Article
Chemistry, Applied
Santosh J. Gharpure, Santosh K. Nanda, Dipak J. Fartade
Summary: This study demonstrates a facile synthesis of 1,4-heterocycle-fused quinoline motifs through intramolecular formal [4+2]-cycloaddition, involving tandem bond formation reactions and showing excellent functional group tolerance, leading to the synthesis of enantiomerically enriched compounds. Additionally, sulfoxide embedded quinolines were successfully transformed into pentacyclic 1,4-thiepino tethered indeno-quinoline scaffolds via Pummerer cyclization.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Meng-Hao Yi, Hai-Shan Jin, Ru-Bing Wang, Li-Ming Zhao
Summary: An efficient copper-catalyzed cascade annulation of o-hydroxyphenyl propargylamines and pyrazolin-5-ones is described, leading to the rapid assembly of a series of valuable pyrano[2,3-c]pyrazoles with good yields across a wide range of substrates in a simple fashion. The mechanistic elucidation is well supported by control experiment and literature precedents.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Pharmacology & Pharmacy
Huajie Li, Zhenjie Yu, Haoyi Sun, Bo Liu, Xin Wang, Zhe Shao, Meiling Wang, Weilin Xie, Xingang Yao, Qingqiang Yao, Ying Zhi
Summary: A novel reaction between N-(o-chloromethyl)aryl amides and 3-chlorooxindoles has been reported for the synthesis of a series of 2,3'-spirobi(indolin)- 2'-ones in high yields. Compound 3a was found to change mitochondrial morphology and induce mitophagy pathway, potentially triggering mitophagy in cancer cells.
FRONTIERS IN PHARMACOLOGY
(2022)
Review
Chemistry, Multidisciplinary
Maria Tereza M. Martins, Flaviana Rodrigues F. Dias, Raphael Silva M. de Moraes, Marcos Felipe da Silva, Kaio R. Lucio, Karin D'Oliveira Goes, Patrick A. do Nascimento, Andre S. S. da Silva, Vitor F. Ferreira, Anna C. Cunha
Summary: This article provides an overview of multicomponent reactions (MCRs) that involve ortho-quinone methide intermediates (o-QM) and discusses their applications in organic synthesis and biological processes. QMs are generated through eliminative processes or photochemical reactions and can undergo various types of reactions.
Article
Chemistry, Organic
Surya Pratap Singh, Shivani Arora, Anand Singh
Summary: This article describes an efficient method for synthesizing substituted spirochromans and dihydrocoumarins through a three-component reaction involving aromatic aldehydes, phenols, and phenylene dithiolanes. This FeCl3-catalyzed reaction utilizes either aromatic aldehydes or their acetals to generate o-quinone methides in situ, which then undergo a formal [4+2] cyclization with phenylene dithiolanes. Control of temperature allows the direct access to dihydrocoumarins by removing the thioacetal moiety.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Damodar Enagandhula, Raju Adepu, Prathama S. Mainkar
Summary: An efficient and diastereoselective synthesis of 1',4'-dihydro-2'H-spiro[indoline-3,3'-quinolin]-2-one derivatives was achieved using a catalytic amount of L-proline. The tandem reaction involved aza-Michael addition and aldol reaction, and proceeded under mild conditions with a broad substrate scope and excellent diastereoselectivity, providing good to excellent yields.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Multidisciplinary
Bao-Cheng Wang, Li Rao, Kai-Xin Fang, Bao-Le Qu, Fen-Ya Xiong, Ying Feng, Ying Tan, Liang-Qiu Lu, Wen-Jing Xiao
Summary: Metal-polarized aza-ortho-quinone methides (aza-o-QMs) have been effectively utilized in azaheterocycle synthesis, and a new reaction mode involving transient dearomatized spiroaziridine intermediates has been discovered. This has led to the efficient and flexible divergent synthesis of bis-nitrogen heterocycles through sequential dearomatization-rearomatization reactions. Experimental, theoretical, and cellular evaluations have been conducted to explain the mechanisms, selectivity, and potential medicinal applications of the synthesized compounds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Biochemistry & Molecular Biology
Yueteng Zhang, Peng Ji, Xiang Meng, Feng Gao, Fanxun Zeng, Wei Wang
Summary: A simple arylamine-catalyzed Mannich-cyclization cascade reaction was developed for facile synthesis of substituted 2H-benzo[h]chromenes, which involved the efficient generation of ortho-quinone methides (o-QMs) catalyzed by a simple aniline. The mild reaction conditions allowed for a broad spectrum of 1- and 2-naphthols and trans-cinnamaldehydes to engage in the cascade sequence with high efficiency.
