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Asymmetric Mannich Reaction: Synthesis of Novel Chiral 5-(substituted aryl)-1,3,4-Thiadiazole Derivatives with Anti-Plant-Virus Potency 不对称曼尼希反应:具有抗植物病毒活性的新型手性5-(取代芳基)-1,3,4-噻二唑衍生物的合成
IF 2.3 3区 化学
Heterocyclic Communications Pub Date : 2019-04-03 DOI: 10.1515/HC-2019-0005
Bai Song, Yunying Zhu, Wu Qin
{"title":"Asymmetric Mannich Reaction: Synthesis of Novel Chiral 5-(substituted aryl)-1,3,4-Thiadiazole Derivatives with Anti-Plant-Virus Potency","authors":"Bai Song, Yunying Zhu, Wu Qin","doi":"10.1515/HC-2019-0005","DOIUrl":"https://doi.org/10.1515/HC-2019-0005","url":null,"abstract":"","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"25 1","pages":"47-51"},"PeriodicalIF":2.3,"publicationDate":"2019-04-03","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1515/HC-2019-0005","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"66834206","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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: 3
Synthesis and fungicidal activity of novel imidazo[4, 5-b]pyridine derivatives 新型咪唑并[4,5-b]吡啶衍生物的合成及其杀菌活性
IF 2.3 3区 化学
Heterocyclic Communications Pub Date : 2019-01-01 DOI: 10.1515/hc-2019-0003
Daoxin Wu, Minhua Liu, Zhong Li, Mingming Dang, Xingping Liu, Jianming Li, Lu Huang, Yeguo Ren, Zai Zhang, Weidong Liu, Aiping Liu
{"title":"Synthesis and fungicidal activity of novel imidazo[4, 5-b]pyridine derivatives","authors":"Daoxin Wu, Minhua Liu, Zhong Li, Mingming Dang, Xingping Liu, Jianming Li, Lu Huang, Yeguo Ren, Zai Zhang, Weidong Liu, Aiping Liu","doi":"10.1515/hc-2019-0003","DOIUrl":"https://doi.org/10.1515/hc-2019-0003","url":null,"abstract":"Abstract A series of novel imidazo[4,5-b]pyridine derivatives were synthesized and their structures were characterized by NMR spectroscopy, mass spectrometry and elemental analysis. The results of bioassays showed that some compounds exhibit good fungicidal activity against Puccinia polysora In particular, compound 7b showed an EC50 value of 4.00 mg/L, which was comparable with that of tebuconazole. Besides, preliminary structure-activity relationship was discussed.","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"25 1","pages":"14 - 8"},"PeriodicalIF":2.3,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1515/hc-2019-0003","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48935698","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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: 6
Asymmetric total synthesis of filamentous fungi related resorcylic acid lactones 7-epi-zeaenol and zeaenol 丝状真菌相关间苯二酚内酯7-表玉米烯醇和玉米烯醇的不对称全合成
IF 2.3 3区 化学
Heterocyclic Communications Pub Date : 2019-01-01 DOI: 10.1515/hc-2019-0015
Sai Reddy Doda, Avula Raghavendar, S. Haridasyam, Chandra Shekar Putta, B. K. Rao, Sudhakar Kadari
{"title":"Asymmetric total synthesis of filamentous fungi related resorcylic acid lactones 7-epi-zeaenol and zeaenol","authors":"Sai Reddy Doda, Avula Raghavendar, S. Haridasyam, Chandra Shekar Putta, B. K. Rao, Sudhakar Kadari","doi":"10.1515/hc-2019-0015","DOIUrl":"https://doi.org/10.1515/hc-2019-0015","url":null,"abstract":"Abstract An efficient, short and, a convenient asymmetric total synthesis of filamentous fungi related resorcylic acid lactones 7-epi-zeaenol (2) and zeaenol (1) have been achieved in 7 and 9 linear steps with the high overall yield of 32% and 21% respectively, from the known intermediate 13. Mitsunobu inversion, De Brabander’s protocol for macrolactonisation, Heck cross-coupling, diastereoselective alkyne aldehyde coupling and Ohira–Bestmann alkynylation are the key reactions.","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"25 1","pages":"78 - 84"},"PeriodicalIF":2.3,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1515/hc-2019-0015","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43681974","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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: 4
