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Development of an operationally simple and metal-free protocol for the synthesis of 2-substituted-4-aminoquinazolines 2-取代-4-氨基喹唑啉合成方法的开发
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-08-13 DOI: 10.1016/j.tetlet.2025.155790
Vikas L. Gore, Siddiki Afsar Ali, Rohit Singh Chauhan
{"title":"Development of an operationally simple and metal-free protocol for the synthesis of 2-substituted-4-aminoquinazolines","authors":"Vikas L. Gore,&nbsp;Siddiki Afsar Ali,&nbsp;Rohit Singh Chauhan","doi":"10.1016/j.tetlet.2025.155790","DOIUrl":"10.1016/j.tetlet.2025.155790","url":null,"abstract":"<div><div>Quinazolines and its analogues are well known for pharmacophores and applications for antitumor and other areas due to their proximity to DNA bases. The development of an operationally simple and efficient method for synthesizing 4-aminoquinazolines remains a key objective in organic chemistry. In this study, we present a metal-free, straightforward protocol for the construction of 2-substituted-4-aminoquinazolines using 2-methoxy-3-nitrobenzonitrile and amidines as starting materials. This method features a practical procedure, simple work-up, and the use of cost-effective reagents, providing an efficient strategy for accessing these valuable scaffolds. All the synthesized compounds were characterised through <sup>1</sup>H NMR, <sup>13</sup>C NMR, IR and Mass spectrometry.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"170 ","pages":"Article 155790"},"PeriodicalIF":1.5,"publicationDate":"2025-08-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144828292","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
Visible light-mediated CH sulfinylalkylation of N-heteroaromatics via dimethyl sulfoxide 可见光介导的二甲基亚砜对n -杂芳烃的亚砜烷基化反应
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-08-13 DOI: 10.1016/j.tetlet.2025.155791
Lai Li , Mingyu Yang , Zhang-Jie Shi
{"title":"Visible light-mediated CH sulfinylalkylation of N-heteroaromatics via dimethyl sulfoxide","authors":"Lai Li ,&nbsp;Mingyu Yang ,&nbsp;Zhang-Jie Shi","doi":"10.1016/j.tetlet.2025.155791","DOIUrl":"10.1016/j.tetlet.2025.155791","url":null,"abstract":"<div><div>The sulfoxide moiety represents a privileged structural motif prevalent in natural products and pharmacologically active compounds. Consequently, methodologies enabling direct sulfoxide group incorporation hold significant value in contemporary drug discovery. In this work, we disclose a visible-light-driven photoredox Minisci-type reaction for the direct sulfinylalkylation of N-heteroarenes. This transformation proceeds under exceptionally mild conditions while maintaining excellent functional group tolerance, thereby offering considerable potential for late-stage diversification in medicinal chemistry applications.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"170 ","pages":"Article 155791"},"PeriodicalIF":1.5,"publicationDate":"2025-08-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144828296","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
Cyclization of aminoacetaldehyde dimethyl acetal with α-oxodithioesters in acidic media: an easy way to access 2-acylthiazoles 氨基乙醛二甲基缩醛与α-氧二硫酯在酸性介质中的环化：一种获取2-酰基噻唑的简便方法
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-08-11 DOI: 10.1016/j.tetlet.2025.155793
Kanaka Vijayashankar Honnabandar , Siddanakatte L. Prapullachandra , Nagarakere C. Sandhya , Toreshettahally R. Swaroop , Kempegowda Mantelingu
{"title":"Cyclization of aminoacetaldehyde dimethyl acetal with α-oxodithioesters in acidic media: an easy way to access 2-acylthiazoles","authors":"Kanaka Vijayashankar Honnabandar ,&nbsp;Siddanakatte L. Prapullachandra ,&nbsp;Nagarakere C. Sandhya ,&nbsp;Toreshettahally R. Swaroop ,&nbsp;Kempegowda Mantelingu","doi":"10.1016/j.tetlet.2025.155793","DOIUrl":"10.1016/j.tetlet.2025.155793","url":null,"abstract":"<div><div>In this letter, we disclose the formation of 2-acylthiazoles by the cyclocondensation of aminoacetaldehyde dimethyl acetal with α-oxodithioesters in the presence of <em>p</em>-tolunesulfonic acid in DMF at 80 °C. The present method reduces a step for the synthesis of 2-acylthiazoles from α-oxodithioesters and thus overcome the limitation of our earlier work which involves the reaction between α-oxothioamides and bromoacetaldehyde diethyl acetal. The generality of the reaction has been demonstrated in the presence of various electro neutral, electron donating and electron withdrawing groups. High overall yields and relatively shorter reaction times for some reactions are the prons of this protocol.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"170 ","pages":"Article 155793"},"PeriodicalIF":1.5,"publicationDate":"2025-08-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144828293","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
Iron-catalyzed regioselective α,α-dichlorocarbonylation of alkynes under photo-irradiation 光照射下铁催化区域选择性α，α-二氯羰基化反应
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-08-07 DOI: 10.1016/j.tetlet.2025.155786
Chen Bao, Meng Guan
