Heptafluorobutyric Acid Catalyzed Cross-Dehydrogenative Coupling of 7-Aminocoumarins with 1,2,4-Triazines: A Straightforward Pathway to 3-Triazinyl-7-aminocoumarins
Synthesis DOI: 10.1055/s-0042-1751570 A protocol for C–H/C–H cross-coupling reaction between 7-aminocoumarins and 1,2,4-triazines has been developed. The reaction was carried out under heptafluorobutyric acid catalysis providing products with yield up to 91%. The applicability and scope of the proposed method was demonstrated on 25 compounds containing different substituents both in the triazine ring and at the nitrogen atom of 7-aminocoumarins. The study of the reaction mechanism by EPR and radical trapping suggests that radicals are involved in this transformation. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 704...
Source: Synthesis - March 1, 2024 Category: Chemistry Authors: Fatykhov, Ramil F. Khalymbadzha, Igor A. Sharapov, Ainur D. Potapova, Anastasia P. Tsmokalyuk, Anton N. Gaviko, Vasiliy S. Tags: paper Source Type: research
Synthesis of the Cyclohexane Fragment Peculiar to Enacyloxins: Study of Its Assembly and Protective Groups Removal
Synthesis DOI: 10.1055/s-0042-1751567 The enantioselective synthesis of the protected (1S,3R,4S)-3,4-dihydroxycyclohexane-1-carboxylic acid moiety shared among all members of the enacyloxin family has been successfully accomplished. Having obtained this fragment, we devised assembly conditions using models that mimic the enacyloxin acyl chain. Additionally, we assessed conditions for the removal of protective groups, aiming to avoid previously reported detrimental ester shifts. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents | Abstract | Fu...
Source: Synthesis - March 1, 2024 Category: Chemistry Authors: Christin, Orane Roulland, Emmanuel Tags: paper Source Type: research
Preparations of Silyl Anions
Conclusions [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - February 29, 2024 Category: Chemistry Authors: Pulikkottil, Feba T. Balakrishnan, Venkadesh Chandrasekaran, Revathi Murugesan, Vetrivelan Rasappan, Ramesh Tags: review Source Type: research
Phosphazene-Catalyzed Regioselective Condensation of Allyl Thioethers with Aldehydes: A Rapid Approach to 1,3-Dienyl Sulfides, -Sulfoxides and -Sulfones
Synthesis DOI: 10.1055/a-2259-5395 The phosphazene-catalyzed regioselective condensation of allyl thioethers with aldehydes is investigated. Upon treatment of allyl thioethers with P4-t-Bu, allyl thioether anions are generated and rapidly react with aromatic aldehydes, leading to 1,3-dienyl sulfides in good yields with high regioselectivity. This finding provides an alternative approach for the preparation of allyl thioether anions in a regioselective manner. In addition, chemoselective transformations of 1,3-dienyl sulfides to provide the corresponding 1,3-dienyl sulfoxides or 1,3-dienyl sulfones are also demonstrated. [....
Source: Synthesis - February 27, 2024 Category: Chemistry Authors: Phae-nok, Supasorn Kuhakarn, Chutima Leowanawat, Pawaret Reutrakul, Vichai Soorukram, Darunee Tags: paper Source Type: research
A Simple and Efficient Approach for the Synthesis of Aryl-3-(trifluoromethyl)-1H-1,2,4-triazol-5(4H)-one Derivatives
Synthesis DOI: 10.1055/a-2254-0712 In this work, a series of 4-aryl-3-(trifluoromethyl)-1H-1,2,4-triazol-5(4H)-one derivatives is synthesized through nucleophilic intramolecular cyclization reactions of ethyl 2-(2,2,2-trifluoro-1-(arylimino)ethyl)hydrazine-1-carboxylate intermediates, which are themselves prepared in high yields via reactions of ethyl chloroformate and N-aryl-2,2,2-trifluoroacetimidoyl chloride derivatives. Some of the merits of the reported procedure are an operationally simple and concise method, the ready availability of starting materials, excellent product yields, no formation of harmful by-products a...
