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Synthesis of 2-azido-4-chloro-6-phenylpyrimidine-5-carbaldehyde and its transformations in DMSO 2-azido-4-chloro-6-phenylpyrimidine-5-carbaldehyde 的合成及其在二甲基亚砜中的转化
IF 1.7 4区 化学
Russian Chemical Bulletin Pub Date : 2024-08-31 DOI: 10.1007/s11172-024-4321-8
N. V. Aleksandrova, E. B. Nikolaenkova, Yu. V. Gatilov, V. I. Mamatyuk, V. P. Krivopalov
{"title":"Synthesis of 2-azido-4-chloro-6-phenylpyrimidine-5-carbaldehyde and its transformations in DMSO","authors":"N. V. Aleksandrova,&nbsp;E. B. Nikolaenkova,&nbsp;Yu. V. Gatilov,&nbsp;V. I. Mamatyuk,&nbsp;V. P. Krivopalov","doi":"10.1007/s11172-024-4321-8","DOIUrl":"10.1007/s11172-024-4321-8","url":null,"abstract":"<div><p>2-Azido-4-chloro-6-phenylpyrimidine-5-carbaldehyde was synthesized by the Vilsmeier–Haack reaction. In DMSO, it transforms into 7-oxo-5-phenyl-4,7-dihydrotetrazolo[1,5-<i>a</i>]pyrimidine-6-carbaldehyde and then undergoes isomerization recyclization into 6-benzoyltetrazolo[1,5-<i>a</i>]pyrimidin-7(4<i>H</i>)-one. The structures of the obtained compounds were determined by NMR spectroscopy and X-ray diffraction.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 7","pages":"2014 - 2022"},"PeriodicalIF":1.7,"publicationDate":"2024-08-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142188999","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}
引用次数: 0
Stereo-dependent nucleophilic ring-opening of 1,6,10,14-tetraoxatetraspiro[2.1.25.1.29.1.213.13]hexadecane upon treatment with sodium azide 叠氮化钠处理 1,6,10,14-四氧杂螺[2.1.25.1.29.1.213.13]十六烷时的立体依赖性亲核开环反应
IF 1.7 4区 化学
Russian Chemical Bulletin Pub Date : 2024-08-31 DOI: 10.1007/s11172-024-4330-7
K. N. Sedenkova, D. V. Savchenkova, O. V. Ryzhikova, Yu. K. Grishin, E. B. Averina
{"title":"Stereo-dependent nucleophilic ring-opening of 1,6,10,14-tetraoxatetraspiro[2.1.25.1.29.1.213.13]hexadecane upon treatment with sodium azide","authors":"K. N. Sedenkova,&nbsp;D. V. Savchenkova,&nbsp;O. V. Ryzhikova,&nbsp;Yu. K. Grishin,&nbsp;E. B. Averina","doi":"10.1007/s11172-024-4330-7","DOIUrl":"10.1007/s11172-024-4330-7","url":null,"abstract":"<div><p>Nucleophilic ring-opening of 1,6,10,14-tetraoxatetraspiro[2.1.2<sup>5</sup>.1.2<sup>9</sup>.1.2<sup>13</sup>.1<sup>3</sup>]hexadecane, a cyclooctane structure spiro-fused with four oxirane fragments, under the action of sodium azide was studied. Depending on the relative configuration of stereocenters in the starting compound, the reaction proceeded as an intramolecular transannular cyclization with the formation of a 9-oxabicyclo[3.3.1]nonane skeleton or as an independent nucleophilic opening of the oxirane rings, leading to tetraazido tetraols of the cyclooctane series.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 7","pages":"2105 - 2109"},"PeriodicalIF":1.7,"publicationDate":"2024-08-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142189042","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}
引用次数: 0
2-(5-Phenyl-2H-tetrazol-2-yl)acetyl chloride as a key reagent in the synthesis of non-annulated polynuclear tetrazole-containing compounds with potential antidiabetic activity 将 2-(5-苯基-2H-四唑-2-基)乙酰氯作为合成具有潜在抗糖尿病活性的非annulated 多核四唑化合物的关键试剂
IF 1.7 4区 化学
Russian Chemical Bulletin Pub Date : 2024-08-31 DOI: 10.1007/s11172-024-4317-4
V. A. Ostrovskii, N. T. Shmaneva, I. S. Ershov, D. V. Antonenko, M. A. Skryl’nikova, A. V. Khramchikhin, E. N. Chernova, A. Yu. Grishina, N. A. Anisimova, S. M. Napalkova, O. V. Buyuklinskaya, V. S. Mazhai, Yu. N. Pavlyukova, R. E. Trifonov
