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Aromatizaiton of 2‐Carbonyl‐1‐Tetralones and Analogues via Aerobic Oxidation under Basic Conditions
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400458
Tianqi Wang , Fangyao Su , Shuting Yin , Boxiao Zhang , Yongguo Liu , Prof. Baoguo Sun , Prof. Hongyu Tian , Dr. Sen Liang
{"title":"Aromatizaiton of 2‐Carbonyl‐1‐Tetralones and Analogues via Aerobic Oxidation under Basic Conditions","authors":"Tianqi Wang ,&nbsp;Fangyao Su ,&nbsp;Shuting Yin ,&nbsp;Boxiao Zhang ,&nbsp;Yongguo Liu ,&nbsp;Prof. Baoguo Sun ,&nbsp;Prof. Hongyu Tian ,&nbsp;Dr. Sen Liang","doi":"10.1002/ajoc.202400458","DOIUrl":"10.1002/ajoc.202400458","url":null,"abstract":"<div><div>1‐Tetralone‐2‐carboxylates have been shown to undergo aromatization in the presence of sodium hydride under blue light irradiation in DMSO, yielding 1‐hydroxy‐2‐naphthoates with yields ranging from 30 % to 92 %. This method is also effective for the aromatization of 2‐acyl‐1‐tetralones, 1‐tetralone‐2‐carboxamides, and related structures containing heteroarenes. Thus, it serves as a valuable synthetic approach for the preparation of 2‐carbonyl substituted 1‐naphthols. The proposed mechanism involves aerobic oxidation under light irradiation, leading to the formation of <em>α</em>,<em>β</em>‐unsaturated hydroperoxide intermediates, which subsequently produce the aromatized products.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400458"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622609","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
Synthesis and Characterization of Novel Mesomorphic Chromenonapthophenathridines
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400623
Marichandran Vadivel , Swamynathan K , V. A. Raghunathan , Dr. Sandeep Kumar
{"title":"Synthesis and Characterization of Novel Mesomorphic Chromenonapthophenathridines","authors":"Marichandran Vadivel ,&nbsp;Swamynathan K ,&nbsp;V. A. Raghunathan ,&nbsp;Dr. Sandeep Kumar","doi":"10.1002/ajoc.202400623","DOIUrl":"10.1002/ajoc.202400623","url":null,"abstract":"<div><div>Heterocyclic discotic liquid crystals containing heteroatoms such as O, N, S, Se, P as part of π‐conjugated framework has revolutionized organic semiconductors research. The presence of heteroatom in π‐conjugated core has been reported to strikingly influence the self‐assembling properties. In this work we have synthesized novel chromenophenanthridines where the incorporation of oxygen facilitates the in plane ordering of central core and improves liquid crystalline character in these molecules. This paper elucidates the mesomorphic behavior of chromenonapthophenanthridines prepared via tandem Pictet Spengler cyclisation and ipso‐aromatic substitution in one pot. The synthesized compounds exhibited wide range enantiotropic columnar hexagonal phase. The mesomorphic behavior was suggested as a function of peripheral alkyl chains. The shorter homologue was found to exhibit hexagonal columnar plastic phase whereas higher ones exhibit hexagonal columnar phase.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400623"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622568","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
One‐pot Synthesis and Antitubercular Activity of Imidazo[2,1‐b]thiazol‐1H‐pyrazolylphosphonates
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400724
Nagaraju Chirra , Varshitha Shanigarapu , Balasubramanian Sridhar , Srinivas Kantevari