Article
Chemistry, Organic
Wen-Kang Wang, Fei-Yun Bao, Si-Tian Wang, Sheng-Yin Zhao
Summary: A method for preparing 3-aminomethylated maleimides via Morita-Baylis-Hillman (MBH) reaction was developed. This study used maleimides and 1,3,5-triazinanes as substrates, and through the phosphine-catalyzed coupling, a series of 3-aminomethylated maleimide derivatives were obtained with a yield of 41-90%. Acylation, isomerization, and Michael addition reactions demonstrated the synthetic application of this method. Control experiments revealed that phosphorus ylide formation and elimination occur during the reaction pathway.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Chuan-Chuan Wang, Xue-Hua Liu, Xin-Lu Wang, Hua-Peng Cui, Zhi-Wei Ma, Degang Ding, Jun-Tao Liu, Lei Meng, Ya-Jing Chen
Summary: A one-step synthesis of functionalized 2,3-unsaturated 4,1-benzothiazepines via [4+3] annulation of aza-o-quinone methides and pyridinium 1,4-zwitterionic thiolates has been developed. The resulting 4,1-benzothiazepines can be easily converted into biologically interesting sulfoxides and sulfones through selective oxidation with m-CPBA under mild and metal-free conditions.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Huaibin Yu, Shuangshuang Wang, Jianjian Huang, Yu Fu, Manfred Wagner, Tanja Weil, Fangrui Zhong, Weining Zhao, Yuzhou Wu
Summary: This article reports the molecular design of a novel multifunctional reagent for light-controlled selective protein labeling. The molecule combines the functionalities of protein-ligand recognition, bioconjugation, ligand cleavage, and photoactivation. By releasing a highly electrophilic o-naphthoquinone methide, the reagent achieves proximity-driven selective labeling with the protein of interest while retaining its native function.
Article
Chemistry, Organic
Chao Xia, Dongchao Wang, Haiming Guo
Summary: Efficient alkylation of purines with ortho-hydroxybenzyl alcohols under mild condition has been achieved by Sc(OTf)(3) catalysis, leading to the formation of various acyclic nucleoside analogs with excellent yields of up to 96% and maintained yields as reactions were scaled up.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Multidisciplinary Sciences
Waldemar Iwanek
Summary: This paper describes the reaction pathways and activation energies of alkoxybenzyl derivatives of resorcin[4]arene leading to the formation of o-quinomethide derivatives of resorcin[4]arene. The reaction mechanisms of o-QMR[4]A formation were proposed based on the calculated pathways. The energies of reactants, transition states, and products were calculated using different density-functional theory methods, and the theoretical reaction mechanisms were discussed in relation to experimental data.
ROYAL SOCIETY OPEN SCIENCE
(2022)
Article
Chemistry, Organic
Yuanyuan Huang, Nan Wang, Zheng-Guang Wu, Xinxing Wu, Mengke Wang, Weichun Huang, You Zi
Summary: The synthesis of alpha-phosphoryloxy carbonyls has been achieved through the sequential in situ formation of a Kukhtin-Ramirez adduct and a P(NMe2)(3)-catalyzed process for the phosphination of alpha-dicarbonyls. Various P(O)-H derivatives, including diarylphosphine oxides, arylphosphinates, and phosphinates, can be introduced into the alpha-dicarbonyls, resulting in the formation of different alpha-phosphoryloxy carbonyls. This method offers advantages of mild conditions, simplicity, atom economy, high efficiency, and gram-scale synthesis, making it a promising tool in synthesis.
Article
Chemistry, Applied
Pei-Hao Dou, Yan Chen, Yong You, Zhen-Hua Wang, Jian-Qiang Zhao, Ming-Qiang Zhou, Wei-Cheng Yuan
Summary: An organocatalyzed asymmetric dearomative [3+2] annulation reaction of electron-deficient 2-nitrobenzo heteroarenes with 3-isothiocyanato oxindoles was developed, providing access to structurally diverse polycyclic spirooxindoles with three contiguous stereogenic centers in high yields with good diastereo- and enantioselectivities. This organocatalysis protocol offers complementary diastereoselectivity compared to previous work with transition metal catalysis.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
