You-Qiang Guo, Long Liang, Zhen-Yu Wang, Xiang Wu, You-Gui Li
{"title":"TEMPO‐Mediated Cross‐Dehydrogenative Coupling for the Synthesis of Bis(indolyl)methanes","authors":"You-Qiang Guo, Long Liang, Zhen-Yu Wang, Xiang Wu, You-Gui Li","doi":"10.1002/ajoc.202400484","DOIUrl":"https://doi.org/10.1002/ajoc.202400484","url":null,"abstract":"A TEMPO‐oxidized method has been developed for the synthesis of bis(indolyl)‐methane derivatives by the cross‐dehydrogenative coupling between C(sp3)–H of para‐cresol derivatives and C(sp2)‐H of indoles in moderate yields under aqueous conditions. This approach has significant advantages in avoiding prefunctionalization, using water as the solvent and tolerating various functional groups.","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"17 1","pages":""},"PeriodicalIF":2.7,"publicationDate":"2024-11-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142665592","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":"Cover Feature: Diastereoselective Synthesis of Meso-1,2-Diarylethane-1,2-Diamines Via Sodium Reduction of Imidazolines (Asian J. Org. Chem. 11/2024)","authors":"Daniil R. Bazanov, Natalia A. Lozinskaya","doi":"10.1002/ajoc.202481102","DOIUrl":"https://doi.org/10.1002/ajoc.202481102","url":null,"abstract":"<p>The cover design illustrates a novel stereoselective approach to the synthesis of 1,2-diarylethane-1,2-diamines. The method proposed in this article utilizes widely available aromatic aldehydes and ammonia as starting substances. The stereoselectivity of the formation of cis-2,4,5-triarylimidazoline is due to Woodward–Hoffmann rules in the electrocyclic reactions. In article number e202400305 by Daniil R. Bazanov and Natalia A. Lozinskaya, the possibility of reduction of the amidine fragment of imidazoline with metallic sodium in tert-butyl alcohol was shown. This method allows to obtain alkyl- and alkoxyphenyl derivatives of meso-1,2-diarylethane-1,2-diamines in high yields. The ability to scale up the method to muttigram quantities is shown. A possible side reaction of the reduction to dibenzylamine derivatives is also shown on the cover design.\u0000 <figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 11","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-11-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202481102","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142665036","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}
Francisco A. A. Reis, Dr. Manda Sathish, Jorge Villaseñor, Dr. Fabiane M. Nachtigall, Dr. Leonardo S. Santos
{"title":"Front Cover: Pd-Monothiosquaramides: Efficient Catalysts for the Enantioselective Imine Reduction of Dihydro-β-Carbolines (Asian J. Org. Chem. 11/2024)","authors":"Francisco A. A. Reis, Dr. Manda Sathish, Jorge Villaseñor, Dr. Fabiane M. Nachtigall, Dr. Leonardo S. Santos","doi":"10.1002/ajoc.202481101","DOIUrl":"https://doi.org/10.1002/ajoc.202481101","url":null,"abstract":"<p>An efficient enantioselective synthesis of tetrahydro-β-carbolines using in situ generated chiral Pd-monothiosquaramides (Pd-MTSQs) was attempted. The Pd-MTSQs catalyzed imine reduction of dihydro-β-carbolines and produced chiral THBCs with excellent selectivity (up to 98% ee). Chiral alkyl-THBC isomers were observed with R configuration and S configuration perceived for chiral Aryl-THBCs. More details can be found in article number e202400245 by Nachtigall, Leonardo S. Santos, and co-workers.<figure>\u0000 <div><picture>\u0000 <source></source></picture><p></p>\u0000 </div>\u0000 </figure>\u0000 </p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 11","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-11-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202481101","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142665021","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}
Yun-Meng Li, Man Jiang, Jing Zhou, Prof. Dr. Hai-Lei Cui
{"title":"HBr/TMSO/HFIP Mediated Chemoselective Modifications of Pyrrolo[2,1-a]Isoquinolines","authors":"Yun-Meng Li, Man Jiang, Jing Zhou, Prof. Dr. Hai-Lei Cui","doi":"10.1002/ajoc.202400323","DOIUrl":"10.1002/ajoc.202400323","url":null,"abstract":"<p>The combination of HBr, TMSO (tetramethylene sulfoxide) and HFIP (hexafluoroisopropanol) has been utilized in the modification of pyrrolo[2,1-<i>a</i>]isoquinoline derivatives through bromination, dimerization and sulfenylation respectively. In these processes, HBr serves as the source of bromine and TMSO acts as an oxidant. HFIP also plays an essential role for the oxidative dimerization. Chemoselectivity can be easily controlled by adjusting the parameters such as reaction time, ratio of reagents and the addition of nucleophile.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 11","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-09-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142217014","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}
