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Visible-Light-Catalyzed Fast Synthesis of 1,4-Benzoxazepine Derivatives from 2-Alkoxyarylaldehydes and -Arylglycines.
J Org Chem
January 2025
Jiangxi Province Key Laboratory of Functional Organic Polymers, East China University of Technology, Nanchang 330013, China.
A novel photocatalytic method for the synthesis of 1,4-benzoxazepine using 2-alkoxyarylaldehyde as an oxygen source and -arylglycine as a nitrogen source has been reported. This method is mild, efficient, and fast, and the corresponding reaction can be completed within 2 h at room temperature under a nitrogen atmosphere and light-irradiation conditions. Mechanistic studies have confirmed that this scheme involves the decarboxylation cyclization of -arylglycine and provides a convenient pathway for the preparation of various 2-alkyl--phenyl-substituted 1,4-benzoxazepine.
View Article and Find Full Text PDFSynthesis of pyrano[3,2-]chromene-2,5-diones from 4-hydroxycoumarins and aminocrotonates under solvent-free conditions.
Org Biomol Chem
January 2025
Department of Natural Products & Medicinal Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad-500 007, India.
A new one-pot approach was developed for the construction of pyrano[3,2-]chromene-2,5-diones by reacting 4-hydroxycoumarins with ethyl 3-oxo-3-phenylpropanoates in the presence of ammonium salts or aminocrotonates under solvent-free conditions. The title compounds were formed by intramolecular cyclization through new C-C and C-O bonds. Structure assignment of compound 3e was confirmed by single crystal X-ray analysis.
View Article and Find Full Text PDFVisible-light-induced aerobic oxidative cyclization of nitroarenes with triethylamine using an organophotocatalyst.
Org Biomol Chem
January 2025
College of Chemistry, Xiangtan University, Xiangtan 411105, China.
Isoxazolidines are structurally important scaffolds in many natural products and bioactive compounds. Herein, we report a novel synthetic method for isoxazolidine derivatives through visible-light-induced photoredox cascade cyclization of nitroarenes with triethylamine under aerobic conditions. The resultant 5-hydroxyl isoxazolidine compounds were generally obtained in moderate yields with a broad range of compatible functionalities.
View Article and Find Full Text PDFAuthor Correction: Oxidative cyclization reagents reveal tryptophan cation-π interactions.
Nature
January 2025
Department of Chemistry, University of California, Berkeley, Berkeley, CA, USA.
Bioinspired concise synthesis of caged Sesquiterpenoids Artatrovirenols A and B.
Nat Commun
January 2025
State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, Gansu, PR China.
Artatrovirenols A and B are two newly isolated sesquiterpenoids with a complex caged framework. We report herein a concise synthesis of artatrovirenols A and B in 9 and 8 steps, respectively. The complex caged tetracycle is rapidly constructed from a known planar guaiane-type precursor through a bioinspired intramolecular [4 + 2] cyclization to firstly access artatrovirenol B, which is further transformed into artatrovirenol A through a biomimetic epoxidation-mediated lactonization reaction.
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