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Synlett 2024; 35: VII- DOI: 10.1055/s-0043-1763689 Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents (Source: Synlett)
Source: Synlett - February 27, 2024 Category: Chemistry Tags: table of contents Source Type: research
Cluster Preface: Biomimetic Synthesis
Synlett 2024; 35: III-IV DOI: 10.1055/s-0043-1763681
Jun Deng (left) received his B.Sc. from Lanzhou University and his Ph.D. from the Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences (2014) with Professor Ang Li. After a short period of postdoctoral research in the lab of Professor Andrew Myers at Harvard University (2014–2016), he was appointed a Pioneer ‘Hundred Talents Program’ Researcher at Kunming Institute of Botany, Chinese Academy of Sciences in 2017. In December 2020, he moved to Nankai University where he is a professor at the College of Chemistry. He received the Thieme Journals...
Source: Synlett - February 27, 2024 Category: Chemistry Authors: Deng, Jun Tang, Yefeng Tags: cluster Source Type: research
Br ønsted Acid Catalyzed Stereospecific Dearomative Spirocyclization of Benzothiophenyl Analogues of Tertiary cis-β-Benzylstyrenes
Synlett DOI: 10.1055/a-1894-8726 3-Substituted benzothiophenyl analogues of tertiary cis-β-benzylstyrenes undergo triflic acid catalyzed dearomative spirocyclization at room temperature to afford compounds containing vicinal quaternary centers. Hydroarylation of the styrene is a competing process that occurs preferentially within substrates possessing electron-rich styrenyl alkenes, or an indole in place of the benzothiophene. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents | Abstract | Full text (Source: Synlett)
Source: Synlett - February 26, 2024 Category: Chemistry Authors: Tohti, Anargul Lerda, Victoria Stokes, Benjamin J. Tags: letter Source Type: research
Facile In Situ Difluoromethylation of Phenols and Thiols Using Ethyl Bromodifluoroacetate and K2CO3
Synlett DOI: 10.1055/s-0042-1751564 Herein, we report an efficient method to access difluoromethyl ethers of thiols and phenols using ethyl bromodifluoroacetate and K2CO3. This method demonstrates chemoselective difluoromethylation of thiols and phenols in the presence of amines. The current method also discloses the synthesis of bis(aryloxy)fluoromethane compounds which are least reported in the literature. Mechanistic investigations revealed that the reaction proceeds through a nucleophilic substitution pathway. We strongly believe this protocol would offer an efficient alternative to earlier photocatalyzed or radical-me...
Source: Synlett - February 26, 2024 Category: Chemistry Authors: Dond, Bharat D. Chavan, Vijay P. Thore, Shivaji N. Tags: letter Source Type: research
Ultrasound-Mediated Green Synthesis of Imidazo[1,2-a]pyridines and Imidazo[2,1-b]thiazoles through C(sp3) –H Functionalization
Synlett DOI: 10.1055/s-0042-1751565 An ultrasound-assisted expedient protocol has been developed for the synthesis of imidazo[1,2-a]pyridines and imidazo[2,1-b]thiazoles by the C–H functionalization of ketones using a KI/tert-butyl hydroperoxide catalytic system. The reaction takes place in water, a green solvent, and does not require a metal catalyst; it also gives good yields of the products. The method offers numerous noteworthy characteristics, including mild reaction conditions, the absence of a base, broad functional-group compatibility, and excellent reaction yields. Moreover, it avoids the use of costly and air-s...
