Article
Chemistry, Organic
Linhong Zuo, Yulian Yang, Wusheng Guo
Summary: The Pd-catalyzed decarboxylative approach allows for the modular synthesis of highly functionalized pyrroles using cyclic carbonates and amines as reaction partners, with only CO2 and H2O generated as byproducts. Operating at room temperature and in open air, this method is ideal for the derivatization of bioactive compounds. Mechanistic investigations have shown that the stereoselective formation of the (Z)-configured gamma-amino ketone intermediate is crucial for the success of the reaction.
Article
Chemistry, Applied
Dirgha Raj Joshi, Ikyon Kim
Summary: The study successfully achieved multi-functionalization of the pyridine motif in indolizine through [5+1] annulative construction, introducing three different functional groups at the C5, C6, and C7 positions. The solvent (2-MeTHF) and the hydroxyl of 2-hydroxyacetophenones were found to play crucial roles in the successful cyclization event. Furthermore, the elaboration of the resulting scaffold and the potential expansion using other methyl ketones were also demonstrated.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Li Chen, Jin-Mei Qi, Shu Yang, Si-Nuo Sun, Sheng-Jiao Yan
Summary: We have developed a new method to synthesize functionalized chromeno[2,3-c]pyrrol-9(1H)-one derivatives (CMPOs) 3 and 3' from 3-formylchromones by reacting with proline derivatives. This strategy involves a cascade reaction that occurs by simply heating a mixture of substrates 1 with 2 and toluene, followed by oxidation with oxygen and catalysis by CuBr. In a single step, this protocol cleaves two bonds (2 C-C) and forms three bonds (1 C-N and 2 C-C bonds) to produce a range of CMPOs 3 and 3'. This method can be used to synthesize functionalized CMPOs for combinatorial and parallel syntheses in a one-pot reaction.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Biochemistry & Molecular Biology
Shaoren Yuan, Gabriel Guerra Faura, Hailey E. Areheart, Natalie E. Peulen, Stefan France
Summary: A Lewis acid-catalyzed intramolecular ring-opening benzannulation of 5-(indolyl)2,3-dihydrofuran acetals is reported. The resulting 1-hydroxycarbazole-2-carboxylates are formed in up to 90% yield within 1 hour. The dihydrofuran acetals can be easily accessed from the reactions of enol ethers and alpha-diazo-beta-indolyl-beta-ketoesters. The synthetic utility of this method is demonstrated through a formal total synthesis of murrayafoline A, a bioactive carbazole-containing natural product.
Article
Chemistry, Multidisciplinary
Omekolsoom Sheibani, Sayed Hossein Banitaba
Summary: Performing organic reactions with solid nano-catalysts has been a focus of research recently. A one-step tandem strategy for the diastereoselective synthesis of rel-(2R,3R)-2-benzoyl-2,3-dihydro-3-substitutedphenyl-4H-furo[3,2-c][1]benzopyran-4-one has been developed. This protocol uses SiO2 nanoparticles as a non-metal oxide catalyst for the solvent-free condensation of aromatic aldehydes, 4-hydroxycoumarin, and in situ generated phenacyl pyridinium bromide. The protocol is environmentally friendly, rapid, and has high yields with low catalyst loading, no extensive workup procedures or chromatographic separations required, and the catalyst can be recycled multiple times without significant loss of activity.
Article
Chemistry, Physical
Jian-Shu Wang, Jiangjie Zhang, Siqi Wang, Jun Ying, Chuan-Ying Li, Xiao-Feng Wu
Summary: A novel palladium-catalyzed domino carbonylative cyclization has been developed for the rapid construction of functionalized heterocycles. The reaction proceeds smoothly with the consecutive formation of C-C and C-X bonds using benzene-1,3,5-triyl triformate as the CO source, yielding a variety of biologically relevant derivatives.