Magnesium porphyrazine with peripheral methyl (3,5-dibromophenylmethyl)amino groups – synthesis and optical properties 具有外围甲基（3,5-二溴苯基甲基）氨基的卟啉镁的合成和光学性能
IF 2.3 3区 化学
Heterocyclic Communications Pub Date : 2019-01-01 DOI: 10.1515/hc-2019-0001
E. Wieczorek, Jaroslaw Piskorz, L. Popenda, S. Jurga, J. Mielcarek, T. Gośliński
{"title":"Magnesium porphyrazine with peripheral methyl (3,5-dibromophenylmethyl)amino groups – synthesis and optical properties","authors":"E. Wieczorek, Jaroslaw Piskorz, L. Popenda, S. Jurga, J. Mielcarek, T. Gośliński","doi":"10.1515/hc-2019-0001","DOIUrl":"https://doi.org/10.1515/hc-2019-0001","url":null,"abstract":"Abstract Novel magnesium(II) porphyrazine with peripheral methyl(3,5-dibromophenylmethyl)amine groups was synthesized in a multi-step procedure starting from commercially available diaminomaleonitrile. All intermediates and the final macrocycle were characterized using UV–Vis, FT-IR, MS and various NMR techniques. The absorption and emission properties of the macrocycle were evaluated in N,N-dimethylformamide, dimethyl sulfoxide, and dichloromethane. The potential photosensitizing activity was evaluated by assessing the ability of the macrocycle to generate singlet oxygen in dimethyl sulfoxide and N,N-dimethylformamide.","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"25 1","pages":"1 - 7"},"PeriodicalIF":2.3,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1515/hc-2019-0001","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41816393","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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: 4
Synthesis of polycyclic phosphonates via an intramolecular Diels-Alder reaction of 2-benzoylbenzalaldehyde and alkenyl phosphites 2-苯甲酰基苯甲醛与亚磷酸烯基酯的分子内Diels-Alder反应合成多环膦酸酯
IF 2.3 3区 化学
Heterocyclic Communications Pub Date : 2019-01-01 DOI: 10.1515/hc-2019-0011
K. Yamana, H. Nakano
{"title":"Synthesis of polycyclic phosphonates via an intramolecular Diels-Alder reaction of 2-benzoylbenzalaldehyde and alkenyl phosphites","authors":"K. Yamana, H. Nakano","doi":"10.1515/hc-2019-0011","DOIUrl":"https://doi.org/10.1515/hc-2019-0011","url":null,"abstract":"Abstract In this paper, we present a Lewis-acid-promoted reaction of 2-benzoylbenzaldehyde and trialkenyl phosphites, which resulted in the formation of polycyclic phosphonates. The reaction proceeded via nucleophilic attack of trialkenyl phosphite on the carbonyl carbon of 2-benzoylbenzaldehyde. The subsequent intramolecular Diels-Alder reaction led to the formation of the cyclic phosphonate.","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"25 1","pages":"73 - 77"},"PeriodicalIF":2.3,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1515/hc-2019-0011","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"43199746","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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: 2
Facile One-pot Protocol of Derivatization Nitropyridines: Access to 3-Acetamidopyridin-2-yl 4-methylbenzenesulfonate Derivatives 简单的一锅衍生化硝基吡啶方案:获得3-乙酰氨基吡啶-2-基4-甲基苯磺酸衍生物
IF 2.3 3区 化学
Heterocyclic Communications Pub Date : 2019-01-01 DOI: 10.1515/hc-2019-0017
Ling‐Zhi Lin, Xiaoguang Chen, Junhao Zhao, Suitao Lin, Guojian Ma, Xiaojian Liao, Pengju Feng