Source: Synlett - February 26, 2024 Category: Chemistry Authors: Chauhan, Swati Verma, Pratibha Srivastava, Vandana Tags: letter Source Type: research
Current Strategies on the Enantioselective Synthesis of Modified Nucleosides
Conclusion [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents | Abstract | Full text (Source: Synlett)
Source: Synlett - February 23, 2024 Category: Chemistry Authors: Mondal, Samir Kumar Mahto, Birkishore Pal, Shantanu Chandra, Girish Tags: letter Source Type: research
Synthesis and Antibacterial Studies of Phenethylamine Alkaloid Natural Products Along with Their Analogues: Discolin A, B, E and Bacillimidazole B
Synlett DOI: 10.1055/a-2256-5509 The first total synthesis of phenethylamine alkaloid based natural products discolin A, B, E and bacillimidazole B is reported, which were isolated from marine sea bacteria Tenacibaculum discolor sv11 and marine sponge. Total syntheses of discolin A, B, E and bacillimidazole B are achieved in two linear steps including condensation reaction and N-alkylation reaction with an overall yield of 68%, 35%, 65%, and 32%, respectively. A total of 24 analogues are prepared with moderate to excellent yield. All the natural products and their analogues were screened for antibacterial activity. The mos...
Source: Synlett - February 23, 2024 Category: Chemistry Authors: Khatua, Rashmi Ranjan Ahmad, Sarwat Asma Ziya Das, Susmita Anindya, Roy Khan, Faiz Ahmed Tags: letter Source Type: research
Spectroscopic Investigation of the Remote C –H Allylation of Amides via Photoredox and Nickel Dual Catalysis
Synlett DOI: 10.1055/a-2259-3594 The mechanistic details of a reported allylation reaction are investigated by means of Stern–Volmer experiments and nanosecond transient absorption spectroscopy. Both reference substrates, i.e., an allylic chloride and a trifluoroacetamide, are inefficient quenchers but large quenching rate constants are observed upon the addition of Ni(COD)2 and a bisoxazoline ligand. The large quenching rate constants and absence of observable photoproducts are consistent with a mechanism that operates by energy transfer between the excited-state iridium photosensitizer and the nickel complex. [...] Geo...
Source: Synlett - February 23, 2024 Category: Chemistry Authors: Bourgois, C éline De Kreijger, Simon Xu, Bin Tambar, Uttam K. Troian-Gautier, Ludovic Tags: letter Source Type: research
Accessing Reactive Metal Hydrides through Designed Heterometallic Bridges
Synlett DOI: 10.1055/a-2264-9040 A methodology to access reactive hydride moieties is highly desirable, yet limited. Multimetallic hydride fragments are notable for their heightened reactivity and catalysis, but deliberate access to these species is lacking. In this highlight, we discuss recent developments by our group in the design of a new heterometallic complex that invokes an architecture designed to provide modular access to reactive hydride moieties by leveraging metal hydrides in combination with pendent donors to a model heterotrimetallic Ni–(Al–H)2 complex. An amplification of insertion-based reactivity has b...
Source: Synlett - February 22, 2024 Category: Chemistry Authors: Gonzalez, Fernando De Leon, Edgardo Shoshani, Manar M. Tags: synpacts Source Type: research
An Efficient Access to Heteroaryl/Aryl-Annulated Pyridine Derivatives and a Study of Their Mosquito Larvicidal Activity Against Dengue Vector
We report a convergent synthesis of heteroaryl/aryl-annulated pyridine and quinoline derivatives by a metal-free Povarov reaction. para-Toluene sulfonic acid was used as the catalyst in this reaction, which produced the products in good yields from the corresponding aromatic amines and ethyl vinyl ether. A pyridocoumarin and a pyridopyrimidine product were evaluated for their mosquito larvicidal activity against the third instar larvae of the dengue vector mosquito Aedes aegypti. Examination of morphological changes in the larvae showed damage to the target body part after treatment with both the pyridocoumarin and pyridop...
Source: Synlett - February 22, 2024 Category: Chemistry Authors: Pal, Pamela Show, Sayanti Das, Sukanya Bhakta, Sayantika Mondal, Swarupa Roy, Priya Ghosh, Tapas Nandi, Raj K. Tags: letter Source Type: research
Regiocontrolled Halogen Dance and In Situ Transmetalation of Pyrroles Directed by the α-Substituent
Synlett DOI: 10.1055/a-2236-1060 Multiply substituted pyrroles are found in medicines, natural products, and functional materials. A general method for introducing functionality on the pyrrole ring is thus required. Herein, a regiocontrolled halogen dance reaction and an in situ transmetalation of α-functionalized bromopyrroles are reported. Selective generation of the isomeric pyrrolylmetal species was achieved by using an ethyl ester or a phenyl group at the α-position of the pyrrole and by switching between the halogen dance reaction and in situ transmetalation. These reactions proceeded smoothly when an N,N-dimethyls...
