Tetrahedron Green Chem最新文献

{"title":"Deep eutectic solvent mediated synthesis of β-carbolines and related natural products via Pictet–Spengler reaction and aerobic oxidation","authors":"Bhuvana Narasimman","doi":"10.1016/j.tgchem.2025.100082","DOIUrl":"10.1016/j.tgchem.2025.100082","url":null,"abstract":"<div><div>An eco-friendly, one-pot synthesis of <em>β</em>-carboline derivatives using deep eutectic solvent is reported. This protocol utilizes commercially available aldehydes and tryptamine, involving Pictet–Spengler cyclization followed by aerobic oxidation. This environmentally friendly methodology offers access to various <em>β</em>-carboline alkaloids Nitramarine, Nitraridine, Eudistomin U, Norharmane, Harmane, and their analogues in a single step with 30–68% yields.</div></div>","PeriodicalId":101215,"journal":{"name":"Tetrahedron Green Chem","volume":"6 ","pages":"Article 100082"},"PeriodicalIF":0.0,"publicationDate":"2025-12-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144611702","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Laccase cataylzed synthesis of quaternary malononitriles with an aryl substituent","authors":"Parisa Amani,&nbsp;Mansour Shahedi,&nbsp;Elaheh Rezaei,&nbsp;Zohreh Habibi","doi":"10.1016/j.tgchem.2025.100066","DOIUrl":"10.1016/j.tgchem.2025.100066","url":null,"abstract":"<div><div>Synthesis of quaternary malononitriles with an aryl substituent is of great importance because these scaffolds serve as essential intermediates in the synthesis of bioactive compounds. This study presents an efficient method for the laccase-catalyzed arylation of 2-substituted malononitrile derivatives by oxidation of catechols using aerial oxygen as the oxidant, followed by the nucleophilic addition of 2-substituted malononitriles. The process achieves yields ranging from moderate to excellent (73–97 %), and also, it was associated with a slight decrease in efficiency in higher scales.</div></div>","PeriodicalId":101215,"journal":{"name":"Tetrahedron Green Chem","volume":"5 ","pages":"Article 100066"},"PeriodicalIF":0.0,"publicationDate":"2025-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143096432","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Solvent-free and eco-friendly green protocol for N-Boc Protection of amines using picric acid as a catalyst","authors":"Ramesha Thongolla ,&nbsp;Ummareddy Venkata Subba Reddy ,&nbsp;Sailam Sri Gogula ,&nbsp;Empati Raja Sekhar ,&nbsp;Puchakayala Muralidhar Reddy ,&nbsp;Anren Hu","doi":"10.1016/j.tgchem.2024.100061","DOIUrl":"10.1016/j.tgchem.2024.100061","url":null,"abstract":"<div><div>We have developed an environmentally conscious green protocol to protect amine functional groups in drug discovery and the total synthesis of biologically active natural products. This method utilizes di-<em>tert</em>-butyl dicarbonate ((Boc)₂O) to protect aromatic and aliphatic amines, with readily available picric acid (2 mol%) serving as a Brønsted acid catalyst. This approach enables rapid and high-yield (up to 98 %) protection of amines under completely solvent-free and eco-friendly conditions, thereby promoting a cleaner and more sustainable synthetic process.</div></div>","PeriodicalId":101215,"journal":{"name":"Tetrahedron Green Chem","volume":"5 ","pages":"Article 100061"},"PeriodicalIF":0.0,"publicationDate":"2025-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143096510","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Selective synthesis of phosphate mono-esters with an acidic modified niobium oxide catalyst","authors":"Jens Wéry,&nbsp;Sofia Radelicki,&nbsp;Thomas J.N. Hooper,&nbsp;Margot Houbrechts,&nbsp;Kwinten Janssens,&nbsp;Wouter Stuyck,&nbsp;Dimitrios Sakellariou,&nbsp;Dirk E. De Vos","doi":"10.1016/j.tgchem.2025.100063","DOIUrl":"10.1016/j.tgchem.2025.100063","url":null,"abstract":"<div><div>The atom-efficient esterification of phosphoric acid was investigated for the selective synthesis of phosphate