{"title":"One‐pot Synthesis and Antitubercular Activity of Imidazo[2,1‐b]thiazol‐1H‐pyrazolylphosphonates","authors":"Nagaraju Chirra ,&nbsp;Varshitha Shanigarapu ,&nbsp;Balasubramanian Sridhar ,&nbsp;Srinivas Kantevari","doi":"10.1002/ajoc.202400724","DOIUrl":"10.1002/ajoc.202400724","url":null,"abstract":"<div><div>Herein, we present an effective one‐pot method for the synthesis of imidazo[2,1‐<em>b</em>]thiazole‐pyrazole phosphonates from 5‐imidazo[2,1‐<em>b</em>] thiazole carboxaldehydes. The reaction involves a 1,3‐dipolar cycloaddition between <em>in situ</em> generated <em>α</em>,<em>β</em>‐unsaturated ketones and the Bestmann–Ohira reagent (BOR), facilitated by a base, leading to the formation of pyrazole phosphonates as the sole regioisomer with excellent yields. The <em>in vitro</em> evaluation of the newly synthesized compounds <strong>4(a</strong>–<strong>x)</strong> against <em>Mycobacterium tuberculosis</em> H37Rv (<em>Mtb</em>) identified compound <strong>4</strong> <strong>o</strong> as the most effective analogue (MIC: 6.25 μg/mL; 10.40 μM).</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400724"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622310","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
Recent Total Syntheses of Cephalotaxine‐Type Alkaloids and Their Structural Diversification (2021–2024): An Update
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400652
Yeju Oh , Anagha Reneesh , Hongjun Jeon
{"title":"Recent Total Syntheses of Cephalotaxine‐Type Alkaloids and Their Structural Diversification (2021–2024): An Update","authors":"Yeju Oh ,&nbsp;Anagha Reneesh ,&nbsp;Hongjun Jeon","doi":"10.1002/ajoc.202400652","DOIUrl":"10.1002/ajoc.202400652","url":null,"abstract":"<div><div>Cephalotaxine‐type alkaloids present a challenging yet rewarding target for synthetic chemists due to their intricate polycyclic structures and significant biological activity. This review consolidates recent reports (2021–2024) on the total synthesis of cephalotaxine‐type alkaloids, emphasizing innovative catalytic approaches and key transformations that enable efficient construction of the core tetracyclic framework. Advances in techniques such as asymmetric polycyclization, dual catalysis, and rearrangement strategies have streamlined synthetic routes, reducing the number of steps and enhancing stereocontrol. Additionally, structural diversification on the cephalotaxine scaffold during this period has offered valuable insights into structural modifications in medicinal chemistry and potential biosynthetic pathways. This review proposes a new structural classification of cephalotaxine‐type alkaloids. It covers ten recent total syntheses, providing detailed descriptions of the synthetic methodologies employed and comparative analyses with previous syntheses. Four reports on the structural diversification of cephalotaxines are also included.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400652"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622327","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
Transition Metal‐Free Synthesis of β‐Carboline Substituted 1,2,3‐Thiadiazoloyl Derivatives Using Elemental Sulfur as a Sulfur Source
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400485
Deepika , Dr. Ravindresh Chhabra , Prof. Ajay Bansal , Prof. Virender Singh
{"title":"Transition Metal‐Free Synthesis of β‐Carboline Substituted 1,2,3‐Thiadiazoloyl Derivatives Using Elemental Sulfur as a Sulfur Source","authors":"Deepika ,&nbsp;Dr. Ravindresh Chhabra ,&nbsp;Prof. Ajay Bansal ,&nbsp;Prof. Virender Singh","doi":"10.1002/ajoc.202400485","DOIUrl":"10.1002/ajoc.202400485","url":null,"abstract":"<div><div>A transition metal‐free, I<sub>2</sub>‐catalyzed C−S cross‐coupling reaction has been developed for the synthesis of β‐carboline substituted 1,2,3‐thiadiazoloyl derivatives using β‐carboline‐based enaminones, tosyl hydrazide, and elemental sulfur. The highlighted features of this methodology include the formation of C−S, S−N, and C−N bonds, the use of inexpensive and nontoxic catalyst, high efficiency, easy procedures, short reaction time, and generation of natural product inspired scaffolds with good to excellent yields (upto 89 %). All the synthesized β‐carboline substituted 1,2,3‐thiadiazoloyl derivatives (<strong>1</strong>–<strong>25</strong> <strong>B</strong>) were investigated for <em>in vitro</em> cytotoxicity against HeLa cell line. The compound <strong>4</strong> <strong>B</strong> emerged as the most potent anticancer agent with IC<sub>50</sub> values of 25.9 μM.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400485"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622348","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
