{"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}
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}
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}
{"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}
{"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}
{"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}
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}
{"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}
Pavlo V. Zadorozhnii, Ihor O. Pokotylo, V. Kiselev, A. V. Kharchenko, Oxana V. Okhtina
{"title":"Synthesis and spectral characteristics of N-(1-([1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-ylamino)-2,2,2-trichloroethyl)carboxamides","authors":"Pavlo V. Zadorozhnii, Ihor O. Pokotylo, V. Kiselev, A. V. Kharchenko, Oxana V. Okhtina","doi":"10.1515/hc-2019-0020","DOIUrl":"https://doi.org/10.1515/hc-2019-0020","url":null,"abstract":"Abstract Based on readily available N-(2,2,2-trichloro-1-hydroxyethyl)carboxamides, N-(2,2,2-trichloro-1-(3-(3-mercapto-4H-1,2,4-triazol-4-yl)thioureido)ethyl) carboxamides, dehydrosulfurization–under the influence of excess HgO–led to the formation of N-(1-([1,2,4] triazolo[3,4-b][1,3,4]thiadiazol-6-ylamino)-2,2,2-trichloroethyl)carboxamides. The reaction was carried out in boiling glacial acetic acid for 1-1.5 hours. The cyclization products were obtained in 42-62% yields and easily isolated from the reaction mixture. The structure of all synthesized compounds was confirmed by complex spectral studies.","PeriodicalId":12914,"journal":{"name":"Heterocyclic Communications","volume":"25 1","pages":"130 - 137"},"PeriodicalIF":2.3,"publicationDate":"2019-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://sci-hub-pdf.com/10.1515/hc-2019-0020","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"48452903","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}