Article
Multidisciplinary Sciences
Luo Ge, Esther G. Sinnema, Juana M. Perez, Roxana Postolache, Marta Castineira Reis, Syuzanna R. Harutyunyan
Summary: This study reports a general methodology for the selective synthesis of functionalized chiral Z-alkenes. The method utilizes readily available alkene-derived phosphines as an alternative to alkylating reagents in Wittig olefination, offering new retrosynthetic disconnections for the formation of functionalized disubstituted alkenes. The potential of this method is demonstrated by structural diversification of several bioactive molecules.
Article
Chemistry, Applied
Xiang Shi, TianTian Xia, Brooke E. McKamey, Xian Wu, Yue Sun, Weifeng Zhou, Guangyan Zhang
Summary: In this study, an efficient synthesis of [6]-paradol was achieved in four steps with a 72.0% overall yield. The method utilized commercially available materials and allowed for convenient isolation with multiple crystallization without the need for column chromatography, resulting in a high-purity product of over 99.2% purity that is suitable for large-scale synthesis.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2021)
Editorial Material
Chemistry, Multidisciplinary
Moumita Majumdar
Summary: Monomeric stibine oxide has been difficult to obtain due to the large antimony orbitals and the high electronegativity difference with oxygen. However, a free tris(2,6-diisopropylphenyl)stibine oxide has been isolated and can serve as an oxo-transfer reagent.
Article
Biochemistry & Molecular Biology
Ana Donaire-Arias, Martin L. Poulsen, Jaime Ramon-Costa, Ana Maria Montagut, Roger Estrada-Tejedor, Jose I. Borrell
Summary: Chalcones, a type of molecule that can be easily synthesized through aldol condensation, lacks standard procedures and often yields low purity and low yields. By comparing aldol condensation and Wittig reaction, the improved procedure of Wittig reaction shows high yield and excellent purity, providing a novel method for the synthesis of chalcones.
Article
Chemistry, Organic
Toshiki Yamashiro, Keisuke Tokushige, Takumi Abe
Summary: The paper presents an unprecedented method for synthesizing indolines with an N3-quinazolin-2,4-dione moiety using an AZIN. The concise synthesis involves a tandem Staudinger/chemo-selective azaWittig/cyclization sequence of AZINs with isatoic anhydride by a one pot protocol.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Evgeny M. Buev, Polina A. Khardina, Vladimir S. Moshkin, Vyacheslav Y. Sosnovskikh
Summary: In this study, a multicomponent synthesis of pyrrolidines was performed using a Wittig/Huisgen tandem reaction, which allows the simultaneous generation of alkene and azomethine ylide from the same carbonyl compound. This approach successfully constructed highly substituted dispiropyrrolidines as well as simple 3-substituted pyrrolidines.
TETRAHEDRON LETTERS
(2022)
Review
Chemistry, Organic
Keyvan Pedrood, Mohammad Nazari Montazer, Bagher Larijani, Mohammad Mahdavi
Summary: This review summarizes recent studies on heterocyclic compounds focusing on the formation of the C=N bond via the aza-Wittig reaction. It also discusses two different strategies for forming heterocyclic compounds and provides up-to-date information on the synthesis of various N-containing heterocyclic compounds using the aza-Wittig reaction in chemical literature since 2010.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Abel Idrice Adjieufack, Benoit Champagne, Vincent Liegeois
Summary: Bonding evolution theory was used to elucidate the reaction mechanism of the intramolecular aza-Wittig reaction. The reaction involves the formation of a cycloadduct, decarboxylation, intramolecular [2+2] cycloaddition, and retro [2+2] cycloaddition. The rate-determining step is the formation of the cycloadduct and the reaction is exergonic, resulting in the formation of the aromatic benzothiazole.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Tatsuaki Hori, Shuya Kakinuma, Naoya Ohtsuka, Takeshi Fujinami, Toshiyasu Suzuki, Norie Momiyama
Summary: The Wittig reaction was used to synthesize 2,3,5,6-tetrafluoro-4-halostyrene (TFXSs) as functional monomers with halogen-bond donor sites. The reaction was efficiently carried out in tetrahydrofuran using 1,1,3,3-tetramethylguanidine as an organic base. Correlation analysis identified three key factors for obtaining TFXSs in reasonable yields. This study contributes to the field of halogen-bond-based functional molecules and explores digitalization as a potential strategy in small-molecule synthesis.