Defluorinative Hydroxylation Promoted by Silica to Access Optically Pure Hexahydrofuranocarbazole via [4+2] Addition Reaction
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400752
Madavi S. Prasad , Thoudam Bedanta , Souvik Saha , Aman Kumar Jha , Sankar Bharani , Ponnada Chandrasekhar
{"title":"Defluorinative Hydroxylation Promoted by Silica to Access Optically Pure Hexahydrofuranocarbazole via [4+2] Addition Reaction","authors":"Madavi S. Prasad ,&nbsp;Thoudam Bedanta ,&nbsp;Souvik Saha ,&nbsp;Aman Kumar Jha ,&nbsp;Sankar Bharani ,&nbsp;Ponnada Chandrasekhar","doi":"10.1002/ajoc.202400752","DOIUrl":"10.1002/ajoc.202400752","url":null,"abstract":"<div><div>Crafting an efficient strategy for the synthesis of biologically active and functionally rich hexahydrofuranocarbazole is a highly desirable but demanding pursuit. This research elucidates a groundbreaking strategy involving an unanticipated defluorinative hydroxylation reaction facilitated by silica gel, yielding highly enantio‐ and diastereoselective hexahydrofuranocarbazole frameworks. This method results in the formation of five consecutive chiral centers, including three quaternary stereocenters and an all‐carbon spiro center, <em>via</em> an aminocatalytic asymmetric remote [4+2] addition process. The developed methodology allows for the construction of a diverse array of products (24 examples, up to &gt;99 % <em>ee</em> and 17 : 1 <em>dr</em>), reflecting its notable substrate scope. Furthermore, we demonstrate the feasibility of gram‐scale synthesis and control experiments that underscore the methodological advancements and provide insights into the underlying mechanism.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400752"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622391","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
Solvent Effects in the Reactions of Alkenes with gem‐Bis(triflyl)ethylene
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400651
Dr. Hikaru Yanai , Reon Sano , Dr. Shoki Hoshikawa , Prof. Dr. Takashi Matsumoto
{"title":"Solvent Effects in the Reactions of Alkenes with gem‐Bis(triflyl)ethylene","authors":"Dr. Hikaru Yanai ,&nbsp;Reon Sano ,&nbsp;Dr. Shoki Hoshikawa ,&nbsp;Prof. Dr. Takashi Matsumoto","doi":"10.1002/ajoc.202400651","DOIUrl":"10.1002/ajoc.202400651","url":null,"abstract":"<div><div>The reaction modes in the reactions of several alkenes with Tf<sub>2</sub>C=CH<sub>2</sub> (Tf=CF<sub>3</sub>SO<sub>2</sub>) have been controlled by the reaction solvents. For example, although the reaction with allylsilanes selectively produced normal allylation products in MeCN, <em>gem</em>‐bis(triflyl)cyclopentanes were formed in toluene. In particular, a selective formation of the (3+2) cycloadducts was achieved by using sterically hindered allylsilanes. We also found notable solvent effects in the reaction with simple alkenic hydrocarbons. That is, in hot toluene, the Alder ene reaction of the alkenes with Tf<sub>2</sub>C=CH<sub>2</sub> smoothly proceeded to give the corresponding (<em>E</em>)‐alkenes bearing a superacidic bis(triflyl)methyl group.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400651"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ajoc.202400651","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622436","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}
引用次数: 0
