;Suguru Kuniya,&nbsp;Ryo Watanabe,&nbsp;Takemaru Ohtsuki","doi":"10.1002/hc.21473","DOIUrl":"10.1002/hc.21473","url":null,"abstract":"<p>Isomerization of intermediates, <i>cis</i>- and <i>trans</i>-1,2-oxaphosphetanes, in Wittig reactions of non-stabilized phosphonium ylides bearing a phosphaheteratriptycene skeleton containing group 14 (PhSi, PhGe, PhSn, <i>n</i>-BuSn) and 15 (P, As, Sb, and Bi) elements with benzaldehyde (PhCHO) was investigated by variable-temperature (VT)³¹P{¹H} NMR spectroscopy. The isomerization from the <i>cis</i>-1,2-oxaphosphetane to the <i>trans</i>-form occurred at lower temperatures as the row number of the same group elements increases. Wittig reactions under the same conditions gave the (<i>Z</i>)-olefin as a major product in the cases of period 3 elements (PhSi and P) and the (<i>E</i>)-olefin as a major product in the cases of elements from period 4 and below (PhGe, PhSn, <i>n</i>-BuSn, As, Sb, and Bi). The selectivity of olefin formation is considered to depend on the isomerization temperature of the intermediates, because each olefin must be obtained from the corresponding 1,2-oxaphosphetane. The VT-³¹P{¹H} NMR spectra showed that the <i>cis</i>-1,2-oxaphosphetanes were the kinetic products in the first step of Wittig reactions and the <i>trans</i>-forms were the thermodynamically stable products formed by isomerization from the <i>cis</i>-forms via ring-opening and ring-closing reactions of phosphonium ylides with PhCHO. Density functional theory (DFT) calculations indicated that <i>cis</i>-1,2-oxaphosphetanes were less stable than the <i>trans</i>-forms by ~2 kcal/mol, supporting thermodynamically favorable isomerization from <i>cis</i>-forms to <i>trans</i>-forms, as observed by VT-³¹P{¹H} NMR spectroscopy. Heteroatoms at the bridgehead position of the phosphaheteratriptycene skeleton significantly affected the isomerization temperature as well as the phosphorus-31 signals in the ³¹P{¹H} NMR spectra, which were observed at lower field as row number of the same group element increases.</p>","PeriodicalId":12816,"journal":{"name":"Heteroatom Chemistry","volume":"29 5-6","pages":""},"PeriodicalIF":0.3,"publicationDate":"2018-12-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/hc.21473","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42588541","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":"Dibromometallyl-iron complexes generated by the recombination of an alumanyl-iron complex with EBr3 (E = Al, Ga)","authors":"Tatsuya Yanagisawa,&nbsp;Yoshiyuki Mizuhata,&nbsp;Norihiro Tokitoh","doi":"10.1002/hc.21465","DOIUrl":"10.1002/hc.21465","url":null,"abstract":"<p>The first dibromoalumanyl-iron complex [Br₂Al–FeCp(CO)₂] was synthesized by the reaction of monobromoalumanyl-iron complex bearing a bulky substituent on aluminum atom with AlBr₃, whose structure was determined by the X-ray crystallographic analysis and the NMR measurement. The reactions monobromoalumanyl-iron complex with GaBr₃ show that these reactions would proceed by the mutual recombination of substituents.