Source: Synlett - February 22, 2024 Category: Chemistry Authors: Matsuyama, Daichi Okumi, Tatsuki Mori, Atsunori Okano, Kentaro Tags: letter Source Type: research
Synthesis of Heterocycles by a C –C Cross-Coupling/Alkyne-Carbonyl-Metathesis Strategy
Synlett DOI: 10.1055/s-0042-1751513 The present article presents a personal account on the synthesis of heterocycles by the combination of regioselective Pd-catalyzed cross-coupling reactions of polyhalogenated heterocycles, i.e., Suzuki–Miyaura and Sonogashira reactions, with alkyne-carbonyl-metathesis (ACM) reactions. The products, which show interesting optical, electronic or medicinal properties, are not readily available by other methods. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents | Abstract | Full text (Source: Synlett)
Source: Synlett - February 22, 2024 Category: Chemistry Authors: Langer, Peter Tags: account Source Type: research
New Heterocyclic Organosulfur Compounds Derived from Dithioacetals
Synlett DOI: 10.1055/a-2259-3689 The dithioacetalization of lactaldehyde derivatives with ethane-1,2-, propane-1,3-, butane-1,4-, and pentane-1,5-dithiols in the presence of 4 mol% of scandium triflate has been described. A series of cyclic dithioacetals were obtained with yields ranging from quantitative to 37%. The dithioacetalization of lactaldehyde derivatives with butane-1,4-dithiol and pentane-1,5-dithiol groups are accompanied by the formation of 14- and 16-membered macrocyclic sulfur structures with yields of 3% and 18%, respectively. In the case of a cyclic dithioacetal derivative with three methylene groups, a di...
Source: Synlett - February 20, 2024 Category: Chemistry Authors: Leja, Dawid T. Depa, Wojciech J. Gu ńka, Piotr A. Zachara, Janusz Lechowicz, Jaromir B. Groszek, Grazyna Tags: letter Source Type: research
Development of an Efficient Synthetic Process for Irisquinone
Synlett DOI: 10.1055/s-0042-1751560 Irisquinone is a tumor radiotherapy sensitizer and has been found to have broad-spectrum antitumor activity in recent years. The current acquisition method of extracting and purifying from semen irisis has greatly limited its wide application and activity study deeply. In this work an efficient route for the synthesis of the irisquinone was investigated to solve the source of it. The target compound was synthesized by 5-step reactions to Wittig reaction, reduction, oxidation, Wittig reaction, and oxidation using 3,5-dimethoxycarboxaldehyde as the starting material with an overall yield o...
Source: Synlett - February 16, 2024 Category: Chemistry Authors: Zheng, Kun Zhang, Qifeng Ma, Yuheng Liang, Guodong Zhao, Yan Ga, Lu Tags: letter Source Type: research
Palladium-Catalyzed α-Arylation of Meyers’s Chiral Bicyclic Lactams and a Deprotonative Ring-Opening Sideline
Synlett DOI: 10.1055/a-2258-3788 Described is a deprotonative α-arylation reaction of Meyers’s chiral bicyclic lactams (MCBLs) under palladium catalysis, and a substrate-dependent post-transformation. When the bridgehead carbon of the MCBLs is substituted with a methyl or an ethyl group, the initial arylation product undergoes a further rearrangement reaction to give a conjugated framework. On the other hand, substrates bearing a bridgehead isopropyl or aryl group are converted into the corresponding exo-arylation products. Preliminary studies indicated that the rearrangement pathway was promoted by deprotonation and wa...
Source: Synlett - February 16, 2024 Category: Chemistry Authors: Chiang, Hsin-Lun Zhao, Wei-Ting Chen, Yi-An Lin, Yi-Ching Chen, Pei-Lin Wu, Yen-Ku Tags: letter Source Type: research
