Article
Chemistry, Organic
Jodie L. Hann, Catherine L. Lyall, Gabriele Kociok-Kohn, Simon E. Lewis
Summary: This study presents a method for the synthesis of N-alkoxycarbonyl pyrroles by the condensation of readily available O-substituted carbamates with 2,5-dimethoxytetrahydrofuran. It is demonstrated that N-alkoxycarbonyl protection can impart distinct reactivity to pyrrole in comparison with N-sulfonyl protection.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Penchala Latha, Rajagopal Nagarajan
Summary: A concise synthetic route with good overall yield was developed for the total synthesis of five pyrrolo-azepine containing alkaloids, including aspastipuline and portulacatone, from a commercially available starting material, ethyl 1H-pyrrole-2carboxylate, via a key step of TFAA mediated intramolecular Friedel-Crafts acylation. These alkaloids exhibit significant anticancer properties and moderate antiinflammatory activities.
Article
Chemistry, Organic
Duc Chu, Jonathan A. A. Ellman
Summary: Unprotected, alpha,beta-disubstitutedtryptaminesand phenethylamines can be obtained through a one-pot, metal-free sequence involving in situ formation of aziridinium salts and subsequent Friedel-Crafts reaction with electron-rich (hetero)-arenes. The use of hexafluoroisopropanol as the solvent greatly facilitates both steps. This method is effective for variously substituted indoles and 1,3,5-trimethoxybenzene, as well as cyclic and acyclic alkenes, exhibiting stereospecificity for both (E)- and (Z)-1,2-disubstituted alkenes. Additionally, a diamine can be synthesized via one-pot morpholine addition to an aziridinium salt.
Article
Chemistry, Organic
Song Zou, Zeyu Zhang, Chao Chen, Chanjuan Xi
Summary: The MeOTf-catalyzed intramolecular acyl-cyclization of aryl isocyanates provides (NH)-phenanthridinones and lactams under metal-free conditions, with good to excellent yields and tolerance for a variety of functional groups. The reaction can be scaled up to gram scale and used for the direct or short-step synthesis of natural alkaloids with high yields.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Hassan A. K. Abd El-Aal
Summary: This paper describes an efficient method for accessing tetracyclic pyrazole-fused carbo- and N-heterocyclic systems. The method involves intramolecular Friedel-Crafts cycliacylations of synthesized pyrazole-based carboxylic acid or ester derivatives aided by treatment with Lewis and Bronsted acids. The required starting carbaldehyde was obtained by the Vilsmeier-Haack reaction of the corresponding 2-acetylnaphthalene hydrazone. Our developed strategy, involving a three-step route, offers easy access to tetracyclic pyrazole-fused systems in moderate to good yields.
AUSTRALIAN JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Applied
Haeun Park, Sunwoo Lee
Summary: The Friedel-Crafts acylation reaction was conducted between activated amides and arenes using [Pd(cinnamyl)Cl](2) and Cu(OTf)(2) as catalysts. A variety of N-phenyl-N-tosylbenzamides with substituted phenyl rings underwent reactions with different arenes, including mesitylene, toluene, anisole, 4-tert-butylbenzene, o-xylene, m-xylene, and p-xylene, resulting in the corresponding diaryl ketones with yields ranging from 49% to 89%.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Hejiang Luo, Tongxiang Cao, Shifa Zhu
Summary: The metal-guided method described in the text allows for the divergent synthesis of ketone-fused indoles/pyrroles from N-(2-alkynylaryl) lactam, using regioswitchable Friedel-Crafts cyclization of acylium. The method offers wide substrate scopes, high atom economy, and step economy, making it suitable for the synthesis of structure-related bioactive compounds.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Correction
Chemistry, Multidisciplinary
Latif Ullah, Guoying Zhao, Zichen Xu, Hongyan He, Muhammad Usman, Suojiang Zhang
Summary: A correction is needed for Figure 9 in the publication referenced above.
SCIENCE CHINA-CHEMISTRY
(2021)
Article
Engineering, Environmental
Wen-Hui Hu, Meng-Nan Liu, Qun-Xing Luo, Jianbo Zhang, Huiyong Chen, Long Xu, Ming Sun, Xiaoxun Ma, Qing-Qing Hao
Summary: This study investigates the influence of microscale structure of MWW zeolites on the kinetics for acylation of anisole with acetic anhydride. It is found that the acylation reaction occurs solely on the external acid sites of MWW zeolites, and the single-layer MWW (SL-MWW) exhibits higher recycle stability compared to the multiple-layer MWW (ML-MWW). The confinement effect within 12MR pockets on the surface of SL-MWW results in difficult desorption of product and small rate constant.
CHEMICAL ENGINEERING JOURNAL
(2023)
Article
Chemistry, Organic
Xi Xiao, Xiaobiao Lu, Ming Zhang, Haoqing Hou, Changfeng Wan, Jinbiao Liu
Summary: A novel synthetic method was successfully developed for the preparation of multisubstituted dihydrochromeno[2,3-b]indole derivatives in moderate to high yields using a catalytic environmentally benign iron salt.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Engineering, Environmental
Yehezkiel Steven Kurniawan, Arif Cahyo Imawan, Yoeretisa Miggia Stansyah, Tutik Dwi Wahyuningsih
Summary: A simple and efficient method for synthesizing acetophenone derivatives using PdO-activated bentonite as a heterogeneous catalyst was successfully developed. The synthesis of acetophenone derivatives with various substituents at the para position achieved high yields under optimal conditions. The catalysis mechanism was proposed to be mainly facilitated by the acid sites of the PdO-activated bentonite catalyst, which showed good recyclability and environmental friendliness.
JOURNAL OF ENVIRONMENTAL CHEMICAL ENGINEERING
(2021)
Article
Chemistry, Organic
Yunlong Zhao, Rou Xiao, Weibin Fang, Junling Zhao
Summary: This study presents a protocol for the highly selective addition reaction of isatin-derived beta,gamma-unsaturated alpha-ketoesters with 4-aminoindoles at the C7 position. The reaction, catalyzed by a SPINOL-derived chiral phosphoric acid, yields bisindole derivatives with up to 97% enantiomeric excess. Further biological testing revealed that the products have high cytotoxicity against various cancer cell lines.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Dwaipayan Das, Agniva Das, Saiful Islam, Asish R. R. Das, Adrita Banerjee, Romit Majumder, Debasish Bandyopadhyay
Summary: An efficient and intriguing method using Rh(II) catalysis has been developed for the preparation of fused furan moieties. The technique involves a one-pot C-H activation/concomitant tandem annulation process using an enolic compound and a beta-keto sulfoxonium ylide as reactants. The synthesis only requires Rh-2(TFA)(4) as the catalyst, removing the need for additional metallic or nonmetallic additives. This transformation of naphthoquinone fused furan into highly decorated naphthoquinone fused indolizines shows great promise in synthetic applications.
Article
Chemistry, Organic
Kaikai Wang, Rong Zeng
Summary: This study presents a photoinduced iron catalysis that efficiently cleaves C-C bonds and brominates or iodinates unstrained tertiary cycloalkanols using NBS/NIS. The reaction demonstrates good functional group tolerance and high yields under mild conditions, providing a powerful tool for the synthesis of remote halogenated alkyl ketones. The resulting products can be further converted to valuable molecules through nucleophilic substitution or cross-coupling reactions.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Analytical
Ching-Bin Ke, Ru-Yu Yan, Jian-Lian Chen
Summary: The molecularly imprinted HCP has a mesoporous structure and excellent fluorescence properties. It shows linear fluorescent intensity with TA concentration, and exhibits good selectivity and sensitivity.
