Article
Chemistry, Organic
Jia Seo, Che-Wei Chen, Woohyeong Lee, Ju Eun Jeon, Pei-Ling Chen, Shih-Ching Chuang, Jung Min Joo
Summary: A benzannulation strategy was developed involving activation of two C-H bonds of five-membered heteroarenes, resulting in fluorescent benzofuran and indole derivatives through Pd-catalyzed oxidative reactions. This strategy provides a potential pathway for further development of functionalized polycyclic heteroaromatic compounds.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Multidisciplinary
Xueting Zhou, Qingqin Huang, Jiami Guo, Lei Dai, Yixin Lu
Summary: A new molecular editing method called skeletal recasting strategy is developed to synthesize fully substituted pyrroles from simple pyrroles through dearomative deconstruction and rearomative reconstruction steps, leading to the synthesis of challenging tetra-substituted pyrroles and anticancer drug Sutent.
ACS CENTRAL SCIENCE
(2023)
Article
Chemistry, Organic
Yoon Sung Cho, Seung Tae Kim, Do Hyun Ryu
Summary: A chiral Lewis acid-catalyzed enantioselective Friedel-Crafts alkylation using in situ-generated o-quinone methides has been developed. The reaction showed high yield (up to 99%) and excellent enantioselectivity (up to >99% ee) in the presence of a chiral oxazaborolidinium ion catalyst.
Article
Chemistry, Multidisciplinary
Fernanda Liu, Lakshita Anand, Michal Szostak
Summary: Skeletal editing through single-atom insertion reactions involving nitrogen heterocycles has been reported, utilizing electrophilic carbonyl cation equivalents and in situ generated nitrenes. This methodology enables transformation of pyrroles and indoles to pyridines, quinolines, and quinazolines, offering an innovative approach to complex molecular structures by heterocycle diversification and peripheral editing. Considering the significance of heterocycles in medicinal chemistry, biology, and natural products, these methods provide a valuable tool for molecular editing.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Review
Chemistry, Organic
Caroline Dorsch, Christoph Schneider
Summary: This review summarizes recent developments in the area of enantioselective cycloadditions catalyzed by Bronsted acids. Through a straightforward transformation, complex polycyclic heterocyclic compounds can be obtained with high yields and excellent stereocontrol. The enantioselectivity of the reaction is controlled by chiral Bronsted acids.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Hai-Tao Yang, Su-Qing Zhou, Dan-Mei Chen, Zi-Jun Hu, Xiao-Qi Qiang, Xiao-Qing Song, Sheng Tan, Wei-Hua Jiang, Yong-Qiang Sun, Chun-Bao Miao
Summary: A copper-catalyzed annulation of O-acyl oximes with cyclic 1,3-diones has been developed, providing a concise synthesis of 7,8-dihydroindolizin-5(6H)-ones and cyclohexanone-fused furans through substituent-controlled selective radical coupling. 2-Alkyl cyclic 1,3-diones undergo C-C radical coupling, while 2-unsubstituted cyclic 1,3-diones undergo C-O radical coupling.
Article
Chemistry, Multidisciplinary
Zhe Meng, Jun Yan, Chao Ning, Min Shi, Yin Wei
Summary: This paper presents an efficient synthetic strategy for the rapid construction of multisubstituted pyrroles, furans, and thiophenes via NXS mediated desulfonylative/dehydrogenative cyclization of vinylidenecyclopropanes. The method offers advantages such as a wide substrate range, high efficiency, and synthetic usefulness of the heterocyclic products under metal-free and mild conditions. The derivatization of pyrrole products and the preparation of functional molecules demonstrate the synthetic potential of the products as platform molecules. The reaction mechanism has been investigated through control experiments and DFT calculations.
Article
Chemistry, Organic
Shu Kai Chen, Ming-Tsung Hsu, Yi-Hung Liu, Shiuh-Tzung Liu
Summary: This study describes a novel method for preparing tetrahydropentaleno[1,2-c]pyrroles (8) through the reaction of anilines with 1-en-4-yn-3-ols in the presence of Lewis acid. The oxidation of 8 using Br2 resulted in the formation of pentaleno[1,2-c]pyrroles (10), representing the first tricyclic 5/5/5 ring with a fully conjugated system. The structures of the obtained compounds were characterized using spectroscopic methods, with compounds 8a,b and 10c further confirmed by X-ray crystallography.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Giovanni Centonze, Chiara Portolani, Paolo Righi, Giorgio Bencivenni
Summary: Axially chiral compounds, once viewed as merely a laboratory curiosity, have gained recognition in the past two decades for their significant role in medicinal, biological, and material chemistry. The asymmetric synthesis of atropisomers, particularly N-N atropisomers, has become a rapidly expanding field with new challenges and frontiers. This review highlights recent advances and breakthroughs in the enantioselective synthesis of N-N atropisomers, showcasing the strategies and frameworks involved.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Anton A. Merkushev, Anton S. Makarov, Pavel M. Shpuntov, Vladimir T. Abaev, Igor V. Trushkov, Maxim G. Uchuskin
Summary: 2-(2-Acylvinyl)indoles obtained by oxidative rearrangement of substituted 2-(2-aminobenzyl)furans can be used to construct structural analogues of antifungal alkaloids caulindoles A-D and other indole-derived molecules and substituted carbazoles by introducing new reaction centers or manipulating functional groups of the obtained compounds.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
D. Magoo, Komal Aggarwal, Shruti Gupta, Kalawati Meena
Summary: A diverse library of nitrogen containing heterocyclic compounds can be synthesized through the versatility of enamine intermediates and multicomponent reactions.
