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Modular synthesis of unsymmetrical indolyl diketones from ynediones via sequential aza-Michael addition/C–H functionalization 通过氮杂迈克尔加成/C-H 官能化顺序，从乙烯酮模块化合成不对称吲哚基二酮
IF 3.2 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-06 DOI: 10.1039/d4ob00946k
Abdul Naveed, Debojyoti Bag, Sanghapal D. Sawant
{"title":"Modular synthesis of unsymmetrical indolyl diketones from ynediones via sequential aza-Michael addition/C–H functionalization","authors":"Abdul Naveed, Debojyoti Bag, Sanghapal D. Sawant","doi":"10.1039/d4ob00946k","DOIUrl":"https://doi.org/10.1039/d4ob00946k","url":null,"abstract":"Herein, we disclose an efficient approach for the synthesis of unsymmetrical indolyl diketones from easily accessible 1,2-alkynediones involving a sequential aza-Michael addition/C–H Functionalization process. The two-step, one-pot strategy involves the aza-Michael addition of an aniline generating the <em>N</em>-aryl enaminones followed by iodine-mediated C–H functionalization.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-09-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142249943","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
Samarium diiodide/samarium-mediated direct deoxygenative hydroborylation of ketones with hydroborane esters 二碘化钐/钐介导的酮与氢硼烷酯的直接脱氧氢硼化反应
IF 3.2 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-06 DOI: 10.1039/d4ob01287a
Yongqi Liang, Yilin Ma, Wei Zhou, Yongmei Cui, Michal Szostak, Chengwei Liu
{"title":"Samarium diiodide/samarium-mediated direct deoxygenative hydroborylation of ketones with hydroborane esters","authors":"Yongqi Liang, Yilin Ma, Wei Zhou, Yongmei Cui, Michal Szostak, Chengwei Liu","doi":"10.1039/d4ob01287a","DOIUrl":"https://doi.org/10.1039/d4ob01287a","url":null,"abstract":"A direct deoxygenative hydroborylation of ketones with hydroborane ester promoted by a combination of samarium diiodide, samarium and nickel has been developed. In this method, secondary alkyl borate esters are synthesized from unactivated ketones with hydroborane esters in one step. A broad substrate scope and excellent selectivity toward C<img alt=\"[double bond, length as m-dash]\" border=\"0\" src=\"https://www.rsc.org/images/entities/char_e001.gif\">O cleavage has been demonstrated. This approach represents a general method for the construction of versatile secondary alkyl borate esters from unactivated ketones.</img>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-09-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142202348","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
One-pot sequential synthesis of unsymmetrical diarylmethanes using methylene chloride as a C1-synthon 以二氯甲烷为 C1-质子，单锅顺序合成不对称的二芳基甲烷
IF 3.2 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-06 DOI: 10.1039/d4ob01158a
Xueli Cui, Chunming Chen, Mei Xie, Taotao Zhao, Jianfeng Yi, Weiqiang Sun, Zhuang Xiong, Jinhui Hu, Wing-Leung Wong, Jia-Qiang Wu
{"title":"One-pot sequential synthesis of unsymmetrical diarylmethanes using methylene chloride as a C1-synthon","authors":"Xueli Cui, Chunming Chen, Mei Xie, Taotao Zhao, Jianfeng Yi, Weiqiang Sun, Zhuang Xiong, Jinhui Hu, Wing-Leung Wong, Jia-Qiang Wu","doi":"10.1039/d4ob01158a","DOIUrl":"https://doi.org/10.1039/d4ob01158a","url":null,"abstract":"Bisindolylmethane (BIM) and its derivatives are widely used in the pharmaceutical industry due to their significant biological activities. However, most reported synthetic methods are focused on the synthesis of symmetric BIMs, while the synthesis of unsymmetrical BIMs remains a challenge. Herein, an unprecedented two-step one-pot method to afford unsymmetrically substituted 3,3′-BIM frameworks, using methylene chloride (DCM) as the C1-synthon is reported. In this protocol, the formation of two C–C bonds can be achieved <em>via</em> a one-pot reaction. The utility of commercially available phenols and anilines was also demonstrated in the construction of unsymmetrical diarylmethanes. This protocol provides a straightforward approach to access diverse unsymmetrical diarylmethane derivatives under simple and mild conditions. The broad substrate compatibility and good functional group tolerance of the protocol support its practical application potential.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-09-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142202350","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-dependent regiodivergence in [3 + 2] annulation reactions of 2-(phenacylethylidene)cyclobutanones with thioureas 2-(苯基亚乙基)环丁酮与硫脲的[3 + 2]环化反应中的底物依赖性变构