Origin of Regioselectivity Switch in Pyridinium Functionalizations with Phosphinoyl and Carbamoyl Radicals
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400701
Dr. Lingfei Hu , Wenyao Ding , Wei Liu , Limeng Wang , Dr. Xiangying Lv , Prof. Gang Lu
{"title":"Origin of Regioselectivity Switch in Pyridinium Functionalizations with Phosphinoyl and Carbamoyl Radicals","authors":"Dr. Lingfei Hu ,&nbsp;Wenyao Ding ,&nbsp;Wei Liu ,&nbsp;Limeng Wang ,&nbsp;Dr. Xiangying Lv ,&nbsp;Prof. Gang Lu","doi":"10.1002/ajoc.202400701","DOIUrl":"10.1002/ajoc.202400701","url":null,"abstract":"<div><div>The origins of regioselectivity switch in pyridinium phosphinoylation and carbamoylation were computationally investigated using energy decomposition analysis. The results reveal that the preference for regioselectivity arises from distinct intermolecular interactions between phosphinoyl/carbamoyl radicals and pyridinium derivatives. The ortho‐methoxy group on pyridinium remodulates different types of intermolecular interactions, exhibiting an opposite trend in its influence on para versus ortho selectivity.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400701"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622459","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
C−H Methylthiolation/d3‐Methylthiolation of Pyrazole Skeleton via Interrupted Pummerer Reaction
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400639
Haofeng Shi , Fengxia Sun , Jialiang Wu , Jiaxin He , Yuli Sun , Yunfei Du
{"title":"C−H Methylthiolation/d3‐Methylthiolation of Pyrazole Skeleton via Interrupted Pummerer Reaction","authors":"Haofeng Shi ,&nbsp;Fengxia Sun ,&nbsp;Jialiang Wu ,&nbsp;Jiaxin He ,&nbsp;Yuli Sun ,&nbsp;Yunfei Du","doi":"10.1002/ajoc.202400639","DOIUrl":"10.1002/ajoc.202400639","url":null,"abstract":"<div><div>The reaction of a series of pyrazole derivatives with DMSO/ ‐DMSO‐<em>d<sub>6</sub></em> and thionyl chloride conveniently afforded the 4‐thiolated pyrazole products under metal‐free conditions. This C−H functionalization/elelctrophilic thiolation process is postulated to involve the <em>in situ</em> generation of the electrophilic hypochlorothioite <em>via</em> interrupted Pummerer reaction, followed with the electrophilic methylthiolation of pyrazole skeleton.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400639"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622551","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
Transition Metal‐Catalyzed Transformations of Oxa/Aza Bicyclic Alkenes
IF 2.8 4区 化学
Asian Journal of Organic Chemistry Pub Date : 2025-03-01 DOI: 10.1002/ajoc.202400617
Fatemeh Doraghi , Shahab Kermaninia , Hadi Afaridoun , Bagher Larijani , Mohammad Mahdavi
{"title":"Transition Metal‐Catalyzed Transformations of Oxa/Aza Bicyclic Alkenes","authors":"Fatemeh Doraghi ,&nbsp;Shahab Kermaninia ,&nbsp;Hadi Afaridoun ,&nbsp;Bagher Larijani ,&nbsp;Mohammad Mahdavi","doi":"10.1002/ajoc.202400617","DOIUrl":"10.1002/ajoc.202400617","url":null,"abstract":"<div><div>Transition metal‐catalyzed transformations of bridged‐ring bicyclic alkenes have emerged as an interesting area of synthetic chemistry in the last two decades. Due to their multiple points of reactivity, bicyclic alkenes, especially <em>oxa</em>/<em>aza</em>‐bicyclic alkenes, can participate in a variety annulation/functionalization reactions catalyzed by transition metals. In this review, a wide range of transition metal‐catalyzed C−H activation/addition of bicyclic alkenes with nucleophiles is described.</div></div>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"14 3","pages":"Article e202400617"},"PeriodicalIF":2.8,"publicationDate":"2025-03-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143622552","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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