Source: Synthesis - February 27, 2024 Category: Chemistry Authors: Kazemi, Elham Zeinali, Najmeh Darehkordi, Ali Tags: paper Source Type: research
Emerging Trends in Glycoscience
Synthesis 2024; 56: 887-889 DOI: 10.1055/s-0042-1752048 [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - February 27, 2024 Category: Chemistry Authors: Tiwari, Vinod K. Tags: editorial Source Type: research
Linked PDF of Table of Contents
Synthesis 2024; 56: V- DOI: 10.1055/s-0040-1720109 Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents (Source: Synthesis)
Source: Synthesis - February 27, 2024 Category: Chemistry Tags: table of contents Source Type: research
Stereochemical Aspects of the C-Glycosylation of Pyranosides and Furanosides
Conclusion [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents | Abstract | Full text (Source: Synthesis)
Source: Synthesis - February 26, 2024 Category: Chemistry Authors: Achanta, Srinivas Sasikala, Ch. V. A. Basu, Debjit Nahide, Pradip D. Bandichhor, Rakeshwar Tags: review Source Type: research
Visible-Light-Driven Oxidative Chlorination of Alkyl sp3 C –H Bonds with HCl/Air at Room Temperature
Synthesis DOI: 10.1055/a-2261-3255 An aerobic chlorination of alkyl sp3 C–H bonds of functionalized alkanes and simple alkanes has been established successfully under visible light at room temperature. The reaction is performed in the presence of catalytic NaNO2 using HCl or NaCl/acid as a chlorine source and air as a terminal oxidant under atmospheric pressure. It is suggested that NOCl from NaNO2/HCl is a crucial species in the catalytic cycle involving an aerobic oxidation and a photochemical radical chlorination. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Tab...
Source: Synthesis - February 26, 2024 Category: Chemistry Authors: Xu, Lai Mei, Chong Lu, Wenjun Tags: paper Source Type: research
Synthesis of Anti-oxidant Steroids by Hybridisation with Nitroxides
Synthesis DOI: 10.1055/a-2232-8240 Steroidal–nitroxide hybrid molecules and non-radical controls were synthesised in good yields using simple carbodiimide coupling. An unexpected product arose from reactions between the nitroxide moiety and the solvent THF. Methoxyamine derivatives of the nitroxide drug hybrids were produced using Fenton chemistry without side reactions occurring on the steroid. The hybrid compounds bind to the glucocorticoid receptor and are relevant for the study of radical biological chemistry and redox-related disease processes. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, German...
Source: Synthesis - February 26, 2024 Category: Chemistry Authors: Soltau, Carl P. Weir, Naomi E. Martyn, Alexander P. Bottle, Steven E. Tags: paper Source Type: research
Generation of Alkylidene Carbenes through Tetrazole Fragmentation: Recent Advances and Applications in Organic Synthesis
Synthesis DOI: 10.1055/a-2260-5652 Tetrazole fragmentation under mild conditions from 5-hydroxyalkyl-1H-tetrazoles (HATs) or cyanophosphates (CPs) readily generates the corresponding alkylidene carbenes, which undergo [1,2]-rearrangements or [1,5]-C–H insertions to yield one-carbon homologous alkynes or five-membered unsaturated carbocycles, respectively. Furthermore, azido-HATs and 2-cyanoazetidines afford propargylic and homopropargylic amines, respectively, via [1,2]-rearrangement of the corresponding aminoalkyl alkylidene carbenes. These reactions are successfully applied for the synthesis of various biofunctional mo...
