Article
Chemistry, Multidisciplinary
Jie Liu, Gregor S. Cremosnik, Felix Otte, Axel Pahl, Sonja Sievers, Carsten Strohmann, Herbert Waldmann
Summary: This study presents the design and synthesis of a collection of 155 pyrroquinoline pseudo-NPs, combining fragments characteristic of tetrahydroquinoline and pyrrolidine classes in novel arrangements. Cheminformatic analysis and biological evaluation revealed chemically diverse pseudo-NP classes with distinct bioactivity patterns, dependent on fragment connectivity and regioisomeric arrangement.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Yao Xu, Hai-Xiang Gao, Chengkai Pan, Yue Shi, Chi Zhang, Genping Huang, Chao Feng
Summary: By using photoredox catalysis, we have achieved the (3+3) dipolar cycloaddition of nitrones with aryl cyclopropanes. This reaction exhibits excellent regio- and stereoselectivity and can be applied to a variety of aryl cyclopropane substrates.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Organic
Zivota Selakovic, Andrea M. Nikolic, Vladimir Ajdacic, Igor M. Opsenica
Summary: Decarbonylation is a valuable reaction used in various life forms and laboratories, primarily catalyzed by transition metals such as Wilkinson's catalyst. It has applications in the synthesis of natural products and their derivatives, with potential advantages and disadvantages to consider for future research.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Olga O. Sokolova, John F. Bower
Summary: An enantioselective (3+1+2) cycloaddition reaction triggered by carbonylative C-C bond activation of cyclopropanes is achieved using an endo-directing group strategy. This reaction represents a rare example where C-C bond oxidative addition determines the enantiomeric outcome, and it is the first time this has been achieved within the context of a multicomponent reaction design.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Ming Bao, Karlos Lopez, Raj Gurung, Hadi Arman, Michael P. Doyle
Summary: A highly enantioselective synthesis of chiral dihydro-3H-carbazole-2-carboxylate derivatives is achieved via a one-pot cascade reaction catalyzed by nickel(II) perchlorate hexahydrate and scandium(III) trifluoromethanesulfonate. The reaction proceeds under mild conditions and provides the desired products in high yields and enantioretention. Furthermore, these dihydro-3H-carbazole-2-carboxylates can be transformed into decarboxylated compounds through hydrolysis and decarboxylation under unexpectedly mild reaction conditions, giving moderate yields with high retention of enantiomeric purity.
Article
Chemistry, Physical
Ming Bao, Karlos Lopez, Raj Gurung, Hadi Arman, Michael P. Doyle
Summary: A highly enantioselective synthesis of chiral dihydro-3H-carbazole-2-carboxylate derivatives is achieved via a one-pot cyclopentannulation-rearrangement cascade reaction. The reaction is catalyzed by nickel(II) perchlorate hexahydrate and scandium(III) trifluoromethanesulfonate, and involves the use of 3-methylindole and non-racemic donor-acceptor cyclopropanes. The resulting products show high yields and enantioretention under mild reaction conditions, and further transformation into decarboxylated compounds can be achieved with moderate yields and high enantiomeric purity.
Article
Chemistry, Multidisciplinary
Zhan-Yu Zhou, Zhong-Yang Xu, Qiao-Yu Shen, Li-Sha Huang, Xing Zhang, Ai-Bao Xia, Dan-Qian Xu, Zhen-Yuan Xu
Summary: A new and efficient strategy has been developed for the divergent synthesis of enynes and enesters through ring-opening reactions of nitrocyclopropanes. The approach resulted in high yields of up to 89% and 90% for enynes and enesters, respectively. The reaction is characterized by its easy operation, use of green solvents and simple inorganic bases, and being transition-metal free.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Jade McDaniel, Christopher A. Farley, Antonio Ramirez, Bhupinder Sandhu, Amy Sarjeant, Qing Shi, Arthur Han, William P. Gallagher, John Hynes, T. G. Murali Dhar, Francisco Gonzalez-Bobes, John R. Coombs, David Marcoux
Summary: The use of novel annulating reagents allows for the diastereoselective synthesis of carbocycles with multiple stereocenters, providing excellent stereochemical control and enabling the synthesis of pharmacologically relevant compounds with high enantioselectivity and yield.