{"title":"Facile One-pot Protocol of Derivatization Nitropyridines: Access to 3-Acetamidopyridin-2-yl 4-methylbenzenesulfonate Derivatives","authors":"Ling‐Zhi Lin, Xiaoguang Chen, Junhao Zhao, Suitao Lin, Guojian Ma, Xiaojian Liao, Pengju Feng","doi":"10.1515/hc-2019-0017","DOIUrl":"https://doi.org/10.1515/hc-2019-0017","url":null,"abstract":"Abstract This paper discloses an efficient one-pot protocol to convert easily accessible 3-nitropyridines to 3-acetamidopyridin-2-yl 4-methylbenzenesulfonate derivatives which are core structures of many pharmaceutical molecules. The strategy successfully combined a three-step reaction in one pot via progressively adding different reactants at rt. The reaction displays good functional group tolerance and regioselectivity. Structurally diversified 3-nitropyridine could be time-efficiently (3.5 h) derivatized to various functional 2-O,3-N-pyridines which are apt for further elaborations. The transformation was amenable to gram-scale synthesis.","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"25 1","pages":"138 - 145"},"PeriodicalIF":2.3,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1515/hc-2019-0017","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"41576276","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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: 1
Remarkable electronic effect on the total stereoselectivity of the cycloaddition reaction of arylnitrile oxides with pyrrol-2-one derivatives 对芳腈氧化物与吡咯-2- 1衍生物环加成反应的总立体选择性有显著的电子效应
IF 2.3 3区 化学
Heterocyclic Communications Pub Date : 2019-01-01 DOI: 10.1515/hc-2019-0014
A. Guesmi, N. B. Hamadi
{"title":"Remarkable electronic effect on the total stereoselectivity of the cycloaddition reaction of arylnitrile oxides with pyrrol-2-one derivatives","authors":"A. Guesmi, N. B. Hamadi","doi":"10.1515/hc-2019-0014","DOIUrl":"https://doi.org/10.1515/hc-2019-0014","url":null,"abstract":"Abstract The regiospecific 1,3-dipolar cycloaddition of 1,5-dihydropyrrol-2-one and arylnitrile oxides derivatives have been investigated. The asymmetric induction expected by the chiral centre of the 5-hydroxy-3-methyl-1,5-dihydropyrrol-2-one derivatives was very effective, single diastereoisomers anti-3 was formed. The diastereoselectivity was linked to the destabilization of the syn transition state as a result of the electrostatic repulsion between the hydroxy group of the dihydropyrrol-2-one derivatives and the atom oxygen of the dipole.","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"25 1","pages":"60 - 65"},"PeriodicalIF":2.3,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1515/hc-2019-0014","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"46050780","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Substrate-controlled Diastereoselective Michael Addition of Alkylidene Malonates by Grignard Reagents 格氏试剂对亚烷基丙二酸酯底物控制的双立体选择性迈克尔加成反应
IF 2.3 3区 化学
Heterocyclic Communications Pub Date : 2019-01-01 DOI: 10.1515/hc-2019-0019
Wei Zhou, Q. Xiao, Yuanyuan Chang, Qifa Liu, Xiaohao Zang, Mengmeng Hu, Xiaofei Zeng, Z. Du, Guifa Zhong
{"title":"Substrate-controlled Diastereoselective Michael Addition of Alkylidene Malonates by Grignard Reagents","authors":"Wei Zhou, Q. Xiao, Yuanyuan Chang, Qifa Liu, Xiaohao Zang, Mengmeng Hu, Xiaofei Zeng, Z. Du, Guifa Zhong","doi":"10.1515/hc-2019-0019","DOIUrl":"https://doi.org/10.1515/hc-2019-0019","url":null,"abstract":"Abstract Herein is described a diastereoselective Michael addition of Grignard reagents to α, β- unsaturated diethyl malonates incorporated with a 2-oxazolidone chiral auxiliary. The catalyst-free Michael addition proceeds with good chemical efficiency and excellent stereoselectivity; and it provides new thoughts to the asymmetric synthesis of β-substituted β3 amino acid derivatives.","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"25 1","pages":"116 - 121"},"PeriodicalIF":2.3,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1515/hc-2019-0019","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"44623078","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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
Zinc Chloride Catalyzed Amino Claisen Rearrangement of 1-N-Allylindolines: An Expedient Protocol for the Synthesis of Functionalized 7-Allylindolines 氯化锌催化1-N-烯丙基吲哚的氨基克莱森重排反应：合成官能化7-烯丙基吲哚
IF 2.3 3区 化学
Heterocyclic Communications Pub Date : 2019-01-01 DOI: 10.1515/hc-2019-0010
S. Jain