{"title":"2-(5-Phenyl-2H-tetrazol-2-yl)acetyl chloride as a key reagent in the synthesis of non-annulated polynuclear tetrazole-containing compounds with potential antidiabetic activity","authors":"V. A. Ostrovskii,&nbsp;N. T. Shmaneva,&nbsp;I. S. Ershov,&nbsp;D. V. Antonenko,&nbsp;M. A. Skryl’nikova,&nbsp;A. V. Khramchikhin,&nbsp;E. N. Chernova,&nbsp;A. Yu. Grishina,&nbsp;N. A. Anisimova,&nbsp;S. M. Napalkova,&nbsp;O. V. Buyuklinskaya,&nbsp;V. S. Mazhai,&nbsp;Yu. N. Pavlyukova,&nbsp;R. E. Trifonov","doi":"10.1007/s11172-024-4317-4","DOIUrl":"10.1007/s11172-024-4317-4","url":null,"abstract":"<div><p>Non-annulated tetrazole-containing polynuclear compounds, in which heterocyclic fragments are bound by an acetamide linker were synthesized. The synthesis was accomplished by acylation of 2-hydrazinyl-4,6-dimethylpyrimidine, 4-amino-4<i>H</i>-1,2,4-triazol-3-thiol, 2-[(1-amino-1<i>H</i>-tetrazol-5-yl)thio]-<i>N-tert</i>-butylacetamide, 1-methyl-1<i>H</i>-tetrazol-5-amine, and 2-methyl-2<i>H</i>-tetrazol-5-amine with one key reagent, (5-phenyltetrazol-2-yl)acetyl chloride. Preliminary <i>in silico</i> studies showed the presence of the <i>in vivo</i> antidiabetic (diabetes 2 type) activity in <i>N′</i>-(4,6-dimethylpyrimidin-2-yl)-2-(5-phenyl-2<i>H</i>-tetrazol-2-yl)acetohydrazide. <i>N</i>-(3-Mercapto-4<i>H</i>-1,2,4-triazol-4-yl)-2-(5-phenyl-2<i>H</i>-tetrazol-2-yl)acetamide demonstrated minimal hypoglycemic activity in <i>in vivo</i> studies, at the same time, it showed pronounced activity as a drug for combating obesity.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 7","pages":"1977 - 1983"},"PeriodicalIF":1.7,"publicationDate":"2024-08-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142189260","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}
引用次数: 0
Modern electrosynthesis of spiro compounds 螺化合物的现代电合成
IF 1.7 4区 化学
Russian Chemical Bulletin Pub Date : 2024-08-31 DOI: 10.1007/s11172-024-4303-x
M. N. Elinson, Yu. E. Ryzhkova, F. V. Ryzhkov, V. M. Kalashnikova, M. P. Egorov
{"title":"Modern electrosynthesis of spiro compounds","authors":"M. N. Elinson,&nbsp;Yu. E. Ryzhkova,&nbsp;F. V. Ryzhkov,&nbsp;V. M. Kalashnikova,&nbsp;M. P. Egorov","doi":"10.1007/s11172-024-4303-x","DOIUrl":"10.1007/s11172-024-4303-x","url":null,"abstract":"<div><p>Spirocyclic scaffolds have received increasing interest because of their wide use in medicinal chemistry and the need for designing new effective drugs on their basis. Electroorganic synthesis is an environmentally friendly method for the preparation of organic compounds because hazardous and toxic redox reagents are replaced by electric current and the overall energy costs are reduced. Modern methods for the electrosynthesis of spiro compounds and the prospects of their development are analyzed. The review summarizes the data on the types of electrochemical and electrocatalytic methods. The potential practical applications of these methods for the preparation of individual classes of spirocycles are discussed.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 7","pages":"1845 - 1865"},"PeriodicalIF":1.7,"publicationDate":"2024-08-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142189263","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}
引用次数: 0
Selective C—H deuterium exchange in the oxacamphanyl moiety linked to the carbamide group 与碳酰胺基团相连的氧杂甘氨酰分子中的选择性 C-H 氘交换
IF 1.7 4区 化学
Russian Chemical Bulletin Pub Date : 2024-08-31 DOI: 10.1007/s11172-024-4312-9
A. I. Nichugovskiy, E. A. Eshtukova-Shcheglova, R. R. Fayzullin, D. V. Kuznetsov, V. V. Burmistrov, I. A. Novakov
