A Brønsted acid-catalyzed (4 + 3) cyclization of N, N'-cyclic azomethine imines with isatoic anhydrides has been discovered, which constructs seven-membered nitrogenous heterocyclic frameworks with overall high yields (up to 98% yield). This reaction represents a rarely reported (4 + 3) cyclization of N, N'-cyclic azomethine imines, which involves the reassembly of a C-N bond. In addition, this reaction has also accomplished the unprecedented (4 + 3) cyclization of isatoic anhydrides.
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http://dx.doi.org/10.1021/acs.orglett.8b03604 | DOI Listing |
Org Lett
November 2023
State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin 541004, China.
Azomethine imines, broadly known as 1,3-dipoles, efficiently produce synthetically and biologically significant dinitrogen-fused heterocycles via predominantly concerted or ionic pathways. Herein, we describe a radical-based annulation of azomethine imines utilizing visible-light photoredox catalysis for the first time. This strategy enables the synthesis of dinitrogen-fused saturated six-membered cyclic products that have traditionally been difficult to access.
View Article and Find Full Text PDFOrg Lett
October 2023
Department of Nuclear Medicine, Zhongnan Hospital of Wuhan University, School of Pharmaceutical Sciences, Wuhan University, Wuhan 430071, China.
Phys Chem Chem Phys
May 2019
National Research Tomsk State University, 36, Lenin Avenue, Tomsk, 634050, Russia.
The reactions of glyoxal with ammonia, ammonium salts, and amines cause the formation of the secondary organic aerosol (SOA) components (imidazole and its derivatives) in the atmosphere. The interaction of glyoxal and ammonia in aqueous solution is a primary reaction for these processes, and the explanation of its mechanism will allow developing the methods to control the formation of the SOA components. A detailed mechanism for the formation of key intermediates, namely, ethanediimine, diaminoethanediol, and aminoethanetriol, required for the imidazole ring cyclization, is proposed, and its potential energy surface (PES) has been constructed.
View Article and Find Full Text PDFOrg Lett
February 2019
School of Chemistry and Materials Science , Jiangsu Normal University, Xuzhou 221116 , China.
A Brønsted acid-catalyzed (4 + 3) cyclization of N, N'-cyclic azomethine imines with isatoic anhydrides has been discovered, which constructs seven-membered nitrogenous heterocyclic frameworks with overall high yields (up to 98% yield). This reaction represents a rarely reported (4 + 3) cyclization of N, N'-cyclic azomethine imines, which involves the reassembly of a C-N bond. In addition, this reaction has also accomplished the unprecedented (4 + 3) cyclization of isatoic anhydrides.
View Article and Find Full Text PDFChem Commun (Camb)
March 2018
School of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006, China.
Herein, a copper-catalyzed highly diastereoselective aerobic oxygenated [3+3] cyclization of 3-substituted indoles with C,N-cyclic azomethine imines using oxygen as the sole oxidant under mild conditions has been developed. This protocol provides a simple and convenient approach for constructing [2,3]-fused indoline O-heterocycles bearing two pharmaceutically intriguing parts, tetrahydroisoquinoline and indoline. Good yields and excellent diastereoselectivity under mild reaction conditions were observed.
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