</p>","PeriodicalId":12816,"journal":{"name":"Heteroatom Chemistry","volume":"29 5-6","pages":""},"PeriodicalIF":0.3,"publicationDate":"2018-12-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/hc.21465","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42441984","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":"Oxidative addition of (RO)2P(O)H to Pt(0) complexes generating Pt-H complexes: P(O)-H bond cleavage vs P(O-H) bond cleavage","authors":"Tieqiao Chen,&nbsp;Li-Biao Han","doi":"10.1002/hc.21460","DOIUrl":"10.1002/hc.21460","url":null,"abstract":"<p>(MeO)₂P(O)H oxidatively added to Pt(PCy₃)₂ quickly, at the beginning, generating <i>cis</i>-Pt-H[P(O)(OMe)₂](PCy₃)₂ predominately, which gradually isomerized to <i>trans</i>-Pt-H[P(O)(OMe)₂](PCy₃)₂. In contrast, a (MeO)₂P(OH)-coordinated Pt complex in situ generated only produced <i>trans</i>-Pt-H[P(O)(OMe)₂](PCy₃)₂. These results showed that the P(O)-H bond perhaps directly adds to Pt(0) complex (P(O)-H cleavage) forming Pt-H complexes, rather than by an alternative coordination of (MeO)₂P(OH) to Pt(0) followed by an O-H cleavage path.</p>","PeriodicalId":12816,"journal":{"name":"Heteroatom Chemistry","volume":"29 5-6","pages":""},"PeriodicalIF":0.3,"publicationDate":"2018-12-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/hc.21460","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46893533","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":"Uniquely folded shapes, photophysical properties, and recognition abilities of macrocyclic BODIPY oligomers","authors":"Tomohiro Hojo,&nbsp;Takashi Nakamura,&nbsp;Ryota Matsuoka,&nbsp;Tatsuya Nabeshima","doi":"10.1002/hc.21470","DOIUrl":"10.1002/hc.21470","url":null,"abstract":"<p>Macrocyclic BODIPY/dipyrrin tetramers and pentamers connected by <i>m</i>-phenylene linkers were synthesized. Their uniquely folded shapes were revealed by a single-crystal X-ray diffraction analysis, and their dynamic structural behaviors in solution were investigated by variable-temperature NMR measurements. The BODIPY oligomers exhibited strong emission properties without quenching. Furthermore, the BODIPY pentamer interacted with an ammonium cation utilizing the negatively charged binding pockets in which the polarized B^δ+–F^δ− bonds are present.</p>","PeriodicalId":12816,"journal":{"name":"Heteroatom Chemistry","volume":"29 5-6","pages":""},"PeriodicalIF":0.3,"publicationDate":"2018-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/hc.21470","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48489731","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":"Preparation and reactivity of benzo-1,2-dichalcogenete derivatives and their bis(triphenylphosphine)platinum complexes","authors":"Takeshi Kimura,&nbsp;Tsukasa Nakahodo,&nbsp;Hisashi Fujihara","doi":"10.1002/hc.21472","DOIUrl":"10.1002/hc.21472","url":null,"abstract":"<p>The reaction of 4,5-(<i>o</i>-xylylenedichalcogeno)-3,6-dialkylphthalonitrile (<b>1a</b>-<b>d</b>) with aluminum chloride in toluene gave ring-opened products, 3,6-dialkyl-4,5-dicyanobenzene-1,2-dithiols (<b>2a</b>,<b>b</b>), for sulfur derivatives and cyclized products, 3,6-dialkyl-4-,5-dicyanobenzo-1,2-diselenetes (<b>2c</b>,<b>d</b>), for selenium derivatives. Asymmetrically substituted 3,6-diethylbenzo-1,2-diselenete (<b>2e</b>) with a bromo and a nitrile group was prepared by the reaction of 4,5-(<i>o</i>-xylylenediseleno)-3,6-diethyl-2-cyano-1-bromobenzene (<b>1e</b>) with aluminum chloride in toluene. Compound <b>2e</b> was unstable compared with <b>2c</b> and produced an equilibrium mixture of <b>2e</b> and dimerized dibenzotetraselenocin <b>3e</b> in the chloroform solution. Compound <b>2c</b> was reacted with methyl iodide in the presence of sodium hydroxide to produce 1,2-bis(methylseleno)-3,6-diethyl-4,5-dicyanobenzene (<b>4</b>) and bis(2-methylseleno-3,6-diethyl-4,5-dicyanophenyl)diselenide (<b>5</b>). Compounds <b>2a</b> and <b>2c</b> were reacted with tetrakis(triphenylphosphine)platinum in toluene to give the corresponding platinum complexes <b>6a</b> and <b>6c</b> with a dichalcogenaplatinumole ring, respectively. The structures of <b>6a</b> and <b>6c</b> were determined by NMR, MS, and X-ray crystallography. To obtain theoretical information, the structures of dichalcogenetes <b>2a′</b>,<b> 2c</b>,<b> 2e</b>,<b> 2f</b>,<b> 2g</b> and platinum complexes <b>6a</b> and <b>6c</b> were optimized by the DFT method using the Gaussian 09 program and their HOMO and LUMO energy levels were calculated by time-dependent density functional theory.