mono-esters using an acid treated niobium oxide catalyst, avoiding the use of amines as is common in literature. Kinetic studies revealed that the heterogeneous catalyst exhibited higher selectivity for mono-esters compared to homogeneous acid catalysts, as supported by calculation of the relative reactivity of mono-ester and phosphoric acid with different catalysts. To characterize the catalyst, its Hammett acidity value (H₀) was determined, while solid state ³¹P NMR enabled studying the adsorption of H₃PO₄. Due to the mild acidity of the niobium oxide, alcohols with acid-sensitive functions, including substituted double bonds, could be phosphorylated, enabling the synthesis of surfactants such as oleyl phosphate.</div></div>","PeriodicalId":101215,"journal":{"name":"Tetrahedron Green Chem","volume":"5 ","pages":"Article 100063"},"PeriodicalIF":0.0,"publicationDate":"2025-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143096512","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Catalytic macrocyclization of unactivated C(sp3)-H bond in natural product synthesis","authors":"Zhuo Wang","doi":"10.1016/j.tgchem.2025.100064","DOIUrl":"10.1016/j.tgchem.2025.100064","url":null,"abstract":"<div><div>Macrocyclic natural products present as essential scaffolds in drug development. Excited by the biological properties of macrocyclic natural products, its synthesis and the development of macrocyclization methods is an important research area in organic and medicinal chemistry. In particular, macrocyclization preparing macrocyclic structures <em>via</em> catalytic functionalization of unactivated C(sp³)-H bonds is increasingly prevalent in the literature. Here, we provide a <em>minireview</em> highlighting the contemporary advancements of catalytic macrocyclization of unactivated C(sp³)-H bond in method developments and natural product synthesis. Representative examples from 2017 to 2024 are discussed.</div></div>","PeriodicalId":101215,"journal":{"name":"Tetrahedron Green Chem","volume":"5 ","pages":"Article 100064"},"PeriodicalIF":0.0,"publicationDate":"2025-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143096433","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Photoinduced oxidative cyclization of dithienylarenes","authors":"Barnabás Zsignár-Nagy ,&nbsp;Viktória Kümmel ,&nbsp;Tamás Gazdag ,&nbsp;Péter J. Mayer ,&nbsp;Zsófia Bokor ,&nbsp;Tamás Holczbauer ,&nbsp;Gábor London","doi":"10.1016/j.tgchem.2025.100076","DOIUrl":"10.1016/j.tgchem.2025.100076","url":null,"abstract":"<div><div>A photoinduced electrocyclization followed by aerobic oxidation of 1,2-dithienylarene derivatives is described as a greener alternative to direct aryl-aryl couplings. The formation of the naphthodithiophene type products was monitored by UV–vis spectroscopy. Naphthodithiophenes with different structural features and electronic characters were accessed. Oxidative cyclization using the combination of BF₃·Et₂O and DDQ was a complementary approach to confirm the formation of the desired products. The method was also applicable to 2,3-dithienylbiphenylene having a backbone with antiaromatic character.</div></div>","PeriodicalId":101215,"journal":{"name":"Tetrahedron Green Chem","volume":"5 ","pages":"Article 100076"},"PeriodicalIF":0.0,"publicationDate":"2025-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143800673","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"An ultrasound based greener approach to 1-chloropyrrolo[1,2-a]quinoxalines as potential anti-tubercular agents","authors":"Jyothi Shivanoori ,&nbsp;Mallesham Baldha ,&nbsp;Sunder Kumar Kolli ,&nbsp;Ravikumar Kapavarapu ,&nbsp;Manojit Pal","doi":"10.1016/j.tgchem.2025.100080","DOIUrl":"10.1016/j.tgchem.2025.100080","url":null,"abstract":"<div><div>Compounds containing the 1-chloropyrrolo[1,2-<em>a</em>]quinoxaline framework were assessed against <em>Mtb</em>CM (chorismate mutase) for the identification of possible anti-tubercular