Dr. Elena Tretyakova, Dr. Liwen Hua, Anna Smirnova, Prof. Dr. Oxana Kazakova, Prof. Dr. Vladimir Zarubaev, Dr. Hongwei Jin, Dr. Huan Xu, Prof. Dr. Sulong Xiao
{"title":"Novel Abietane Type Sugar Triazole Hybrids and Amides against SARS-CoV-2 Spike Glycoprotein and Influenza A Virus","authors":"Dr. Elena Tretyakova, Dr. Liwen Hua, Anna Smirnova, Prof. Dr. Oxana Kazakova, Prof. Dr. Vladimir Zarubaev, Dr. Hongwei Jin, Dr. Huan Xu, Prof. Dr. Sulong Xiao","doi":"10.1002/ajoc.202400227","DOIUrl":"10.1002/ajoc.202400227","url":null,"abstract":"<p>Abietane type diterpenic (dehydroabietic, 2,3-dihydroquinopimaric and maleopimaric) acids were converted by the acid chloride method into a series of aliphatic and heterocyclic amine spacered conjugates. A number of structurally novel derivatives holding 1,2,3-triazole moieties were designed and synthesized by treating of the propargylated amides and esters with a sugar azides using the Cu(I)-catalyzed click chemistry approach. The synthesized <i>N</i>-containing diterpene derivatives were tested for their potential inhibition of influenza A/PuertoRico/8/34 (H1N1) virus in MDCK cell culture and SARS-CoV-2 pseudovirus in BHK-21-hACE2 cells. Among tested forty-five compounds ten derivatives were the most efficacious against influenza virus A with IC<sub>50</sub> 0.7–63.4 μM together with high selectivity index SI value from 11 from 94. Dihydroquinopimaric acid <i>N</i>-ethylpiperazine-amide and dehydroabietic acid 1,2,3-triazoles spacered with glucose and lactose showed anti-SARS-CoV-2 pseudovirus activity with EC<sub>50</sub> values of 1.79–25.46 μM. Molecular docking and dynamics modeling investigated the binding mode of the lead compounds into the binding pocket of influenza A virus M2 protein and the RBD domain of SARS-CoV-2 spike glycoprotein.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 11","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-09-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142227007","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":"Facile and Metal-Free Synthesis of Isoflavones Using α-Aryl-β,β-Ditosyloxy Ketones","authors":"Omkar Bains, Ashish Kumar, Raj Kamal, Ravinder Kumar, Rajesh Kumar, Tanmay Rom, Avijit Kumar Paul","doi":"10.1002/ajoc.202400336","DOIUrl":"10.1002/ajoc.202400336","url":null,"abstract":"<p>Considering the drawbacks associated with available synthetic methodologies of isoflavones, herein we have reported a metal-free and eco-friendly approach to these natural products. In the present study, we have carried out the synthesis of eight isoflavone derivatives <b>7a</b>–<b>7h</b> using α-aryl-β,β-ditosyloxy ketone protocol. Initially, we have protected the 2’-hydroxy group of respective chalcone moiety in order to remove its interference under reaction conditions. The protected chalcones were then subjected to 1,2-aryl migration by being treated with hydroxy(tosyloxy)iodobenzene (HTIB) reagent in a non-nucleophilic solvent (CH<sub>2</sub>Cl<sub>2</sub>). This migration furnished the formation of α-aryl-β,β-ditosyloxy ketones via C−C bond formation from their corresponding chalcones in moderate to good yields (55–82 %). The ambiguity regarding the exact molecular structure of the α-aryl-β,β-ditosyloxy ketones was examined through the single crystal X-ray diffraction data. At last, the synthesis of isoflavones was carried out in moderate to good yields (50–80 %) by performing the reaction of α-aryl-β,β-ditosyloxy ketones with sodium hydroxide in aqueous methanol.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 11","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-08-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142217017","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}
Dr. Sari Deketelaere, Dr. Carlos Díez-Poza, Margot Aelbrecht, Jonas Mortier, Bram Van Den Bossche, Dr. Jorick Franceus, Prof. Dr. Tom Desmet, Prof. Dr. Kristof Van Hecke, Prof. Dr. Christian V. Stevens, Prof. Dr. Matthias D'hooghe