Source: Synthesis - February 22, 2024 Category: Chemistry Authors: Harusawa, Shinya Yoneyama, Hiroki Usami, Yoshihide Tags: short review Source Type: research
Hypervalent Iodine Mediated Synthesis of Thiosulfonates from Sulfonyl Hydrazides and Their Transformation into Symmetrical Disulfides
Synthesis DOI: 10.1055/a-2260-0346 A transition-metal-free synthesis of thiosulfonates has been accomplished by the disproportionate coupling of readily available and inexpensive sulfonyl hydrazides embracing hypervalent iodine(III) [phenyliodine(III) diacetate (PIDA)] as an oxidant. This synthesis involves cleavage of the S–N bond and is endowed with creation of a new S–S bond. The thiosulfonates were further reduced with CS2/KOH to obtain symmetrical disulfides. This protocol features mild reaction conditions in open air, an inexpensive oxidant, and high functional group tolerance with good to excellent product yield...
Source: Synthesis - February 22, 2024 Category: Chemistry Authors: Yadav, Ashvani Kumar, Rohit Prasad, Virendra Tags: paper Source Type: research
Iron-Catalyzed [2+1+2+1] Annulation of Amines and N,N-Dimethyl Enaminones using N,N-Dimethylaminoethanol as a One-Carbon Synthon for the Synthesis of 1,4-Dihydropyridines
Synthesis DOI: 10.1055/a-2241-2196 A simple and efficient method for the synthesis of 1,4-dihydropyridines from amines, N,N-dimethyl enaminone and N,N-dimethylaminoethanol in a four-component [2+1+2+1] annulation catalyzed by FeCl3 has been established, where N,N-dimethylaminoethanol was applied as a methine source. The procedure was executed smoothly, resulting in the synthesis of a wide range of 1,4-dihydropyridines with moderate to good yields. Additionally, these fluorophores exhibited good photophysical characteristics. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournal...
Source: Synthesis - February 22, 2024 Category: Chemistry Authors: Ma, Wanqian Kuang, Qiulin Li, Suzhen Guo, Mengyi Song, Yibo Cheng, Luoteng Yuan, Jianyong Tags: paper Source Type: research
Synthesis, Photophysical, and AIE Properties of 2H-Imidazole-Derived Push-Pull Fluorophores
Synthesis DOI: 10.1055/s-0042-1751561 A four-stage method for the synthesis of 2H-imidazole-derived push-pull fluorophores was developed. The synthesized compounds are characterized by absorption in the range of 250–400 nm, emission of up to 617 nm, and quantum yields of up to 99%. Compounds bearing a tetraphenylethylene fragment demonstrated the AIE effect in a solution with a water fraction fw >90% and significant increase in the emission intensity of up to 20 times and quantum yields of up to 22%. The ICT states for these fluorophores were confirmed by calculating the excited state dipole moments (>23D). The rep...
Source: Synthesis - February 22, 2024 Category: Chemistry Authors: Lavrinchenko, Igor A. Nikiforov, Egor A. Moseev, Timofey D. Varaksin, Mikhail V. Tsmokalyuk, Anton N. Nechaev, Thomas V. Charushin, Valery N. Chupakhin, Oleg N. Tags: paper Source Type: research
Synthesis of Alkyl Thiochromano[2,3-c]pyrrole-9-carboxylate Derivatives Utilizing Benzo[b]thiofuran-2,3-dione, Maleimides, and Alkyl Alcohol/Water Mixtures
Synthesis DOI: 10.1055/a-2260-0420 A set of thiochromano[2,3-c]pyrrolidine-1,3-diones, incorporating α-hydroxy esters and their acids at the C-9 position, was prepared via direct interaction involving benzo[b]thiofuran-2,3-diones, maleimides, and alkyl alcohols in water at 90 °C. Structures of the new products were deduced from HRMS and NMR spectral data and confirmed by single-crystal X-ray crystallography. An insight into a proposed pathway involving a sequential Michael conjugate addition (initiated by the sulfur atom) and an aldol-type reaction is presented. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stut...
Source: Synthesis - February 22, 2024 Category: Chemistry Authors: Abadleh, Mohammed M. Zahra, Jalal A. Sabri, Salim S. Abuzaid, Rania R. Schollmeyer, Dieter El-Abadelah, Mustafa M. Tags: paper Source Type: research
