Article
Chemistry, Organic
Arpine Vardanyan, Alexander Villinger, Peter Ehlers, Peter Langer
Summary: A new and convenient method for synthesizing aryl-substituted naphtho[2,1-a]azulenes by combining Suzuki-Miyaura, Sonogashira, and cycloisomerization reactions is reported. This methodology was used to synthesize previously unknown azuleno[1,2-h]quinolines, cyclohepta[1,2]indeno[4,5-b]thiophenes, and cyclohepta[1,2]indeno[4,5-c]thiophenes. The impact of different fused heterocyclic rings on the photophysical and electrochemical properties of these azulene derivatives was studied using experimental and theoretical methods, providing a rationale for the preparation of novel azulene derivatives with improved properties for organic material applications.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Chaorong Wang, Zhencheng Lai, Hujun Xie, Sunliang Cui
Summary: This study demonstrated the use of triazenyl alkynes as versatile building blocks in multicomponent reactions, leading to the synthesis of beta-amino amides with high diastereoselectivity and structural diversity. The bifunctionality of triazenyl alkynes, acting as both C2 fragment and directing group, played a crucial role in achieving the desired outcomes. Furthermore, the triazenyl group allowed for diverse late-stage transformations, opening up new possibilities for building block discovery and rational design of MCRs.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Organic
Yulia A. Trukhanova, Nikita M. Chernov, Elena V. Kuvaeva, Igor P. Yakovlev
Summary: This article comprehensively reviews the progress in C,N-diarylformamidine chemistry and covers the research findings from 1999 to 2022. The research indicates that synthesizing complex molecules through the modification of C,N-diarylformamidine compounds can potentially expand the range of drugs.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Wen-Shuai Dong, Yong Hu, Zu-jia Lu, Chao Zhang, Xiaowei Wu, Jian-Guo Zhang
Summary: The design of energetic compounds usually focuses on achieving the plane effect to obtain compounds with high density, high thermal stability, and low sensitivity. A four-ring energetic compound was efficiently designed and synthesized by a clever intramolecular cyclization strategy. The compound exhibits excellent performance with good thermal stability, mechanical sensitivity, and positive heat of formation.
CRYSTAL GROWTH & DESIGN
(2023)
Review
Chemistry, Physical
Nilanjana Majumdar
Summary: Catalytic asymmetric transformation is a powerful strategy for synthesizing diverse nonracemic molecular entities. Carboxylic acids have been explored as building blocks in this area, and significant advancements have been made in the last three decades. They can act as both C- and O-nucleophiles, as well as electrophiles, in asymmetric reactions under catalytic conditions.
Article
Engineering, Environmental
Sanaz Daneshmand-Jahromi, Davood Karami, Nader Mahinpey
Summary: In this study, a high surface area alumina support was synthesized using a mixed solvent system of toluene-dimethylformamide (DMF) and aluminum precursors. The specific surface area of the alumina support was optimized at a Toluene/DMF volume ratio of 0.4 and reached about 1000 m(2)/g after vacuum drying at 200 degrees C. By varying the calcination temperature, different mesoporous alumina supports with varying pore sizes were obtained. The preparation of high surface area alumina was attributed to the simultaneous hydrolysis and condensation of the alkoxides and careful slow drying in the toluene-DMF system.
JOURNAL OF ENVIRONMENTAL CHEMICAL ENGINEERING
(2022)
Review
Biochemistry & Molecular Biology
Dmitriy Yu Vandyshev, Khidmet S. Shikhaliev
Summary: Building heterocyclic systems with hydrogenated fragments is crucial for creating biologically-active compounds. N-substituted maleimides play a special role in this process, but their use in cascade heterocyclization reactions is currently limited.