JOURNAL OF CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Scott W. Spring, Jesse H. Hsu, Renee J. Sifri, Szu-Ming Yang, Chloe S. Cerione, Tristan H. Lambert, Christopher J. Ellison, Brett P. Fors
Summary: Creating strong and tough plastics from sustainable and biorenewable resources is a significant challenge. In this study, we synthesized a thermoplastic material, poly(2,3-dihydrofuran) (PDHF), using a metal-free cationic polymerization process. PDHF exhibited high tensile strength, toughness, optical clarity, and barrier properties, making it suitable for various applications.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Multidisciplinary
Xia Chen, Cheng Zhong, Yuling Lu, Meng Yao, Zhenhua Guan, Chunmei Chen, Hucheng Zhu, Zengwei Luo, Yonghui Zhang
Summary: A practical and efficient method has been developed for the synthesis of fluorescent 2,3-naphthalimide derivatives via an intramolecular didehydro-Diels-Alder reaction. The methodology shows wide substrate scope, good functional group tolerance and practicality for gram-scale synthesis of environmentally sensitive fluorophores with shorter time, fewer steps and less waste disposal. Experimental and computational studies support the crucial role of the propiolimide moiety in the transformation.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Pavel A. Topanov, Anna A. Maslivets, Maksim V. Dmitriev, Irina V. Mashevskaya, Yurii V. Shklyaev, Andrey N. Maslivets
Summary: A novel heterocyclic compound has been synthesized using a simple method. This compound exhibits antimicrobial and antibiofilm activities.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Su Chen, Monica Oliva, Luc Van Meervelt, Erik V. Van der Eycken, Upendra K. Sharma
Summary: The study presents a palladium-catalyzed cascade reaction to construct difunctionalized acyl indoles, involving multiple bond formations in a single operational step. Enantioselectivity at a quaternary carbon center is attempted. Additionally, a continuous-flow process is demonstrated for the synthesis of aryl isocyanides within minutes and their telescopic use.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Jiao-Jiao Han, Tao Jiang, Cui Zhang, Dan-Dan Cui, Yuan-Zhao Hua, Guang-Jian Mei, Min-Can Wang, Shi-Kun Jia
Summary: The enantioselective [3 + 2] annulation of α-hydroxy-1-indanones with yne-enones was achieved using dinuclear zinc catalysts via a Bronsted base and Lewis acid cooperative activation model. A variety of enantioenriched spiro[2,3-dihydrofuran-2,2'-inden-1-one] derivatives were obtained with high yields, excellent diastereoselectivities, and enantiostereoselectivities (up to 84% yield, 20:1 dr, 99% ee). This method offers a broad substrate scope, gram-scale synthesis, and late-stage functionalization of complex molecules.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
T. T. Wen, L. Z. Wang
Summary: A magnetic core-shell copper-based nanocatalyst was successfully prepared and characterized using various analytical techniques. The highly efficient catalyst exhibited excellent catalytic activity and selectivity in the one-pot synthesis of diester/methyl-substituted polycyclic fused 1,5-benzodiazepines. The catalyst's easy recovery and reusability, along with its practicality, environmental friendliness, and economic attractiveness, make it a promising candidate for various applications.
MATERIALS TODAY CHEMISTRY
(2022)
Article
Chemistry, Organic
Biwei Zhang, Hongjian Yang, Taimin Wang, Xuanzhen Han, Haiyan Sun, Lijing Fang, Hongbin Zhai, Bin Cheng
Summary: The microwave-promoted multicomponent reaction successfully synthesized SH-chromeno[2,3-d]pyrimidin-5-one derivatives in good to excellent yields under catalyst-free and solvent-free conditions. This unexpected annulation pathway further expanded the synthetic application of paraformaldehyde as a C1 building block.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Qingsong Deng, Aimin Yu, Shunguang Zhang, Xiangtai Meng
Summary: A novel tunable domino reaction promoted by K2CO3 was developed for the synthesis of benzothiophene fused pyranone and thiochromen fused furan derivatives by adjusting MgSO4. The reaction involves C-S bond cleavage induced by K2CO3 followed by two-step condensation reactions. The significance of these novel domino reactions lies in the production of products that are not easily accessible via traditional synthetic methods.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Yoshifumi Hashikawa, Shumpei Sadai, Yasujiro Murata
Summary: Amino-functionalized cage-opened [60]-fullerene derivatives were synthesized by reactions with phenylenediamine, showing high-lying highest occupied molecular orbital levels and intense near-infrared absorption bands. The reaction involves direct addition of the diamine to the alpha,beta-unsaturated carbonyl moiety and further C-C bond scission promoted by intramolecular S(N)2 reaction.
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