Article
Chemistry, Organic
Petrakis N. Chalikidi, Taimuraz T. Magkoev, Andrey V. Gutnov, Oleg P. Demidov, Maxim G. Uchuskin, Igor V. Trushkov, Vladimir T. Abaev
Summary: Two approaches have been developed for the synthesis of substituted phosphonium salts from easily available benzyl alcohols and their heterocyclic analogs. The direct mixing method is more efficient for acid-sensitive substrates, while the one-pot procedure is better for benzyl alcohols with electroneutral or electron-withdrawing substituents.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yannan Liu, Shuai Fu, Dominik L. Pastoetter, Arafat Hossain Khan, Yingying Zhang, Arezoo Dianat, Shunqi Xu, Zhongquan Liao, Marcus Richter, Minghao Yu, Miroslav Polozij, Eike Brunner, Gianaurelio Cuniberti, Thomas Heine, Mischa Bonn, Hai Wang, Xinliang Feng
Summary: The ability to efficiently synthesize vinylene-linked two-dimensional covalent organic frameworks (V-2D-COFs) is crucial for their potential applications in electronics and optoelectronics. In this study, the E/Z selectivity of the Wittig reaction was tailored by using a suitable catalyst and increasing the reaction temperature, resulting in the successful synthesis of four crystalline V-2D-COFs. The high charge carrier mobilities and good crystallinity of these V-2D-COFs were demonstrated through non-contact terahertz spectroscopy analysis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Polymer Science
Gauthier Desmaizieres, Martin E. Speer, Inna Thiede, Philipp Gaiser, Verena Perner, Martin Kolek, Peter Bieker, Martin Winter, Birgit Esser
Summary: Organic redox polymers show promise as electrode materials for rechargeable batteries, with dibenzo[a,e]cyclooctatetraene (DBCOT) identified as a particularly attractive redox-active group. The synthesis of aliphatic DBCOT-polymers and their electrochemical properties were investigated, demonstrating their potential as battery electrode materials. Further research is needed to optimize electrode composition and fabrication processes to fully utilize the redox activity of DBCOT polymers.
MACROMOLECULAR RAPID COMMUNICATIONS
(2021)
Review
Biochemistry & Molecular Biology
Gheorghe Ilia, Vasile Simulescu, Nicoleta Plesu, Vlad Chiriac, Petru Merghes
Summary: Carbonyl olefinations are important organic syntheses for forming C=C bonds, often with high yields and excellent stereoselectivity. The Wittig reaction is a well-known carbonyl olefination method, involving the reaction between an aldehyde or ketone and a Wittig reagent. The use of ultrasound in these reactions, including modified Wittig syntheses, has been studied for green synthesis and improved yields and reaction times.
Article
Chemistry, Organic
Mingxian Xu, An Chen, Zhilin Ren, Jiying Qiu, Mingming Zu, Yi Zhang, Jiayi Wang, Ping He
Summary: The one-pot synthesis of azide-substituted dihydropyrazoles in isopropanol was successfully achieved, followed by investigation of Staudinger-aza-Wittig-dehydroaromatization reactions with methyl(diphenyl)phosphine for further application in the construction of pyrazolo[1,5- c ]quinazolines.
Article
Chemistry, Organic
Simona Fazekasova, Jozef Gonda, Miroslava Martinkova, Martina Bago Pilatova, Monika Majirska, Veronika Turcanova, David Jager
Summary: A short synthetic route towards novel cytotoxic FTY720 analogues with variously substituted azo-benzene units was developed. The target compounds were constructed using Wittig olefination or Mills reaction as key processes. Preliminary biological screening showed promising antiproliferative activity of the newly synthesised derivatives against Jurkat, HeLa, and HCT-116 cells, comparable or higher than cisplatin. The structure-activity relationship indicated that the loss of the alkyl side chain or its substitution with a hydroxymethyl group on the azobenzene core seemed to be detrimental for the resulting cytotoxic profile. To probe the photochromic properties, the reversible E/Z isomerization and thermal relaxation rate of the final derivatives were determined.
Article
Chemistry, Applied
Javier Mazuela, Thomas Antonsson, Laurent Knerr, Stephen P. Marsden, Rachel H. Munday, Magnus J. Johansson
ADVANCED SYNTHESIS & CATALYSIS
(2019)
Article
Chemistry, Organic
Scott Rice, Daniel J. Cox, Stephen P. Marsden, Adam Nelson
Article
Biochemistry & Molecular Biology
Robert A. Lowe, Dale Taylor, Kelly Chibale, Adam Nelson, Stephen P. Marsden
BIOORGANIC & MEDICINAL CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Daniel Francis, Adam Nelson, Stephen P. Marsden
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Chemistry, Organic
John P. Cooksey, Ourida Saidi, Jonathan M. J. Williams, A. John Blacker, Stephen P. Marsden
Summary: Valuable tetrahydro-beta- and gamma-carboline skeletons can be obtained through Pictet-Spengler cyclization initiated by acceptorless dehydrogenation of saturated cyclic amines. The substrate scope for beta-isomers is somewhat limited, but access to gamma-isomers through the more reactive 2-(aminoethyl)indoles is more general. The synthetic utility of hydrogen transfer catalysis is highlighted in the two-step preparation of the alkaloid desbromoarborescidine A by sequential redox-neutral alkylation/dehydrogenative cyclization.