Article
Chemistry, Multidisciplinary
Chuanyong Wang, Qingliang Yang, Yuan-Hao Dai, Jianqi Xiong, Yu Zheng, Wei-Liang Duan
Summary: This study presents the first nickel-catalyzed synthesis of P-stereogenic secondary aminophosphine-boranes through the asymmetric addition of primary phosphines to azo compounds. The versatility of these synthesized P-stereogenic compounds allows for the facile synthesis of both known and novel P-stereogenic compounds through sequential and stereospecific reactions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Sheng Zhang, Ziyang Wang, Ya Gao, Masahiko Yamaguchi, Ming Bao
Summary: This article describes the first palladium-catalyzed remote C-H dimethylamination of 1-chloromethylnaphthalenes using N,N-dimethylformamide as the dimethylamino source. The dimethylamination occurred exclusively at the 4-position of 1-chloromethylnaphthalenes in 2-methyltetrahydrofuran under mild conditions, resulting in good to high yields of 1-(N,N-dimethylamino)-4-alkylnaphthalenes. The halogen atom remained intact during the dimethylamination process. A conveniently synthesized and successfully utilized P,N bidentate ligand was employed in the Kumada-Corriu reaction.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Lorena Rico, Da Li, Stephen Hanessian
Summary: In this study, we described a stereocontrolled synthesis method for 2,3-alpha-methano tetrahydrofurans using a TFA-mediated reaction. Various substituents were prepared in good yields and could be easily derivatized, providing a series of chiral compounds with potential applications in medicinal chemistry.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Alessandro Brusa, Debora Iapadre, Maria Edith Casacchia, Alessio Carioscia, Giuliana Giorgianni, Giandomenico Magagnano, Fabio Pesciaioli, Armando Carlone
Summary: Asymmetric organocatalyzed multicomponent reactions are an important tool in organic synthesis for constructing complex scaffolds from simple starting materials. The Enders three-component cascade reaction was a cornerstone in this field, followed by numerous organocatalyzed cascade reactions. In this study, we successfully utilized acetaldehyde dimethyl acetal as a masked form of acetaldehyde in the Enders-type cascade reaction, allowing for the conversion of acetaldehyde, nitroalkenes, and enals into cyclohexenals with high stereochemical density and excellent enantioselectivity.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Mathematical & Computational Biology
Yuewu Liu, Mengfang Zeng, Shengyong Liu, Chun Li
Summary: Virus assembly is a crucial step in virus replication and offers potential drug targets. This process involves the polymerization of virus structural protein monomers into building blocks, which then assemble into virus shells. In this study, we developed five dynamical models to describe the synthesis reactions for different types of building blocks. We proved the existence and uniqueness of positive equilibrium solutions for each model and analyzed the stability of these equilibrium states. Our results suggest that the concentration of dimer building blocks decreases as the ratio of off-rate constant to on-rate constant increases. Similarly, trimer building blocks decrease with an increasing ratio of off-rate constant to on-rate constant. These findings provide insights into the dynamic properties of virus-building block synthesis in vitro.
MATHEMATICAL BIOSCIENCES AND ENGINEERING
(2023)
Article
Chemistry, Organic
Mohamed Abdel-Rady, Mahmoud H. Mahross, Abu-Bakr A. El-Adasy, Ahmed A. Atalla, Ahmed A. Khames, Abdel Haleem M. Hussein
Summary: Reaction of arylhydrazones with different reagents lead to various derivatives, such as pyrazole derivatives. The theoretical calculations agreed with experimental data, providing insight into the properties of the synthesized compounds.
SYNTHETIC COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Carl Recsei, Yaniv Barda
Summary: A new procedure for synthesizing a side-product present in the herbicide pyroxasulfone was reported in this study, which involved constructing a bis(aryloxy)fluoromethane moiety for which no existing method was available.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Yi Ling Hu, Qi Zhang, Shuang He Liu, Jia Li Sun, Fang Zhou Yin, Zi Ru Wang, Jing Shi, Rui Hua Jiao, Hui Ming Ge
Summary: Terpenoids are a diverse family of natural products, with plants and fungi being the main sources. However, bacteria have been reported to produce a relatively small number of terpenoids. Recent genomic data suggests that many biosynthetic gene clusters encoding terpenoids in bacteria remain uncharacterized. In this study, a Streptomyces chassis-based expression system was selected and optimized to enable the functional analysis of terpene synthase and related enzymes. Through genome mining, 16 bacterial terpene biosynthetic gene clusters were chosen, with 13 successfully expressed in the Streptomyces chassis. This led to the characterization of 11 terpene skeletons, including three new ones, representing an approximately 80% success rate. Additionally, the expression of tailoring genes resulted in the isolation and characterization of 18 novel terpenoids. The use of the Streptomyces chassis facilitated the production and modification of bacterial terpenoids.