A synthetic strategy to fused bicyclic piperidines-building blocks for medicinal chemistry-is developed. The key step was an intramolecular [2 + 2]-photocyclization. The photochemical step was performed on a gram scale. Crystallographic analysis of the obtained compounds revealed that they occupy a novel chemical space and can be considered as elongated analogues of 3-substituted piperidines.
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http://dx.doi.org/10.1021/acs.joc.0c02355 | DOI Listing |
Pest Manag Sci
September 2024
Research & Development, PI Industries Ltd., Udaisagar Road, Madri Industrial Area, Udaipur, India.
Background: As an investigative program around the development of novel oomycetes fungicides, a systematic exploration of piperidinyl thiazole fungicides employing a bioisosteric replacement strategy was planned.
Results: A series of novel piperidinyl thiazole analogues were designed, synthesised, and evaluated as fungicides in vitro and in vivo against three oomycete fungal pathogens: Phytophthora infestans (P. infestans), Plasmopara viticola (P.
J Am Chem Soc
July 2024
Department of Medicinal Chemistry, Key Laboratory of Chemical Biology (Ministry of Education), NMPA Key Laboratory for Technology Research and Evaluation of Drug Products, School of Pharmaceutical Sciences, Cheeloo College of Medicine, Shandong University, Jinan, Shandong 250012, China.
The direct construction of bioisosteric compounds enriched in C content represents an attractive and dependable approach to imbuing biologically active molecules with enhanced three-dimensional characteristics, finding wide utility across the synthetic and medicinal chemistry community. Despite recent advancements in the synthesis of (aza)-bicyclo[3.1.
View Article and Find Full Text PDFScience
February 2024
RWTH Aachen University, Institute of Organic Chemistry, Landoltweg 1, D-52074 Aachen, Germany.
The Pauson-Khand reaction has in the past 50 years become one of the most common cycloaddition reactions in chemistry. Coupling two unsaturated bonds with carbon monoxide, the transformation remains limited to CO as a C building block. Herein we report analogous cycloaddition reactions with nitrenes as an N unit.
View Article and Find Full Text PDFChemistryOpen
June 2024
Institute of Organic Chemistry, Justus Liebig University Giessen, Heinrich-Buff-Ring 17, 35392, Giessen, Germany.
In previous works, we demonstrated that tertiary 3-chloropiperidines are potent chemotherapeutics, alkylating the DNA through the formation of bicyclic aziridinium ions. Herein, we report the synthesis of novel secondary 3-chloropiperidine analogues. The synthesis incorporates a new procedure to monochlorinate unsaturated primary amines utilizing N-chlorosuccinimide, while carefully monitoring the temperature to prevent dichlorination.
View Article and Find Full Text PDFJ Am Chem Soc
December 2023
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52056 Aachen, Germany.
Bicyclic amines are important motifs for the preparation of bioactive materials. These species have well-defined exit vectors that enable accurate disposition of substituents toward specific areas of chemical space. Of all possible skeletons, the 2-azabicyclo[3.
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