IF 3.2 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-06 DOI: 10.1039/d4ob01103a
Stefano Barranco, Alessio Pagnanini, Federico Cuccu, Pierluigi Caboni, Régis Guillot, David J. Aitken, Angelo Frongia
{"title":"Substrate-dependent regiodivergence in [3 + 2] annulation reactions of 2-(phenacylethylidene)cyclobutanones with thioureas","authors":"Stefano Barranco, Alessio Pagnanini, Federico Cuccu, Pierluigi Caboni, Régis Guillot, David J. Aitken, Angelo Frongia","doi":"10.1039/d4ob01103a","DOIUrl":"https://doi.org/10.1039/d4ob01103a","url":null,"abstract":"The [3 + 2] annulation reaction between a thiourea, an ambident dinucleophile, and a 2-(phenacylethylidene)cyclobutanone, containing a novel pull–pull alkene system, could in principle proceed with several chemo- and regioselectivity profiles. Here we describe a convenient synthesis of the functionalized cyclobutanone substrates and show that they react with thioureas in a manner that is rationalized mechanistically in terms of the steric and electronic effects at play. The [3 + 2] annulation proceeds in mild, additive-free conditions to provide access to previously unknown cyclobutane-fused imidazolidine-2-thione and thiazolidine-2-imine derivatives in good yields.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-09-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142202347","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
A direct oxidative esterification of aldehydes with alcohols mediated by photochemical C-H bromination. 以光化学 C-H 溴化反应为介导的醛与醇的直接氧化酯化反应。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-06 DOI: 10.1039/d4ob01237b
Haru Ando, Sakura Kodaki, Hiroyoshi Takamura, Isao Kadota, Kenta Tanaka
{"title":"A direct oxidative esterification of aldehydes with alcohols mediated by photochemical C-H bromination.","authors":"Haru Ando, Sakura Kodaki, Hiroyoshi Takamura, Isao Kadota, Kenta Tanaka","doi":"10.1039/d4ob01237b","DOIUrl":"https://doi.org/10.1039/d4ob01237b","url":null,"abstract":"<p><p>The photochemical direct esterification of aldehydes with alcohols <i>via in situ</i>-generated acyl-bromides presented in this report is an attractive complementary addition to hitherto reported methods, as these are usually carried out in a two-step, one-pot procedure in order to avoid side reactions such as the oxidation of alcohols by halogen sources.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-09-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142138676","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
Base-mediated synthesis of aryl enol ethers from α-aryl allylic alcohols and arylsulfonium salts. 以α-芳基烯丙基醇和芳基锍盐为原料，通过碱介导合成芳基烯醇醚。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-05 DOI: 10.1039/d4ob01220h
Yu-Fei Yao, Jia-Wei Song, Cheng-Pan Zhang
{"title":"Base-mediated synthesis of aryl enol ethers from α-aryl allylic alcohols and arylsulfonium salts.","authors":"Yu-Fei Yao, Jia-Wei Song, Cheng-Pan Zhang","doi":"10.1039/d4ob01220h","DOIUrl":"https://doi.org/10.1039/d4ob01220h","url":null,"abstract":"<p><p>A concise synthesis of aryl enol ethers from allylic alcohols and arylsulfonium salts by simply using an inorganic base as a mediator is described. The reaction enabled the facile conversion of various α-aryl allylic alcohols into the corresponding aryl enol ethers in good yields with excellent selectivity. The results demonstrated that both symmetric triarylsulfonium triflate and 10-methyl-5-aryl-5,10-dihydrophenothiazin-5-ium salts were effective arylation reagents for the base-initiated selective <i>O</i>-arylation and isomerization of α-aryl allylic alcohols. This reaction represents the first use of arylsulfonium salts as arylation reagents to access aryl enol ethers directly from allylic alcohols.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142131246","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
Mechanochemical deprotection of t-butoxycarbonyl (Boc) group using basic alumina 使用碱性氧化铝对叔丁氧羰基 (Boc) 进行机械化学脱保护处理
IF 3.2 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-05 DOI: 10.1039/d4ob01091d
Kaidi Tian, Tingna Cai, Zedong Zhu, Kai Cheng, Lemao Yu, Yong Li
