Article
Chemistry, Multidisciplinary
Nan-Nan Mo, Yu-Hang Miao, Xiao Xiao, Yuan-Zhao Hua, Min-Can Wang, Lihua Huang, Guang-Jian Mei
Summary: In this study, the chiral phosphoric acid-catalyzed asymmetric intermolecular formal [3+2] cycloaddition of azoalkenes with azlactones has been achieved, leading to the facile and highly enantioselective construction of a wide range of fully substituted 4-pyrrolin-2-ones with a fully substituted carbon atom in good yields and excellent enantioselectivities.
CHEMICAL COMMUNICATIONS
(2023)
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)
Review
Chemistry, Applied
Dimitris Matiadis
Summary: 2-Pyrazolines are important five-membered heterocycles with two adjacent nitrogen atoms. They have various functional groups and unique biological properties, and are used as building blocks. In recent years, there has been significant progress in the synthesis of 2-pyrazolines, with the development of novel strategies and improvements of existing protocols. This review summarizes the synthetic methodologies from 2012 to 2022, discussing the challenges, capabilities, scopes, and limitations of the reactions, as well as substitution patterns and mechanisms where applicable.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Jiaxu Tang, Yuhai Tang, Xiaonan Wang, Yongzhuang Wang, Xiaoli Huang, Silong Xu, Yang Li
Summary: This study presents an efficient regioselective and stereoselective cascade annulation of indoles with alkynediones via Cp*Rh-III-catalyzed indole C2-H activation using N-carboamide directing groups, providing valuable intermediates for the total synthesis of related indole alkaloids. The methodology offers a novel and straightforward approach to the synthesis of free (NH) tetrahydrocarbazoles and pyridoindolones with continuous quaternary carbons in good to excellent yields and wide substrate scope, demonstrating the C2 and C3 difunctionalization of indoles in one-pot.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Applied
Chima E. Anyaegbu, Haonan Zhang, Jian Xiao, Minli Tao, Ning Ma, Wenqin Zhang
Summary: Polyacrylonitrile fiber supported bisquaternary ammonium salts were successfully synthesized and used as catalysts for the synthesis of various compounds. Among the prepared fiber catalysts, PAN(BQAc)F showed the best catalytic activity and can be used for multiple runs with only a slight decrease in catalytic activity.
REACTIVE & FUNCTIONAL POLYMERS
(2022)
Article
Chemistry, Organic
Chada Raji Reddy, Uprety Ajaykumar, Amol D. Patil, Remya Ramesh
Summary: A CAN-promoted oxidative ipso-cyclization of unactivated biaryl ynones with S-centered radicals has been developed for the synthesis of spiro[5,5]trienones. The method exhibited excellent regioselectivity towards spirocyclization and tolerated various functional groups. Dearomatization of previously unknown aryl/heteroaryl groups was also achieved. DMSO was employed as a low-toxicity, inexpensive solvent and oxygen source.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Huawei Lin, Xianru Yang, Wenyue Ning, Xiaofang Huang, Xiaoqun Cao, Yanqing Ge, Biming Mao, Chang Wang, Hongchao Guo, Chunhao Yuan
Summary: Nitrogen-containing heterocycles play crucial roles in biologically active natural products and pharmaceuticals, and the palladium-catalyzed decarboxylative cycloaddition reactions are powerful synthetic tools. Vinyl benzoxazinones have emerged as versatile building blocks for nitrogenous skeletons.
Article
Biochemistry & Molecular Biology
Ramil F. Fatykhov, Igor A. Khalymbadzha, Ainur D. Sharapov, Anastasia P. Potapova, Nataliya N. Mochulskaya, Anton N. Tsmokalyuk, Alexandra Ivoilova, Polina N. Mozharovskaia, Sougata Santra, Oleg N. Chupakhin
Summary: A different type of MnO2-induced oxidative cyclization of dihydrotriazines has been developed, providing facile access to naphthofuro-fused triazine via C-C/C-O oxidative coupling reaction. The scalability of the reaction has been demonstrated, and further application of the synthesized compound has been showcased.
Article
Chemistry, Organic
Chada Raji Reddy, Ejjirotu Srinivasu, Muppidi Subbarao
Summary: In this study, we present the first example of ipso-carbocyclization of N-propiolyl-2-arylbenzimidazoles, which involves both radical-based and electrophilic reactions, leading to the synthesis of a wide range of chalcogenated benzimidazo-fused azaspiro-[5,5]-undecatrienones in good yields.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Wangyu Shi, Yue Ren, Haoran Zhao, Yi Tang, Shixiang Piao, Biming Mao, Wei Wang, Yongjun Wu, Bo Wang, Hongchao Guo
Summary: A phosphine-catalyzed reaction successfully synthesized new polycyclic compounds, which were further reacted with specific reagents to obtain substituted products with high yields.
Article
Chemistry, Organic
Marina Yu. Dvorko, Dmitrii A. Shabalin, Igor A. Ushakov, Elena Yu. Schmidt, Boris A. Trofimov
Summary: The cascade dimerization of alkynones with sterically hindered secondary alkyl groups at the carbonyl function unexpectedly produced highly functionalized furans. This reaction efficiently takes place at room temperature in the presence of a potassium tert-butoxide/dimethylsulfoxide superbase catalytic system. Alkynones with an additional C-H active site at the carbon-carbon triple bond followed a different dimerization pathway to form 3-alkenylpyran-4-ones. The discovery of these reactions expands the traditional understanding of alkynone reactivity in strong basic conditions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Hui Xu, Ming-Jun Li, Hong Chen, Fei-Hong Huang, Qi-Yue Zhu, Guan-Wu Wang, Ze Zhang
Summary: A novel and efficient multi-component reaction has been developed for the synthesis of polysubstituted pyrroles. This protocol offers several advantages including mild reaction conditions, broad substrate scope, and high efficiency.
Article
Chemistry, Organic
Yan He, Qimeng Liu, Jintao Yang, Zhi Zheng, Guo-Li Chai, Xinying Zhang, Xuesen Fan
Summary: In this study, a convenient method for functionalizing multiple C(sp3)-H bonds of saturated cyclic amines was described. The method involves oxidation with oxoammonium salt to produce a fi-oxo cyclic iminium ion, which then undergoes cascade addition with thiocyanate and various N-, O-, and S-containing nucleophiles in green solvent and ethanol. Notably, chiral spiro azapolyheterocycles were successfully synthesized with high enantioselectivity when cysteine or serine esters were used as substrates. This method was also applied for concise late-stage modification of several natural product derivatives.
Article
Chemistry, Organic
Toktam S. Shirazian, Hossein Zahedian Tejeneki, Ali Nikbakht, Frank Rominger, Saeed Balalaie
Summary: This study presents a novel method for synthesizing functionalized acridines using a base-promoted formal [4+2] cycloaddition reaction. The method exhibits high selectivity and efficiency, making it a valuable approach for the synthesis of acridine backbones.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Vikram Singh, Bal Krishna Mishra, Deepak Kumar, Bhoopendra Tiwari
Summary: In this study, we have demonstrated a novel method for the construction of C4-heterofunctionalized pyrazolines by introducing heteroatoms onto the ring. This method has important applications for the synthesis of oxyacylated and aminated products with multiple stereocenters.
