A base-promoted tandem SAr/Boulton-Katritzky rearrangement is developed. It offers a simple and straightforward method for the formation of functionalized [1,2,4]triazolo[1,5-]pyridines from 1,2,4-oxadiazol-3-amines or 3-aminoisoxazoles with 2-fluoropyridines.
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http://dx.doi.org/10.1021/acs.orglett.2c00863 | DOI Listing |
Org Biomol Chem
December 2024
Department of Applied Chemistry, School of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816, P. R. China.
A KCO-promoted tandem ring-opening/ring-closing of -alkynyl-2-oxazolidinones has been described, affording 2-oxazolines in 42-99% yields without column chromatography isolation. This operationally simple reaction proceeds under ambient conditions without a transition-metal catalyst and an external oxidant and can be applied for the late-stage functionalization of biologically active compounds.
View Article and Find Full Text PDFJ Org Chem
October 2024
Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510641, China.
Herein, a base-promoted strategy for the synthesis of β-amino acids derivatives from α,β-unsaturated acyl chlorides derivatives and aryl amines has been described. In the presence of triethylamine, a tandem Michael addition and nucleophilic substitution progress was generated. The current method features readily available raw materials, mild reaction conditions, high atom economy, and wide tolerance for the coupling partners.
View Article and Find Full Text PDFOrg Lett
September 2024
Key Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan 411105, P. R. China.
A novel and unique approach for the construction of polysubstituted pyrimido[4,5-]indoles from 2-(indol-3-yl)naphthoquinones and benzamidines is described. Our strategy, promoted by an inorganic base, involves the ring opening and recyclization of naphthoquinone and produces three nitrogen heterocyclic rings via multiple C-N bond formations in one pot under transition-metal-free conditions.
View Article and Find Full Text PDFJ Org Chem
May 2024
School of Pharmaceutical Sciences, Hangzhou Medical College, Hangzhou, Zhejiang 311399, China.
A convenient method for preparing 3-aryl isoquinolines via a base-promoted tandem reaction is presented. Simply combining commercially available 2-methyl-arylaldehydes, benzonitriles, NaN(SiMe), and CsCO enabled the synthesis of a variety of isoquinolines (23 examples, ≤90% yield). Among the syntheses of isoquinolines, the transition metal-free method described here is straightforward, practical, and operationally simple.
View Article and Find Full Text PDFBeilstein J Org Chem
March 2024
Institute of Chemistry, Saint Petersburg State University, 26 Universitetskiy pr., Peterhof, Saint Petersburg 198504, Russian Federation.
A facile approach to novel medicinally relevant spiro heterocyclic scaffolds (namely furan-2(5)-ones, tetrahydrofurans and pyrans spiro-conjugated with the succinimide ring) has been developed. The protocol consists of Rh(II)-catalyzed insertion of heterocyclic carbenes derived from diazoarylidene succinimides (DAS) into the O-H bond of propiolic/allenic acids or brominated alcohols, followed by base-promoted cyclization to afford the target spirocyclic compounds in good to high yields.
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