{"title":"Mechanochemical deprotection of t-butoxycarbonyl (Boc) group using basic alumina","authors":"Kaidi Tian, Tingna Cai, Zedong Zhu, Kai Cheng, Lemao Yu, Yong Li","doi":"10.1039/d4ob01091d","DOIUrl":"https://doi.org/10.1039/d4ob01091d","url":null,"abstract":"A solvent-free, operationally simple, and chemoselective mechanochemical method for <em>t</em>-butoxycarbonyl (Boc) deprotection is described. In a planetary ball mill, <em>N</em>-Boc groups from protected heterocycles, amides, and anilines, as well as <em>O</em>-Boc groups from carbonates, can be removed selectively, using basic alumina. This high-yielding protocol avoids tedious extraction and column chromatography.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142202352","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
Lewis base promoted [4 + 2] annulation of o-acylamino-aryl MBH carbonates with isatin 路易斯碱促进邻氨基芳基甲基溴碳酸盐与异靛红的[4 + 2]环化反应
IF 3.2 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-05 DOI: 10.1039/d4ob01240b
Li-Wen Shen, Nian Luo, Yun-Qing Jia, Guang-Wei Wang, Shu-Pei Yuan, Min Xiang
{"title":"Lewis base promoted [4 + 2] annulation of o-acylamino-aryl MBH carbonates with isatin","authors":"Li-Wen Shen, Nian Luo, Yun-Qing Jia, Guang-Wei Wang, Shu-Pei Yuan, Min Xiang","doi":"10.1039/d4ob01240b","DOIUrl":"https://doi.org/10.1039/d4ob01240b","url":null,"abstract":"The first example of Lewis base promoted [4 + 2] annulation between <em>o</em>-acylamino-aryl MBH carbonates and isatin has been developed. This methodology exhibits excellent substrate applicability and has synthesized 1,4-dihydrospiro benzo[<em>d</em>][1,3]oxazine-oxindoles with yields up to 98%. The practical value of this method is underscored by its successful application in a 50-fold scale-up.","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":3.2,"publicationDate":"2024-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142202351","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
p-TSA catalyzed 6-endo-trig/dig cyclization of 5-aminopyrazoles and 3°/2°-propargylic alcohols: access to pyrazolo[1,5-a]dihydropyrimidines and pyrazolo[3,4-b]pyridines. p-TSA 催化 5-氨基吡唑和 3°/2°-丙炔醇的 6-endo-trig/dig 环化反应：获得吡唑并[1,5-a]二氢嘧啶和吡唑并[3,4-b]吡啶。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-05 DOI: 10.1039/d4ob01255k
Nagaraju Medishetti, Bhanu Prasad Banda, Krishnaiah Atmakur
{"title":"<i>p</i>-TSA catalyzed 6-<i>endo-trig</i>/<i>dig</i> cyclization of 5-aminopyrazoles and 3°/2°-propargylic alcohols: access to pyrazolo[1,5-<i>a</i>]dihydropyrimidines and pyrazolo[3,4-<i>b</i>]pyridines.","authors":"Nagaraju Medishetti, Bhanu Prasad Banda, Krishnaiah Atmakur","doi":"10.1039/d4ob01255k","DOIUrl":"https://doi.org/10.1039/d4ob01255k","url":null,"abstract":"<p><p>A facile, straightforward synthesis of fused pyrazolo[1,5-<i>a</i>]dihydropyrimidines and pyrazolo[3,4-<i>b</i>]pyridines is accomplished by using 5-aminopyrazoles, 3°/2°-propargylic alcohols and ynones in the presence of <i>p</i>-TSA. The reaction proceeds through allenylation (<i>N</i>-alkylation)/propargylation (<i>C</i>-alkylation) of 5-aminopyrazoles, followed by intramolecular 6-<i>endo-trig</i>/<i>dig</i> cyclization leading to the title products with the formation of new C-N and C-C bonds. Operationally simple reaction conditions, inexpensive reagents, better yields, and gram-scale synthesis are the advantages of this protocol.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142131244","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
Au(III)/TPPMS-catalyzed Friedel-Crafts benzylation of deactivated N-alkylanilines in water. Au(III)/TPPMS 催化水中失活 N-烷基苯胺的 Friedel-Crafts 苄基化反应。
IF 2.9 3区 化学
Organic & Biomolecular Chemistry Pub Date : 2024-09-05 DOI: 10.1039/d4ob01234h
Hidemasa Hikawa, Akane Fukuda, Kazuma Kondo, Taku Nakayama, Tomokatsu Enda, Shoko Kikkawa, Isao Azumaya
{"title":"Au(III)/TPPMS-catalyzed Friedel-Crafts benzylation of deactivated <i>N</i>-alkylanilines in water.","authors":"Hidemasa Hikawa, Akane Fukuda, Kazuma Kondo, Taku Nakayama, Tomokatsu Enda, Shoko Kikkawa, Isao Azumaya","doi":"10.1039/d4ob01234h","DOIUrl":"https://doi.org/10.1039/d4ob01234h","url":null,"abstract":"<p><p>The Friedel-Crafts reaction of electronically deactivated anilines including those with strong electron-withdrawing NO<sub>2</sub>, CN or CO<sub>2</sub>H groups is challenging due to the reduced electron density of the aromatic ring. Here, we demonstrate the Au(III)/TPPMS-catalyzed Friedel-Crafts benzylation of deactivated anilines in water. This reaction exhibits operational simplicity and a broad substrate scope with high regioselectivity, enabling rapid access to 2-benzylanilines.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":null,"pages":null},"PeriodicalIF":2.9,"publicationDate":"2024-09-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"142131245","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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