An efficient SAr approach for generating a wide array of 2-aryl and 2-alkyl pyrimidines in good to high yields was developed. This methodology does not require precious metal catalysts and is compatible with aryl, heteroaryl, and alkyl magnesium halides as nucleophiles. This process is scalable and performed at room temperature well below the temperature of the competing decomposition of the activated 2--butyl sulfonyl pyrimidine electrophile.
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http://dx.doi.org/10.1021/acs.orglett.4c01217 | DOI Listing |
Org Lett
October 2024
Department of Organic Chemistry, Bergische Universität Wuppertal, Gaußstraße 20, 42119 Wuppertal, Germany.
We present a novel synthetic approach for the synthesis of the 1,2,3-triazole core, with a particular focus on the direct and regioselective synthesis of the synthetically more challenging triazoles having additional substituents at the N nitrogen atom. Through treatment of readily accessible geminal diazides with organic hydrazines under mild thermolysis conditions, a broad spectrum of -alkyl- and -aryl-1,2,3-triazoles are easily generated. For example, geminal diazides derived from ketoesters, ketoamides, and ketones were converted under the reaction conditions.
View Article and Find Full Text PDFOrg Lett
September 2024
Key Laboratory of the Ministry of Education for Advanced Catalysis Materials, Institute of Advanced Fluorine-Containing Materials, Zhejiang Normal University, 688 Yingbin Road, Jinhua, Zhejiang 321004, People's Republic of China.
A highly efficient Au(I)-catalyzed cascade reaction between bispropargylic alcohols and pyridine--oxides has been realized. The reaction process involved a gold(I)-catalyzed sequential oxidation/Pinacol rearrangement/oxacyclization. Moreover, 1,2-aryl, 1,2-alkyl, or 1,2-vinyl migration was favored over 1,2-alkynyl in the crucial gold(I)-catalyzed Pinacol rearrangement step.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
December 2024
Department of Biological and Synthetic Chemistry, Centre of Biomedical Research, Sanjay Gandhi Postgraduate Institute of Medical Sciences Campus, Raebareli Road, Lucknow, 226014, INDIA.
The tetrahydroquinoline (THQ) framework is commonly found in natural products and pharmaceutically relevant molecules. Apart from using transition metal catalysts and chiral phosphoric acids, the chiral 2-substituted 1,2,3,4-THQs are synthesized using amine oxidase biocatalysts. However, the use of imine reductases (IREDs) in their asymmetric synthesis remained unexplored.
View Article and Find Full Text PDFOrg Lett
June 2024
Chemical Research & Development, Pfizer Worldwide Research & Development, Groton, Connecticut 06340, United States.
An efficient SAr approach for generating a wide array of 2-aryl and 2-alkyl pyrimidines in good to high yields was developed. This methodology does not require precious metal catalysts and is compatible with aryl, heteroaryl, and alkyl magnesium halides as nucleophiles. This process is scalable and performed at room temperature well below the temperature of the competing decomposition of the activated 2--butyl sulfonyl pyrimidine electrophile.
View Article and Find Full Text PDFBeilstein J Org Chem
November 2023
Center for Organic Photonics and Electronics and School of Chemistry and Biochemistry, Georgia Institute of Technology, Atlanta, GA 80007, United States.
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