{"title":"Selective C—H deuterium exchange in the oxacamphanyl moiety linked to the carbamide group","authors":"A. I. Nichugovskiy,&nbsp;E. A. Eshtukova-Shcheglova,&nbsp;R. R. Fayzullin,&nbsp;D. V. Kuznetsov,&nbsp;V. V. Burmistrov,&nbsp;I. A. Novakov","doi":"10.1007/s11172-024-4312-9","DOIUrl":"10.1007/s11172-024-4312-9","url":null,"abstract":"<div><p>In the <sup>1</sup>H NMR spectra (DMSO-d<sub>6</sub>) of 1,3-disubstituted ureas containing the 4,7,7-trimethyl-3-oxo-4-oxabicyclo[2.2.1]heptan-1-yl substituent, the signals for the CH<sub>2</sub>—CH<sub>2</sub> moiety appear as an ADMP-type spin system consisting of four doublets of doublets of doublets with chemical shifts in the range from 1.54 to 2.80 ppm. The experiment in CD<sub>3</sub>OD showed the disappearance of the signal at δ 2.80 and a change in the multiplicity of the other signals, which is indicative of the selective deuterium exchange of one of the four protons of the CH<sub>2</sub>—CH<sub>2</sub> group for a deuterium atom. This allows the selective modification of compounds containing the oxacamphanyl moiety.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 7","pages":"1936 - 1943"},"PeriodicalIF":1.7,"publicationDate":"2024-08-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142188989","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}
引用次数: 0
N-(2-Carboxyphenyl)oxalamides in the synthesis of the quinazoline central nervous system depressant methaqualone and fused biheterocyclic systems N-(2-羧基苯基)草酰胺在合成喹唑啉类中枢神经系统抑制剂甲喹酮和融合生物杂环系统中的应用
IF 1.7 4区 化学
Russian Chemical Bulletin Pub Date : 2024-08-31 DOI: 10.1007/s11172-024-4319-2
V. L. Mamedova, T. A. Kushatov, N. A. Tikhomirova, O. G. Sinyashin, V. A. Mamedov
{"title":"N-(2-Carboxyphenyl)oxalamides in the synthesis of the quinazoline central nervous system depressant methaqualone and fused biheterocyclic systems","authors":"V. L. Mamedova,&nbsp;T. A. Kushatov,&nbsp;N. A. Tikhomirova,&nbsp;O. G. Sinyashin,&nbsp;V. A. Mamedov","doi":"10.1007/s11172-024-4319-2","DOIUrl":"10.1007/s11172-024-4319-2","url":null,"abstract":"<div><p>A synthesis of the quinazolin-4-one pharmacological agent methaqualone from <i>N</i>-(2-carboxyphenyl)oxalamide was developed. A new method for the reductive cyclization of 3-(2-nitrophenyl)quinazolin-4-ones to benzimidazo[2,1-<i>b</i>]quinazolin-12(6<i>H</i>)-ones, the 6-deoxo-6-aza analogs of natural alkaloid tryptanthrine, was suggested and new derivatives of poorly available quinoxalinoquinazolinone fused system were synthesized.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 7","pages":"1996 - 2003"},"PeriodicalIF":1.7,"publicationDate":"2024-08-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142188996","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}
引用次数: 0
Unknown chemistry of acetylene: one-year achievements 未知的乙炔化学：一年来取得的成就
IF 1.7 4区 化学
Russian Chemical Bulletin Pub Date : 2024-08-31 DOI: 10.1007/s11172-024-4304-9
B. A. Trofimov, E. Yu. Schmidt
{"title":"Unknown chemistry of acetylene: one-year achievements","authors":"B. A. Trofimov,&nbsp;E. Yu. Schmidt","doi":"10.1007/s11172-024-4304-9","DOIUrl":"10.1007/s11172-024-4304-9","url":null,"abstract":"<div><p>The mini-review covers the results of the authors on acetylene chemistry achieved within 2022. This unusual format was selected in order to assess the dynamics and effectiveness of the developed approaches in result/time coordinates and the prospects for further research in these areas. The review discusses new reactions of acetylene and its derivatives that generally take place in superbasic media, in which the dual reactivity of the carbon—carbon triple bond (<i>i.e.</i> its ability to exhibit both nucleophilic and electrophilic properties) is most pronounced. The discovered by us reactions are the atom economical (they do not produce side products), energy- and resource-saving (they proceed at room or slightly elevated temperature), do not require transition metal catalysts, and can be implemented using inexpensive available starting compounds.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 7","pages":"1866 - 1883"},"PeriodicalIF":1.7,"publicationDate":"2024-08-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142189229","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}