Article
Chemistry, Applied
Daniel Francis, A. John Blacker, Nikil Kapur, Stephen P. Marsden
Summary: The new modular photochemical continuous stirred-tank reactor (CSTR) design utilizes light-source units developed for the fReactor CSTR platform, making it suitable for both homogeneous and multiphasic reactions. By using slurries as input feeds, the system intensifies photochemical brominations, and its modular nature facilitates the integration of downstream reaction steps.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2022)
Article
Chemistry, Medicinal
Chloe Townley, Lindsay McMurray, Stephen P. Marsden, Adam Nelson
Summary: A top-down synthetic approach was used to efficiently synthesize 21 diverse novel molecular scaffolds, which were derived from complex intermediates prepared using cycloaddition chemistry. Scaffold-hopping of these intermediates was achieved through ring attachment, cleavage, expansion, and/or fusion, leading to the generation of diverse lead-like screening compounds.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2022)
Article
Chemistry, Organic
Tarn C. Johnson, Stephen P. Marsden
Summary: A convenient and simple three-component synthesis of substituted pyridylacetic acid derivatives is reported. The method utilizes the dual reactivity of Meldrum's acid derivatives, first as nucleophiles to substitute activated pyridine-N-oxides, and then as electrophiles with a range of nucleophiles to induce ring-opening and decarboxylation.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Anthony Aimon, Mark J. Dow, Abigail R. Hanby, Ephraim A. Okolo, Christopher M. Pask, Adam Nelson, Stephen P. Marsden
Summary: The stereocontrolled synthesis of complex spirotricyclic systems containing an embedded syn-1,2-diaminocyclohexane unit is achieved through a dearomatising oxidation of phenols bearing pendant ureas capable of acting as double nucleophiles. The resultant products possess rich functionality suitable for the synthesis of potentially bioactive compounds.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Ephraim A. Okolo, Axel Pahl, Sonja Sievers, Christopher M. Pask, Adam Nelson, Stephen P. Marsden
Summary: A 'top down' scaffold remodelling approach was used to synthesize a library of spirotricyclic ureas via complexity-generating oxidative dearomatisation. Eighteen structurally distinct, sp(3)-rich scaffolds were obtained from the parent tricycle through ring addition, cleavage, and expansion strategies. Biological screening of the compound library based on these scaffolds revealed diverse phenotypic responses, highlighting both functional and structural diversity of the compounds.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Alexandra Hindle, Krzysztof Baj, Jonathan A. Iggo, Daniel J. Cox, Christopher M. Pask, Adam Nelson, Stephen P. Marsden
Summary: A convergent approach to diazabicyclic scaffolds containing twisted amides or anilines is achieved through photocatalysed hydroamination and subsequent cyclisation of cyclic enecarbamates. The modular synthesis enables variation of the degree of twist and consequently the properties of the amides and anilines.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Mary E. Bayana, J. Steven Wailes, Stephen P. Marsden
Summary: A two-step process has been developed to rapidly access diverse tri- and tetrasubstituted pyridines by utilizing a range of reactants.
Article
Chemistry, Multidisciplinary
Samuel D. Griggs, Alejandro Martin-Roncero, Adam Nelson, Stephen P. Marsden
Summary: This study reports a regioselective gamma-C-H amination method for the side-chain of saturated 2-alkyl nitrogen heterocycles, which proceeds through a sulfamide-directed 1,6-radical translocation. The practicality of this rapid access to 1,3-diamines is highlighted in a short synthesis of the alkaloid tetraponerine T8 and non-natural analogues.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Scott Rice, Daniel J. Cox, Stephen P. Marsden, Adam Nelson
Summary: Regioselective and stereospecific directed C-H arylation of simple amine substrates, followed by cyclisation, resulted in the synthesis of 30 diverse, three-dimensional scaffolds. This unified approach significantly expanded the range of bridged ring systems containing both a nitrogen atom and an aromatic ring.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Alexandre F. Trindade, Emily L. Faulkner, Andrew G. Leach, Adam Nelson, Stephen P. Marsden
CHEMICAL COMMUNICATIONS
(2020)