Article
Chemistry, Multidisciplinary
Nils L. Ahlburg, Oliver Hergert, Peter G. Jones, Daniel B. Werz
Summary: A novel class of highly activated donor-acceptor cyclopropanes with a single vinylogous acceptor is presented. These moieties undergo cycloaddition reactions with various substrates to form carbo- and heterocycles. The stereochemical outcome can be controlled by the choice of catalyst. Mechanistic and kinetic experiments were conducted to explain the catalytic cycle and stereoselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Muhammad Fahad Jamali, Usha Yadav, Mary Merlin Manjaly Babu, Ruchir Kant, Kishor Mohanan
Summary: Here, we report the generation of a cyanonitrone in situ from diazoacetonitrile and nitrosoarene, and its subsequent [3+2] cycloaddition with oxabicyclic alkenes to form fused tricyclic cyanoisoxazolidines. This method can also be applied to access fused tricyclic trifluoromethylated and phosphonylated isoxazolidines. Interestingly, the reductive ring-opening of cyanoisoxazolidines followed by a spontaneous lactonization produces fused tricyclic amino lactones. Additionally, the N-O bond of the obtained tricyclic trifluoromethylated isoxazolidines can be cleaved to obtain 1,3-amino alcohols.
CHEMICAL COMMUNICATIONS
(2023)
Review
Chemistry, Organic
Hoang-Minh To, Oleksii Malets, Maryna Mazur, Olha Mykhailenko, Olena Kompaniiets, Thierry Ollevier
Summary: Halodiazirines, as important reagents, have been widely applied in photochemical and thermal cyclopropanation reactions. This article reviews the synthetic applications of Halodiazirines as halocarbene precursors in various reactions with alkenes.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Prasoon Raj Singh, Pratibha Kalaramna, Shamsad Ali, Avijit Goswami
Summary: A simple protocol has been developed to access thio-/selenopyrrolines through a (3+2)-cycloaddition reaction using SnCl4 as a Lewis acid catalyst. Good chemoselectivity was observed when DACs were treated, indicating that thiocyanate is more reactive than nitrile moiety in such reactions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Pharmacology & Pharmacy
Luis D. Gonzalez-Morales, Adriana Moreno-Rodriguez, Lenci K. Vazquez-Jimenez, Timoteo Delgado-Maldonado, Alfredo Juarez-Saldivar, Eyra Ortiz-Perez, Alma D. Paz-Gonzalez, Edgar E. Lara-Ramirez, Lilian Yepez-Mulia, Patricia Meza, Gildardo Rivera
Summary: Cutaneous leishmaniasis (CL) is a global public health problem without available vaccines and with limited effective treatments. This study performed virtual screening of natural products against Leishmania mexicana using molecular docking, and selected four compounds with promising leishmanicidal activity. The ADME-Tox analysis suggested favorable properties for these compounds, and one of them, S-8, exhibited higher activity than the reference drug glucantime.
Article
Biochemistry & Molecular Biology
Cetin Bayrak, Parham Taslimi, Namik Kilinc, Ilhami Gulcin, Abdullah Menzek
Summary: In this study, the natural bromophenol butyl 2-(3,5-dibromo-4-hydroxyphenyl)acetate (1) and indene derivatives 34 and 35 were successfully synthesized. Several known natural bromophenols and their derivatives were also synthesized. The synthesized compounds exhibited strong inhibition effects against acetylcholinesterase, butyrylcholinesterase, and α-glycosidase enzymes.
CHEMISTRY & BIODIVERSITY
(2023)
Article
Chemistry, Organic
Prasoon Raj Singh, Braj Gopal, Madan Kumar, Avijit Goswami
Summary: A metal/additive-free method for the synthesis of propargylic cyclic imine derivatives has been established. The reaction involves a (3 + 2)-cycloaddition of donor-acceptor cyclopropanes and alkynylnitriles in the presence of BF3 center dot OEt2. The method provides access to a variety of propargylic cyclic imine derivatives in good to excellent yields, and the synthesis of propargylic amines and stable enol derivatives from the title compound is also explored.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)