entities. These compounds were synthesized <em>via</em> the sonochemical chlorination of pyrrolo[1,2-<em>a</em>]quinoxalines using <em>N</em>-chlorosaccharin. The regioselective C-1 chlorination, mild and eco-friendly conditions, and decreased reaction time are the key aspects of the present ultrasound-assisted method, an application of which is also demonstrated. The molecular docking of synthesized compounds into the target protein <em>MtbCM</em> revealed that they were oriented in the loop region of <em>Mtb</em>CM and mostly interacted with the residues in the periphery of the loop <em>via</em> hydrophobic interactions e.g. (i) pi-sigma with LEU130 and LEU65, (ii) pi-anion with ASP69 and (iii) pi-cation with ARG134. Furthermore, similar molecular alignment of -Cl group displaying a hydrophobic interaction with PRO66 was noted in case of majority of these compounds. The compound <strong>3b</strong>, <strong>3f</strong>, <strong>3g</strong> and <strong>3k</strong> showed better binding affinities with the order <strong>3b &gt; 3f &gt; 3g</strong> &gt; <strong>3k</strong> indicating <strong>3b</strong> as the best among them. This observation correlated the outcome of <em>in vitro</em> assay using <em>Mtb</em>CM when <strong>3b</strong>, <strong>3f</strong> and <strong>3g</strong> showed &gt;50 % inhibition at 30 μM. The Structure-Activity-Relationship (SAR) suggested that the C-4 aryl/heteroaryl group seemed to be vital for the activity. Indeed, a <em>p</em>-substituent on the C-4 phenyl ring was found to be favorable for activities. The role of Cl group was also assessed <em>via in vitro</em> testing of compounds with and without –Cl group. With the IC₅₀ value 12.34 ± 0.76 μM for <em>Mtb</em>CM, the compound <strong>3b</strong> was also expected to exhibit acceptable pharmacokinetic properties.</div></div>","PeriodicalId":101215,"journal":{"name":"Tetrahedron Green Chem","volume":"5 ","pages":"Article 100080"},"PeriodicalIF":0.0,"publicationDate":"2025-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"144195313","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Valorization of saffron waste as a natural source of 3-hydroxy-γ-butyrolactone, a valuable chiral building block for pharmaceutical applications","authors":"M. Corti ,&nbsp;S. Princiotto ,&nbsp;M. Zuccolo ,&nbsp;G. Beretta ,&nbsp;S. Dallavalle ,&nbsp;A. Pinto ,&nbsp;F. Annunziata ,&nbsp;G. Borgonovo","doi":"10.1016/j.tgchem.2025.100069","DOIUrl":"10.1016/j.tgchem.2025.100069","url":null,"abstract":"<div><div>Saffron is the most expensive spice, appreciated in the best cuisine all over the world. However, its production is connected to the generation of a high volume of waste, i.e. stamens, leaves, tepals, spathes, corm, and tunics. Several biologically active compounds and high value chemical have been identified in the saffron biomass extracts, among which is found 3-hydroxy-γ-butyrolactone (3-HBL), a chiral building block involved in the production of different active pharmaceutical ingredients. The development of the first green and scalable extractive methodology for the isolation of 3-HBL from saffron tepals and stamen could be of great interest for different chemical sectors. After the selection of the best extractive medium (ethyl acetate) and the optimization of the operative procedure to a two-step protocol, microwave assisted extraction and accelerated solvent extraction were compared. The results showed a 3.6 ± 0.2 % vs 2.1 ± 0.1 % w/w recovery and could be exploitable not only on a lab scale but also for a possible industrial application. An enantiomeric excess of 14 % of the (<em>S</em>)-(−) isomer was found.