Article
Chemistry, Organic
Ferdinand Taenzler, Jiasu Xu, Sudhakar Athe, Viresh H. Rawal
Summary: This article presents the dearomative (4 + 3) cycloaddition reactions of 3-alkenylindoles with in situ-generated oxyallyl cations, as well as the transformation of the resulting cycloadducts and preliminary investigations into their enantioselective catalysis using imidodiphosphorimidate catalysts.
Article
Engineering, Chemical
Sueli Rodrigues, Fabiano A. N. Fernandes
Summary: This study evaluated the changes that can be made to ready-to-drink coffee by applying cold plasma technology, which can modulate its aroma chemically. The technology increased the significance of desirable descriptors such as nutty, fruity, and green, allowing for the production of specialty or gourmet ready-to-drink coffees.
Article
Chemistry, Organic
Yaling Huang, Zisong Qi, Xingwei Li
Summary: This study presents a rhodium-catalyzed highly enantioselective reaction, which enables the access to functionalized indoles with excellent enantioselectivities through the nucleophilic cyclization of 2-alkynylanilines.
Article
Chemistry, Multidisciplinary
Hui Qiao, Jean Michalland, Qi Huang, Samir Z. Zard
Summary: This study presents a modular approach to highly functional acyl (MIDA)boronates. The radical derived from acetyl (MIDA)boronate is generated and captured by various alkenes, providing access to numerous otherwise inaccessible structures. The reactivity of the acetyl (MIDA)boronate radical allows the synthesis of a wide range of acyl (MIDA)boronates, which can be further transformed into B(MIDA) substituted furans and pyrroles.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Tracy M. M. Maiden, Stephen Swanson, Panayiotis A. Procopiou, Joseph P. A. Harrity
CHEMISTRY-A EUROPEAN JOURNAL
(2015)
Article
Chemistry, Organic
Steven J. Edeson, Elvis J. M. Maduli, Stephen Swanson, Panayiotis A. Procopiou, Joseph P. A. Harrity
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Medicinal
Panayiotis A. Procopiou, Rachael A. Ancliff, Paul M. Gore, Ashley P. Hancock, Simon T. Hodgson, Duncan S. Holmes, Steven P. Keeling, Brian E. Looker, Nigel A. Parr, James E. Rowedder, Robert J. Slack
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2016)
Article
Chemistry, Medicinal
Lena Shukla, Laura A. Ajram, Malcolm Begg, Brian Evans, Rebecca H. Graves, Simon T. Hodgson, Sean M. Lynn, Afjal H. Miah, Jonathan M. Percy, Panayiotis A. Procopiou, Stephen A. Richards, Robert J. Slack
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2016)
Article
Chemistry, Organic
Tracy M. M. Maiden, Stephen Swanson, Panayiotis A. Procopiou, Joseph P. A. Harrity
JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Niall A. Anderson, Ian B. Campbell, Brendan J. Fallon, Sean M. Lynn, Simon J. F. Macdonald, John M. Pritchard, Panayiotis A. Procopiou, Steven L. Sollis, Lee R. Thorp
ORGANIC & BIOMOLECULAR CHEMISTRY
(2016)
Article
Chemistry, Organic
Ben S. Pilgrim, Alice E. Gatland, Carlos H. A. Esteves, Charlie T. McTernan, Geraint R. Jones, Matthew R. Tatton, Panayiotis A. Procopiou, Timothy J. Donohoe
ORGANIC & BIOMOLECULAR CHEMISTRY
(2016)
Article
Chemistry, Organic
Tracy M. M. Maiden, Stephen Swanson, Panayiotis A. Procopiou, Joseph P. A. Harrity
Article
Chemistry, Inorganic & Nuclear
Panayiotis A. Procopiou, Richard J. D. Hatley, Sean M. Lynn, Royston C. B. Copley, Yanan He, Douglas J. Minick
TETRAHEDRON-ASYMMETRY
(2016)
Article
Chemistry, Inorganic & Nuclear
Panayiotis A. Procopiou, Tim N. Barrett, Royston C. B. Copley, Christopher J. Tame
TETRAHEDRON-ASYMMETRY
(2017)
Article
Chemistry, Medicinal
Panayiotis A. Procopiou, Alison J. Ford, Paul M. Gore, Brian E. Looker, Simon T. Hodgson, Duncan S. Holmes, Sadie Vile, Kenneth L. Clark, Ken A. Saunders, Robert J. Slack, James E. Rowedder, Clarissa J. Watts
ACS MEDICINAL CHEMISTRY LETTERS
(2017)
Article
Chemistry, Medicinal
Panayiotis A. Procopiou, Victoria J. Barrett, Keith Biggadike, Peter R. Butchers, Andrew Craven, Alison J. Ford, Stephen B. Guntrip, Duncan S. Holmes, Sara C. Hughes, Anne E. Jones, Brian E. Looker, Peter J. Mutch, Mark Ruston, Deborah Needham, Claire E. Smith
JOURNAL OF MEDICINAL CHEMISTRY
(2014)
Article
Chemistry, Organic
Afjal H. Miah, Royston C. B. Copley, Daniel O'Flynn, Jonathan M. Percy, Panayiotis A. Procopiou
ORGANIC & BIOMOLECULAR CHEMISTRY
(2014)
Article
Chemistry, Organic
Elvis J. M. Maduli, Steven J. Edeson, Stephen Swanson, Panayiotis A. Procopiou, Joseph P. A. Harrity
Article
Biochemistry & Molecular Biology
Afjal H. Miah, Aurelie C. Champigny, Rebecca H. Graves, Simon T. Hodgson, Jonathan M. Percy, Panayiotis A. Procopiou
BIOORGANIC & MEDICINAL CHEMISTRY
(2017)