{"title":"Iron-catalyzed regioselective α,α-dichlorocarbonylation of alkynes under photo-irradiation","authors":"Chen Bao,&nbsp;Meng Guan","doi":"10.1016/j.tetlet.2025.155786","DOIUrl":"10.1016/j.tetlet.2025.155786","url":null,"abstract":"<div><div>α,α-Dichlorocarbonyl core exhibited unique versatility towards a series of cyclic and acyclic scaffolds. Besides, it is ubiquitous in numerous biologically interesting products. As such, efficient and divergent synthetic methodology for achieving α,α-dichlorocarbonyl structural core under mild conditions attracted tremendous attentions so far. In this paper, an efficient route for the synthesis of α,α-dichlorocarbonyl compounds via an oxidative nucleophilic oxychlorination of alkyne under iron/photo dual catalysis is described under mild conditions.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"170 ","pages":"Article 155786"},"PeriodicalIF":1.5,"publicationDate":"2025-08-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144860531","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
Bioinspired synthesis of a lactam analogue of abyssomicin C 生物启发合成阿比索菌素C的内酰胺类似物
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-08-05 DOI: 10.1016/j.tetlet.2025.155778
A. Cole Edwards, Joshua G. Pierce
{"title":"Bioinspired synthesis of a lactam analogue of abyssomicin C","authors":"A. Cole Edwards,&nbsp;Joshua G. Pierce","doi":"10.1016/j.tetlet.2025.155778","DOIUrl":"10.1016/j.tetlet.2025.155778","url":null,"abstract":"<div><div>The bioinspired approach to abyssomicin C developed by Sorensen has been utilized to prepare a novel analog containing an α, β-unsaturated lactam. This synthesis was designed to utilize the intramolecular Diels-Alder reaction in late-stage synthesis to provide analogs that contain deep-seated modifications to explore their antimicrobial properties. Overall, installing this non-natural lactam moiety was successful and allowed for antimicrobial assessment of the analog, but the low yields highlight the frequent challenges of leveraging a bioinspired approach for a new-to-nature molecular target.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"170 ","pages":"Article 155778"},"PeriodicalIF":1.5,"publicationDate":"2025-08-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144781562","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
Gram-scale total synthesis of (+)-pseudoephedrine （+）-伪麻黄碱的克级全合成
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-08-05 DOI: 10.1016/j.tetlet.2025.155775
Shun He , Huan Yang , Hua-Cheng Xu , Cheng Zou
{"title":"Gram-scale total synthesis of (+)-pseudoephedrine","authors":"Shun He ,&nbsp;Huan Yang ,&nbsp;Hua-Cheng Xu ,&nbsp;Cheng Zou","doi":"10.1016/j.tetlet.2025.155775","DOIUrl":"10.1016/j.tetlet.2025.155775","url":null,"abstract":"<div><div>Based on the requirements of natural product total synthesis and medicinal chemistry research, we have developed a gram-scale total synthesis of (+)-pseudoephedrine [(1<em>S</em>,2<em>S</em>)-2-(<span>methylamino</span>)-1-<span>phenylpropan</span>-1-<span>ol</span>]. The strategy involves the construction of two chiral centers through Sharpless asymmetric dihydroxylation (AD) and establishment of the molecular skeleton via configuration inversion. Starting from ethyl cinnamate, (+)-pseudoephedrine was prepared on gram-scale through 11 straightforward steps with 40 % overall yield. This synthetic route features multiple one-pot reactions, requiring only two intermediate purifications throughout the entire process. The purity and absolute configuration of the target compound were confirmed by melting point analysis, specific rotation measurement, and NMR characterization.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"170 ","pages":"Article 155775"},"PeriodicalIF":1.5,"publicationDate":"2025-08-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144826355","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 of polysubstituted naphthalenes from cyclopentadienones using o-diiodobenzene/NaH as a benzyne system 邻二碘苯/萘为苄基体系由环戊二烯酮合成多取代萘
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-08-02 DOI: 10.1016/j.tetlet.2025.155774
Haojie Zhu , Ying Hu , Yiou Hu , Yan Ge , Wei Wang , Shilei Zhang , Xiaobei Chen
{"title":"Synthesis of polysubstituted naphthalenes from cyclopentadienones using o-diiodobenzene/NaH as a benzyne system","authors":"Haojie Zhu ,&nbsp;Ying Hu ,&nbsp;Yiou Hu ,&nbsp;Yan Ge ,&nbsp;Wei Wang ,&nbsp;Shilei Zhang ,&nbsp;Xiaobei Chen","doi":"10.1016/j.tetlet.2025.155774","DOIUrl":"10.1016/j.tetlet.2025.155774","url":null,"abstract":"<div><div>We present an efficient strategy for constructing polysubstituted naphthalenes through Diels-Alder cycloaddition between cyclopentadienone derivatives and benzynes. Utilizing <em>o</em>-diiodobenzene as a stable benzyne precursor in combination with sodium hydride (NaH) enables facile in situ generation of reactive benzyne intermediate. The method features operational simplicity, use of readily accessible and cost-effective raw materials and tolerance towards diverse functional groups, thereby establishing an environmentally benign platform for synthesizing polycyclic aromatic architectures with potential applications in materials science and pharmaceutical chemistry.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"170 ","pages":"Article 155774"},"PeriodicalIF":1.5,"publicationDate":"2025-08-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144763859","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