</div></div>","PeriodicalId":101215,"journal":{"name":"Tetrahedron Green Chem","volume":"5 ","pages":"Article 100069"},"PeriodicalIF":0.0,"publicationDate":"2025-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143488713","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"A review on synthesis of β-amino carbonyl compounds using nanocatalyst","authors":"Satyaranjan Behera","doi":"10.1016/j.tgchem.2025.100065","DOIUrl":"10.1016/j.tgchem.2025.100065","url":null,"abstract":"<div><div>Nanomaterials have piqued researchers' interest in various fields due to their extraordinary advantages, which include a large surface area. The use of nanomaterials in catalysis is a hot issue for researchers. Catalysis plays a vital role in the synthesis of medicinal as well as pharmaceutical compounds. Pharmaceutical chemicals, including β-amino carbonyl compounds and their derivatives, are commonly used as synthetic intermediates in manufacturing natural products, pharmaceuticals, physiologically active molecules, and medicines. Synthesis of β-amino carbonyl compounds involves many processes, including Mannich and aza-Michael reactions. The synthesis of β-amino carbonyl compounds remains challenging for chemists due to their severe side products. Researchers have now used nanocatalysts to achieve clean and smooth reactions, high purity of products, and reusability. Due to high surface area, nanocatalysts have tremendous catalytic activity. Nowadays many modified nanocatalyst have been developed to produce high yields of the products. The present review described the synthesis of β-amino carbonyl compounds by using different nanocatalysts reported to date.</div></div>","PeriodicalId":101215,"journal":{"name":"Tetrahedron Green Chem","volume":"5 ","pages":"Article 100065"},"PeriodicalIF":0.0,"publicationDate":"2025-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143096509","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}

{"title":"Advanced approach to O-alkyl/aryl salicylaldehyde derivatives: Synthesis, characterization, and free-radical homopolymerization for improved thermal stability","authors":"Aashna Perwin,&nbsp;Nasreen Mazumdar","doi":"10.1016/j.tgchem.2025.100072","DOIUrl":"10.1016/j.tgchem.2025.100072","url":null,"abstract":"<div><div>In the development of bioactive materials centered around salicylaldehyde, we synthesized O-alkyl/aryl derivatives through the etherification of the phenolic group. Salicylaldehyde underwent a copper-catalyzed reaction with various halides under basic conditions, yielding 2-(3-chloropyrazin-2-yl)oxy benzaldehyde, 2-(6-chloropyrimidin-4-yl)oxy benzaldehyde, and 3-(2-formylphenoxy)-2-hydroxypropyl methacrylate. Meanwhile, 2-(2-formylphenoxy)ethyl methacrylate was synthesized via a sonication-assisted Mitsunobu reaction, affording high yields of ether derivatives. Structural elucidation was achieved using standard analytical techniques, such as ¹H NMR, ¹³C NMR, FT-IR and LC-MS. The free radical homopolymerization of 3-(2-formylphenoxy)-2-hydroxypropyl methacrylate using benzoyl peroxide as an initiator was successfully achieved. The resulting polymer exhibited enhanced thermal stability, as confirmed by solid-state ¹³C NMR, FT-IR, TGA, DSC, and SEM analyses, with a higher glass transition temperature than the reported poly(glycidyl methacrylate). This increase in <em>T</em>_<em>g</em> is attributed to the enhanced rigidity introduced by the aromatic ring in the homopolymer. This study highlights the successful synthesis of various O-alkyl/aryl salicylaldehyde derivatives using different techniques and functionalities, followed by the effective polymerization of one of the monomers, 3-(2-formylphenoxy)-2-hydroxypropyl methacrylate.</div></div>","PeriodicalId":101215,"journal":{"name":"Tetrahedron Green Chem","volume":"5 ","pages":"Article 100072"},"PeriodicalIF":0.0,"publicationDate":"2025-06-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":null,"resultStr":null,"platform":"Semanticscholar","paperid":"143550885","PeriodicalName":null,"FirstCategoryId":null,"ListUrlMain":null,"RegionNum":0,"RegionCategory":"","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":"OA","EPubDate":null,"PubModel":null,"JCR":null,"JCRName":null,"Score":null,"Total":0}