{"title":"Synthesis of Pyrrolidine-fused β-lactams as Potential β-lactamase Inhibitors","authors":"Dr. Sari Deketelaere, Dr. Carlos Díez-Poza, Margot Aelbrecht, Jonas Mortier, Bram Van Den Bossche, Dr. Jorick Franceus, Prof. Dr. Tom Desmet, Prof. Dr. Kristof Van Hecke, Prof. Dr. Christian V. Stevens, Prof. Dr. Matthias D'hooghe","doi":"10.1002/ajoc.202400364","DOIUrl":"10.1002/ajoc.202400364","url":null,"abstract":"<p>A synthetic protocol for the preparation of novel 3,4-pyrrolidine-fused β-lactams was developed. The proposed 2,6-diazabicyclo[3.2.0]heptan-7-one scaffolds were constructed through an amido group-induced, potassium <i>tert</i>-butoxide-promoted intramolecular ring closure of 3-acylamino-4-oxiranyl-β-lactams as the key reaction step. Alternatively, the desired cyclization was also effected by means of a scandium triflate-mediated catalytic approach. In this way, a set of stereodefined 3,4-pyrrolidine-fused β-lactams was synthesized, which were preliminary evaluated as β-lactamase inhibitors. These first-line biological assessments led to the identification of a 2-benzoyl-6-(4-methoxyphenyl)-substituted diazabicyclo structure as an eligible starting point for further β-lactamase inhibitor optimization studies.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 11","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-08-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142217018","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}
Qian-Qian Wu, Yan Wang, Muliang Zhang, Shi-Kai Tian
{"title":"Direct Substitution of 2-Aminotropones with Potassium Allyltrifluoroborates through Transition-Metal-Free C−N Bond Cleavage","authors":"Qian-Qian Wu, Yan Wang, Muliang Zhang, Shi-Kai Tian","doi":"10.1002/ajoc.202400386","DOIUrl":"10.1002/ajoc.202400386","url":null,"abstract":"<p>The poor nucleofugality of the amino group renders the C−N bond functionalization of primary aromatic amines highly challenging. Herein, we report a direct substitution reaction of 2-aminotropones, bearing a unique non-benzenoid seven-membered aromatic ring that exists in some natural products and bioactive molecules, with potassium allyltrifluoroborates through C−N bond cleavage under transition-metal-free conditions. The amino group of 2-aminotropones were directly substituted with potassium allyltrifluoroborates in the presence of sodium bicarbonate, delivering structurally diverse 2-allyltropones in moderate to good yields. The reaction is free of directing groups, activating groups and transition metals, providing a convenient method to access substituted tropones.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 11","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-08-27","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142217019","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}
Tianyang Zhang, Xianfu Fang, Xin Wang, Huicong Wang, Gong Zhang, Wei Fang, Yangfeng Li, Yizhou Li
{"title":"DNA-Compatible Nitriles Hydrolysis for Late-Stage Functionalization of DNA-Encoded Libraries","authors":"Tianyang Zhang, Xianfu Fang, Xin Wang, Huicong Wang, Gong Zhang, Wei Fang, Yangfeng Li, Yizhou Li","doi":"10.1002/ajoc.202400280","DOIUrl":"10.1002/ajoc.202400280","url":null,"abstract":"<p>Primary amides play a crucial role in organic and pharmaceutical synthesis. Herein, we present a rapid and convenient method for transforming diverse DNA-conjugated nitriles into primary amides utilizing hydrogen peroxide and potassium carbonate. The substrate scope and DEL compatibility of this reaction were thoroughly investigated, revealing a wide range of substrates with moderate-to-excellent conversion. This on-DNA transformation holds significant promise for constructing DNA-encoded libraries (DELs) and enabling late-stage functionalization to expand chemical diversity. Our approach not only highlights the versatility of the method but also underscores its potential for broad applications in organic and pharmaceutical synthesis.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 11","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-08-25","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142217020","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":"Non-Electronic Activation of Anthracenes Using Steric Repulsion of the 9-Substituent with Chloro Groups at the peri-Positions","authors":"Annisa Indah Reza, Kento Iwai, Nagatoshi Nishiwaki","doi":"10.1002/ajoc.202400381","DOIUrl":"10.1002/ajoc.202400381","url":null,"abstract":"<p>We investigated how the introduction of substituent at the 9- or 10-position of the 1,8-dichloroanthracene framework affects the horizontal and vertical distortions of the anthracene rings. The 9-substituted anthracenes showed higher distortions than their 10-substituted counterparts due to the steric repulsion with two chloro groups at the <i>peri</i>-positions. The distortion of anthracene framework affected their reactivity. Indeed, 9-substituted anthracenes exhibited higher reactivity to undergo the Diels–Alder reaction with maleic anhydride, which was a result of non-electronic activation.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 11","pages":""},"PeriodicalIF":2.8,"publicationDate":"2024-08-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142217022","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}