A novel and efficient multicomponent cyclization of methyl ketones, cyanamides, and arylamines for the synthesizing 2,4-diamino-1,3,5-triazines via consecutive formation of four C-N bonds is reported. This multicomponent reaction is characterized by the employment of two molecules of cyanamide for double C(sp)-H amination of methyl ketones, avoiding complicated prepreparation of substrates and expanding the substrate scope. Furthermore, this multicomponent cyclization strategy provides a new approach for generating diverse 2,4-diamino-1,3,5-triazines with a broad substrate scope under mild conditions.
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http://dx.doi.org/10.1021/acs.orglett.0c03130 | DOI Listing |
Org Lett
December 2024
State Key Laboratory of Green Pesticide, Engineering Research Center of Photoenergy Utilization for Pollution Control and Carbon Reduction, College of Chemistry, Central China Normal University, Wuhan, 430070, China.
A multicomponent heterogeneous semiconductor photocatalytic sulfinylsulfonylation of alkenes with alkyl iodides and SO was displayed under mild metal-free conditions by using boron carbonitride (BCN) as the alternative photocatalyst. This approach has resulted in the production of a wide range of structurally diverse sultine products in moderate to high yields, using readily available starting materials including alkyl iodides and olefins with broad functional group tolerance. The method is also suitable for the late-stage functionalization of complex bioactive molecules.
View Article and Find Full Text PDFOrg Lett
December 2024
Institute of Advanced Studies and School of Pharmaceutical Sciences, Taizhou University, Jiaojiang, Zhejiang 318000, China.
We developed a molecular-oxygen-mediated multicomponent oxidative cyclization strategy to synthesize -heterocycles containing tertiary alcohol units via the formation of key C-OH bonds and quaternary carbon centers. This formal [3 + 2 + 1] annulation offers a green and sustainable alternative for the C-OH bond formation, using O as both the oxidant and oxygen source under metal- and catalyst-free conditions. Notably, continuous [1,5]-hydrogen transfer together with excess alcohols promotes the formation of C-OH-bearing products.
View Article and Find Full Text PDFChem Rec
November 2024
Universidade Federal Fluminense, Instituto de Química, Departamento de Química Orgânica, Programa de Pós-Graduação em Química, 24020-141, Niterói, Rio de Janeiro, Brazil.
J Org Chem
December 2024
Key Laboratory of Chemistry in Ethnic Medicinal Resources, Key Laboratory of Natural Products Synthetic Biology of Ethnic Medicinal Endophytes, School of Ethnic Medicine, Yunnan Minzu University, Kunming, 650500, China.
A multicomponent [2+2+1] tandem cyclization of alkynones with amines and water using potassium thiocyanate as electrolyte and raw material to access thiazol-2(3)-ones has been developed. This transformation proceeded smoothly via electrocatalytic oxidative C-H bond thiolation, and nucleophilic cascade cyclization to build the (C-S/C-N) bonds to construct the C-O bond. The reaction avoided using transition metal catalysts or oxidation reagents, making it more sustainable and renewable.
View Article and Find Full Text PDFJ Org Chem
November 2024
Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow 226031, India.
We report a new method to create enantioenriched azatricycles using chiral α-amino acids in a two-step process after an Ugi reaction. Amino acids are great building blocks for making pure chiral molecules. Using chiral natural molecules in multicomponent reactions (MCRs) helps increase their variety by adding new chiral centers.
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