</p>","PeriodicalId":12816,"journal":{"name":"Heteroatom Chemistry","volume":"29 5-6","pages":""},"PeriodicalIF":0.3,"publicationDate":"2018-12-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/hc.21472","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"47067674","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":"Photoreactions of Sc3N@Ih-C80 and Lu3N@Ih-C80 with disilirane: Isolation and characterization of labile 1,2-adducts","authors":"Masahiro Kako,&nbsp;Fumiaki Ozeki,&nbsp;Shinji Kanzawa,&nbsp;Shinpei Fukazawa,&nbsp;Kumiko Sato,&nbsp;Michio Yamada,&nbsp;Yutaka Maeda,&nbsp;Makoto Furukawa,&nbsp;Takeshi Akasaka","doi":"10.1002/hc.21477","DOIUrl":"10.1002/hc.21477","url":null,"abstract":"<p>The photolysis of Sc₃N@<i>I</i>_<i>h</i>-C₈₀ with disilirane (1,2-disilacyclopropane) afforded the corresponding 1,2- and 1,4-adducts. The relatively unstable 1,2-product was characterized using spectroscopic and electrochemical analyses, and theoretical calculations. The relative energies of the optimized structures are consistent with the experimentally observed isomerization of the 1,2-adduct to the 1,4-adduct. The electron-donating effects of the silyl groups in these products were confirmed by comparing the redox potentials of the related Sc₃N@<i>I</i>_<i>h</i>-C₈₀ derivatives. The relative stabilities and electronic properties of the 1,2- and 1,4-adducts of Lu₃N@<i>I</i>_<i>h</i>-C₈₀ show similar aspects to those obtained for the corresponding Sc₃N@<i>I</i>_<i>h</i>-C₈₀ derivatives.</p>","PeriodicalId":12816,"journal":{"name":"Heteroatom Chemistry","volume":"29 5-6","pages":""},"PeriodicalIF":0.3,"publicationDate":"2018-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/hc.21477","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44930093","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 green and mild procedure to selective synthesis of diarylamine via domino reaction of aryl halides and arginine catalyzed by magnetic-MOF","authors":"Mohammad Soleiman-Beigi,&nbsp;Fariba Mohammadi","doi":"10.1002/hc.21450","DOIUrl":"10.1002/hc.21450","url":null,"abstract":"<p>Efficient and selective direct synthesis of diarylamines from aryl halides and arginine as a nitrogen-donor reagent is reported. Arginine, which is an oral supplement, acts as a useful nitrogen source donor in the copper-catalyzed reaction. Fe₃O₄/Cu₃(BTC)₂, which was easily separated and recycled with a magnet, improved the rate and facilitation of the synthesis of diarylamines selectively. The introduction of a new and available N-source, simple magnetic separation process, normal atmospheric conditions, and excellent yields under mild reaction conditions are other important features of this work.</p>","PeriodicalId":12816,"journal":{"name":"Heteroatom Chemistry","volume":"29 4","pages":""},"PeriodicalIF":0.3,"publicationDate":"2018-12-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1002/hc.21450","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"45338457","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}