Cobalt-catalyzed hydroxymethylation of terminal alkynes 钴催化末端炔的羟甲基化
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-08-02 DOI: 10.1016/j.tetlet.2025.155761
Min Liu , Erdong Qu , Rentao Zhang , Yaoguo Huang , Peng Wang , Changkun Li
{"title":"Cobalt-catalyzed hydroxymethylation of terminal alkynes","authors":"Min Liu ,&nbsp;Erdong Qu ,&nbsp;Rentao Zhang ,&nbsp;Yaoguo Huang ,&nbsp;Peng Wang ,&nbsp;Changkun Li","doi":"10.1016/j.tetlet.2025.155761","DOIUrl":"10.1016/j.tetlet.2025.155761","url":null,"abstract":"<div><div>Primary propargylic alcohols are important synthetic intermediates in organic chemistry. We have developed a cobalt-catalyzed hydroxymethylation reaction of terminal alkynes and paraformaldehyde under neutral conditions. A variety of primary propargylic alcohols bearing different functional groups have been synthesized. The utilization of tridentate bisoxazoline-phosphine ligand and the hexafluoroisopropyl alcohol solvent are essential for the high reactivity. The mild reaction allows the one-pot synthesis of α,β-unsaturated aldehydes from terminal alkynes and paraformaldehyde via hydroxymethylation/isomerization sequence.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"170 ","pages":"Article 155761"},"PeriodicalIF":1.5,"publicationDate":"2025-08-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144756818","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
Organocatalysis and organic electrosynthesis as an alternative for zingerone preparation 有机催化和有机电合成作为姜酮制备的替代方法
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-08-01 DOI: 10.1016/j.tetlet.2025.155772
Jéssica O. Figueiredo , Emily M. Porto , Marcelo H.R. Carvalho , Daniel M. Araújo , Guilherme M. Martins , Giovanni W. Amarante , Pedro P. de Castro
{"title":"Organocatalysis and organic electrosynthesis as an alternative for zingerone preparation","authors":"Jéssica O. Figueiredo ,&nbsp;Emily M. Porto ,&nbsp;Marcelo H.R. Carvalho ,&nbsp;Daniel M. Araújo ,&nbsp;Guilherme M. Martins ,&nbsp;Giovanni W. Amarante ,&nbsp;Pedro P. de Castro","doi":"10.1016/j.tetlet.2025.155772","DOIUrl":"10.1016/j.tetlet.2025.155772","url":null,"abstract":"<div><div>This study presents a novel and efficient method for synthesizing zingerone through a combination of organocatalysis and organic electrosynthesis. The process begins with the aldol condensation of vanillin and acetone using <em>in situ</em> generated morpholinium trifluoroacetate organocatalyst. This step is followed by the electrochemical reduction of the resulting enone intermediate using a simple setup employing graphite electrodes, KBr as electrolyte and water as the proton source. This approach allows for a simple and safe strategy to access zingerone, significantly enhancing the reaction's efficiency. Notably, the method's simplicity eliminates the need for hazardous reagents and solvents, making it an environmentally friendly alternative.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"170 ","pages":"Article 155772"},"PeriodicalIF":1.5,"publicationDate":"2025-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144749020","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
New approach to the synthesis of cyazofamid, fungicide 杀菌剂氰唑胺合成的新方法
IF 1.5 4区 化学
Tetrahedron Letters Pub Date : 2025-08-01 DOI: 10.1016/j.tetlet.2025.155747
Ch. Ajay , A. Saikiran , T. Ravi Teja , B. Gopalan , B. Sridhar , B.V. Subba Reddy
{"title":"New approach to the synthesis of cyazofamid, fungicide","authors":"Ch. Ajay ,&nbsp;A. Saikiran ,&nbsp;T. Ravi Teja ,&nbsp;B. Gopalan ,&nbsp;B. Sridhar ,&nbsp;B.V. Subba Reddy","doi":"10.1016/j.tetlet.2025.155747","DOIUrl":"10.1016/j.tetlet.2025.155747","url":null,"abstract":"<div><div>A robust and versatile six-step synthetic approach has been developed for the synthesis of cyazofamid, a highly selective fungicide used for controlling <em>oomycete</em> pathogens, particularly <em>phytophthora infestans</em>, the causing agent of late blight in potatoes. The pivotal step involves the construction of an imidazole ring <em>via</em> the cyclization of 2-amino-1-(<em>p</em>-tolyl)ethan-1-one with ethyl 2,2,2-trichloroacetimidate. Other key transformations in the synthesis include the dehydration of amide to nitrile, the regioselective chlorination, and N-sulfamoylation of the imidazole ring. All the reactions are performed on a preparative scale, affording an overall yield of 28 %. This approach employs non-hazardous, readily available reagents and offers improved regioselectivity, presenting a practical advancement in the synthesis of cyazofamid.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"170 ","pages":"Article 155747"},"PeriodicalIF":1.5,"publicationDate":"2025-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144749019","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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