With the implementation of combinatorial chemistry into the modern drug discovery process, the approach to novel diverse heterocycle libraries is an indispensable requirement. Triazenes, which are concealed diazonium salts, can be used to link functionalized arenes and amines to generate various heterocyclic structures, namely, benzoannelated nitrogen heterocycles, upon cleavage from the resin. Since triazene anchors are stable toward various reagents and perform well under a range of reaction conditions, these multifunctional linkers are well suited for automated solid-phase syntheses and the syntheses of complex organic molecules, such as natural products, on solid supports.
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http://dx.doi.org/10.1021/ar0200145 | DOI Listing |
Org Biomol Chem
January 2025
Catalysis Laboratory, School of Chemistry, University of Hyderabad, Hyderabad-500 046, India.
Benzothiazole and benzoxazole heterocyclic ring-containing 1,4,5-trisubstituted-1,2,3-triazoles are well known for their wide range of applications in pharmaceutical and medicinal chemistry, but their high-yielding metal-free selective synthesis has always remained challenging as no comprehensive simple protocol has been outlined to date. Owing to their structural and medicinal importance, herein, we synthesized various benzothiazole and benzoxazole heterocyclic ring-containing 1,4,5-trisubstituted-1,2,3-triazoles in high to excellent yields with chemo-/regioselectivity from the library of benzothiazole/benzoxazole-ketones and aryl/alkyl-azides through an enolate-mediated organocatalytic azide-ketone [3 + 2]-cycloaddition under ambient conditions in a few hours. The commercial availability or quick synthesis of the starting materials and catalysts, a diverse substrate scope, chemo-/regioselectivity, quick synthesis of pharmaceutically active known compounds and their analogues, and numerous medicinal applications of functionalized benzothiazole/benzoxazole-triazoles are the key attractions of this metal-free organo-click reaction.
View Article and Find Full Text PDFAcc Chem Res
January 2025
Department of Chemistry, University of Wisconsin, 1101 University Avenue, Madison, Wisconsin 53706, United States.
ConspectusThe manipulation of strained rings is a powerful strategy for accessing the valuable chemical frameworks present in natural products and active pharmaceutical ingredients. Aziridines, the smallest N-containing heterocycles, have long served as building blocks for constructing more complex amine-containing scaffolds. Traditionally, the reactivity of typical aziridines has been focused on ring-opening by nucleophiles or the formation of 1,3-dipoles.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
Chemical Sciences Division, Indian Institute of Petroleum, Dehradun, 248005, India.
Retraction of 'Thiourea dioxide promoted efficient organocatalytic one-pot synthesis of a library of novel heterocyclic compounds' by Sanny Verma , , 2011, , 6943-6948, https://doi.org/10.1039/C1OB05818E.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, Innovative Drug Research Center, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331, China.
Synthesis of chemically diverse heterocyclic scaffolds in DNA-encoded libraries is highly demanded. We herein reported a convenient one-pot multi-component on-DNA synthetic strategy to afford multi-substituted 2,3-dihydrofuran scaffolds pyridinium ylide-mediated cyclization. This reaction exhibited modest to excellent conversions for a broad range of DNA-conjugated aldehydes, β-ketonitriles and pyridinium salts under mild reaction conditions.
View Article and Find Full Text PDFCurr Med Chem
January 2025
Laboratory of Analytical and Molecular Chemistry, Faculty of Sciences Ben M'Sik, Hassan II University of Casablanca, Sidi Othman, Box 7955, Casablanca, Morocco.
Alzheimer's disease (AD) is a chronic and progressive neurodegenerative brain disorder, primarily affecting the elderly. Its socio-economic impact and mortality rate are alarming, necessitating innovative approaches to drug discovery. Unlike single-target diseases, Alzheimer's multifactorial nature makes single-target approaches less effective.
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