Article
Chemistry, Organic
Lijie Zhang, Ling Fang, Hao Huang, Chaofan Wang, Fang Gao, Zhiyong Wang
Summary: The study presents a novel and reliable method for synthesizing biologically interesting benzo[e][1,4]thiazepine derivatives in synthetically useful yields. Postsynthetic modification also leads to the formation of its sulfoxide and sulfone derivatives.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Physical
Mercedes Zurro, Aitor Maestro
Summary: This paper reviews the recent literature on the catalytic methodologies for the derivatization of aza-QM, including organocatalytic and organometallic approaches. The review analyzes various catalytic systems, involving chiral NHC carbenes, phosphoric acids, phosphoramidites, phosphine, copper, and palladium catalysis, showcasing their applicability for the synthesis of a diverse array of N-containing compounds, many of which exhibit biological activity.
Article
Chemistry, Multidisciplinary
Pei-Shan Wu, Yan-Cheng Liou, Gangababu Marri, Yi-Ru Chen, Jia-Rong Wu, Wenwei Lin
Summary: An efficient synthesis of chromeno[4,3-b]pyrrolidines has been developed via a mild base-catalyzed reaction, achieving excellent diastereoselectivity.
JOURNAL OF THE CHINESE CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Suo-Suo Qi, Hao Yin, Yi-Feng Wang, Chao-Jie Wang, Hong-Te Han, Tong-Tong Man, Dan-Qian Xu
Summary: A new method has been developed for the selective construction of enantioenriched eight-membered cyclic ethers by combining squaramide and DBU catalysis. The reaction yields a variety of eight-membered cyclic ethers with high stereoselectivity, showcasing the practicality of ynones as C4-syntons for synthesizing chiral medium-membered rings.
Article
Chemistry, Organic
Ganesh Shivayogappa Sorabad, Ding-Yah Yang
Summary: A facile and regioselective Lewis acid-catalyzed cascade annulation of o-hydroxyphenyl propargyl amines with 4-hydroxycoumarin to afford furano[3,2-c]coumarin and pyrano[3,2-c]coumarin derivatives is reported. The reaction proceeds through the conjugate addition of 4-hydroxycoumarin to the in situ-generated alkynyl o-quinone methide followed by intramolecular 5-exo-dig and 6-endo-dig annulation to form furano[3,2-c]coumarins and pyrano[3,2-c]coumarins, respectively. The prepared o-hydroxyl substituted pyrano[3,2-c]coumarins can be easily transformed into the corresponding coumarin-derived dioxabicycles by acid-mediated cyclization.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Haruna Araki, Shohei Furuya, Kazuya Kanemoto, Shin-ichi Fukuzawa
Summary: The conjugated addition reaction of 1-pyrroline-5-carbonitrile to alpha-enones was effectively catalyzed by AgF/ThioClickFerrophos (TCF) in diethyl ether in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), and nearly single diastereomers of adducts with good enantiomeric excesses (up to 97% ee) were obtained in high yields. The reduction of the nitrile group with H2/Raney Ni in ethanol successfully transformed the conjugate adduct to the corresponding spirocyclic piperidine (60% yield) as a single stereoisomer.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Jing Zhang, Yi-Fei Li, Feng-Cheng Jia, Yang Gao, Xiao-Qiang Hu
Summary: This study successfully achieves the first [3 + 2] annulation of readily available 3-aminooxetanes and 1,3,5-triazinanes. The reaction conditions are mild and operation is simple, leading to the synthesis of a range of structurally diverse 4-hydroxymethyl imidazolidines.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Lu Lei, Yu-Feng Liang, Cui Liang, Jiang-Ke Qin, Cheng-Xue Pan, Gui-Fa Su, Dong-Liang Mo
Summary: A variety of tetrahydroquinoline-fused bicycles with multiple stereocenters are synthesized in good yields with high diastereoselectivity through Cu2O-catalyzed [4 + 2] cycloaddition. Mechanistic studies show that the Cu(i) catalyst facilitates the formation of ao-QMs through a radical process and accelerates the [4 + 2] cycloaddition. The reaction can be easily scaled up and the products obtained can be converted into diverse tetrahydroquinoline scaffolds.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Applied
Navpreet Kaur, Priyanka Singh, Prabal Banerjee
Summary: An efficient protocol for the synthesis of spiro-imidazolidinone-cyclohexadienones from p-quinone methides and dialkyloxy ureas is reported, showing good functional group tolerance and providing a straightforward method for accessing the desired compounds. Additionally, the debenzylation of spiroimidazolidinones to give N-hydroxycyclic ureas has been demonstrated in follow-up chemistry.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Inorganic & Nuclear
Anand Pariyar, Debesh Sharma, Sagarmani Rasaily, Shivanand Chettri, Disha Sureka, Sudarsan Tamang
Summary: This study reports the synthesis of a novel 2D metal-organic framework with pre-existing unsaturated Lewis acid sites, which can be directly used for catalyzing organic transformations and synthesizing biologically active chiral imidazolidines. The material exhibits excellent reusability and high stereoselectivity.
INORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Mamta Gill, Arko Das, Vinod K. Singh
Summary: An enantioselective (3+2) cycloaddition reaction has been reported for the synthesis of chiral polysubstituted pyrrolidines. The reaction displays opposite regioselectivity with excellent enantioselectivities and yields. Interestingly, changing the alpha-substituents of the iminoesters results in the formation of normal (3+2) cycloaddition products with excellent enantioselectivities as well.
Article
Chemistry, Organic
Jose Cortes Vazquez, Jacqkis Davis, Vladimir N. Nesterov, Hong Wang, Weiwei Luo
Summary: A formal [3 + 3] cyclization reaction has been developed for the synthesis of 1,3,4-oxadiazinanes with generally high yields (up to 96%). The reaction, catalyzed by Sc(OTf)(3), has a broad substrate scope for both diaziridines and quinones. The synergistic activation of 1,3-dipolar diaziridines and dipolar quinones was found to be essential for enabling this reaction.
Article
Chemistry, Organic
Xuemei Wang, Liang Zhou, Hongkui Zhang, Xiaoyu Ren, Guowei Gao, Tianli Wang
Summary: A highly enantioselective cascade reaction of beta,gamma-unsaturated carbonyl compounds using bifunctional ion-pair catalysis has been developed, resulting in functionalized chiral 1,3-dioxolochroman derivatives with high yields and excellent stereoselectivities. The utility of this method was demonstrated through one-pot synthesis, scaled-up preparation, and facile transformation. Mechanistic investigations provided insights into the reaction pathway and chiral induction.
Article
Chemistry, Organic
Rupashri Dash, Sudhir Kumar Hota, Sandip Murarka
Summary: We describe an efficient higher order conjugate addition reaction of azauracils to substituted para-quinone methides (p-QMs) mediated by triethylamine, forming previously unknown diarylmethane scaffolds through C-N bond formation. This protocol offers mild conditions, high atom economy, broad scope, and allows convenient access to biologically relevant new chemical entities (NCEs) consisting of p-QM and azauracil hybrids in good to excellent yields.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Multidisciplinary
Shuang-Jing Zhou, Xiao Cheng, Chun-Xia Hu, Guo-Yong Xu, Wen-Jing Xiao, Jun Xuan
Summary: A formal [4+3]-cycloaddition reaction between ortho-hydroxyphenyl-substituted para-quinone methides and in-situ generated azaoxyallyl cations is reported here. This reaction provides a very efficient route to a series of biologically important 1,4-benzoxazepine derivatives in good to excellent yields under mild reaction conditions.
SCIENCE CHINA-CHEMISTRY
(2021)