引用次数: 0
Ti-catalyzed homocyclomagnesiation of (Z)-1,2,6-trienes in the stereoselective synthesis of 1Z,5Z,9Z,13Z-tetraenes 在立体选择性合成 1Z,5Z,9Z,13Z-四烯过程中钛催化 (Z)-1,2,6 三烯的同环镁化反应
IF 1.7 4区 化学
Russian Chemical Bulletin Pub Date : 2024-08-31 DOI: 10.1007/s11172-024-4309-4
E. Kh. Makarova, A. A. Makarov
{"title":"Ti-catalyzed homocyclomagnesiation of (Z)-1,2,6-trienes in the stereoselective synthesis of 1Z,5Z,9Z,13Z-tetraenes","authors":"E. Kh. Makarova,&nbsp;A. A. Makarov","doi":"10.1007/s11172-024-4309-4","DOIUrl":"10.1007/s11172-024-4309-4","url":null,"abstract":"<div><p>On the basis of the Ti-catalyzed homocyclomagnesiation of terminal 1,2-dienes, an effective method for the synthesis of 1<i>Z</i>,5<i>Z</i>,9<i>Z</i>,13<i>Z</i>-tetraenes in high yields and high stereoselectivity has been developed. A new approach to the synthesis of allenes with substituents containing <i>Z</i>-double bonds has been elaborated.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 7","pages":"1916 - 1922"},"PeriodicalIF":1.7,"publicationDate":"2024-08-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142188988","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}
引用次数: 0
Naphthoquinoid pigments of sea urchins. Trimethyl orthoacetate as an effective reagent for O-methylation of β-OH groups of spinazarin, spinochromes D and E, and echinochrome A 海胆的萘醌类色素。原乙酸三甲酯作为一种有效的试剂，用于对尖晶石色素、尖晶石色素 D 和 E 以及回声色素 A 的 β-OH 基团进行 O-甲基化反应
IF 1.7 4区 化学
Russian Chemical Bulletin Pub Date : 2024-08-31 DOI: 10.1007/s11172-024-4328-1
O. P. Shestak, N. N. Balaneva, V. L. Novikov, V. P. Glazunov
{"title":"Naphthoquinoid pigments of sea urchins. Trimethyl orthoacetate as an effective reagent for O-methylation of β-OH groups of spinazarin, spinochromes D and E, and echinochrome A","authors":"O. P. Shestak,&nbsp;N. N. Balaneva,&nbsp;V. L. Novikov,&nbsp;V. P. Glazunov","doi":"10.1007/s11172-024-4328-1","DOIUrl":"10.1007/s11172-024-4328-1","url":null,"abstract":"<div><p>Trimethyl orthoacetate (MeC(OMe)<sub>3</sub>, TMOA) is a convenient reagent for both selective and complete O-methylation of the β-OH groups of sea urchin pigments such as spinazarin, spinochromes D and E, and echinochrome A. The reactions of these compounds with TMOA make it possible to furnish preparative amounts of 6-monomethyl ethers of spinochrome D and echinochrome A, 7-monomethyl ether (namakochrome) and 6,7-dimethyl ether of spinochrome E, which are difficult to prepare by other methods, and to carry out complete O-methylation of all discussed pigments. Among the known O-methylating agents, TMOA is most suitable for the preparative syntheses of methyl ethers of polyhydroxynaphthazarins.</p></div>","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 7","pages":"2082 - 2098"},"PeriodicalIF":1.7,"publicationDate":"2024-08-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142189037","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}
引用次数: 0
III International Symposium “Non-covalent Interactions in Synthesis, Catalysis and Crystal Chemical Design” 第三届 "合成、催化和晶体化学设计中的非共价相互作用 "国际研讨会
IF 1.7 4区 化学
Russian Chemical Bulletin Pub Date : 2024-08-31 DOI: 10.1007/s11172-024-4333-4
{"title":"III International Symposium “Non-covalent Interactions in Synthesis, Catalysis and Crystal Chemical Design”","authors":"","doi":"10.1007/s11172-024-4333-4","DOIUrl":"10.1007/s11172-024-4333-4","url":null,"abstract":"","PeriodicalId":756,"journal":{"name":"Russian Chemical Bulletin","volume":"73 7","pages":"2121 - 2121"},"PeriodicalIF":1.7,"publicationDate":"2024-08-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142415123","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}
引用次数: 0
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