{"title":"Zinc Chloride Catalyzed Amino Claisen Rearrangement of 1-N-Allylindolines: An Expedient Protocol for the Synthesis of Functionalized 7-Allylindolines","authors":"S. Jain","doi":"10.1515/hc-2019-0010","DOIUrl":"https://doi.org/10.1515/hc-2019-0010","url":null,"abstract":"Abstract 7-Allylindolines are valuable synthons for designing biologically active molecular libraries. Lewis acid catalyzed amino-Claisen rearrangement provides a one pot synthetic entry to these heteroarenes. In this context, Zinc chloride (ZnCl2)–N,N-dimethylformamide system efficiently catalyzed amino-Claisen rearrangements of 1-N-allylindolines to 7-allylindolines. The rearrangement is influenced by stereoelectronic effects of substituents present in 1-N-allylindolines. The substrates containing electron donating functionalities underwent rearrangement at lower temperature than substrates with electron withdrawing functional groups. The regioselectivity of the process is governed by the substitution pattern on allyl moiety in 1-N-allylindoline as well as ZnCl2 catalyst loading in the reaction system.","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"25 1","pages":"22 - 26"},"PeriodicalIF":2.3,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1515/hc-2019-0010","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"49643284","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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: 3
Combined XRD-paramagnetic 13C NMR spectroscopy of 1,2,3-triazoles for revealing copper traces in a Huisgen click-chemistry cycloaddition. A model case 1,2,3-三唑的组合XRD顺磁13C NMR光谱用于揭示Huisgen点击化学环加成中的铜痕量。一个典型案例
IF 2.3 3区 化学
Heterocyclic Communications Pub Date : 2019-01-01 DOI: 10.1515/hc-2019-0018
Daniel Canseco-González, J. O., J. Herbert-Pucheta
{"title":"Combined XRD-paramagnetic 13C NMR spectroscopy of 1,2,3-triazoles for revealing copper traces in a Huisgen click-chemistry cycloaddition. A model case","authors":"Daniel Canseco-González, J. O., J. Herbert-Pucheta","doi":"10.1515/hc-2019-0018","DOIUrl":"https://doi.org/10.1515/hc-2019-0018","url":null,"abstract":"Abstract Copper-catalyzed Alkyne-Azide Cycloaddition (CuAAC) click chemistry robustness has been demonstrated over recent years to produce 1,2,3-triazoles with excellent yields at mild conditions with simple purification methods. However, the consequences of having copper paramagnetic traces in final products, which complicate spectroscopic assignments and can produce inaccurate conclusions, has been scarcely discussed. Herein we present a strategy that combines X-Ray Diffraction (XRD) with 13C- paramagnetic Nuclear Magnetic Resonance spectroscopy, in order to demonstrate the presence of paramagnetic metal traces at standard Huisgen synthesis and purification conditions. We also demonstrate that the derivatization of 1,4-disubstituted-1,2,3-triazoles to produce 1,3,4,-trisubstituted-1,2,3.triazolium salts, promotes an efficient removal of Cu(II/I) moieties. Evidence of paramagnetic metal moieties is given using XRD structural analysis of abnormalities in torsional angles between substituents and the 1,2,3-triazole center, in parallel to 13C- paramagnetic NMR chemical shift and line width analysis. As model systems to demonstrate the importance of characterizing paramagnetic traces, we present the synthesis of novel 1-((3s,5s,7s)-adamantan-1-yl)-4-cyclopropyl-1H-1,2,3-triazole and its derivatized 1-((3s,5s,7s)-adamantan-1-yl)-4-cyclopropyl-3-methyl-1H-[1,2,3]-triazol-3-ium triflate salt.","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"25 1","pages":"106 - 98"},"PeriodicalIF":2.3,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1515/hc-2019-0018","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"42224262","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":3,"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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