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A facile and direct approach to 1-substituted 2,3-dihydroquinazolin-4(1)-ones has been developed Pd(II)-catalyzed one-pot cascade annulation of -substituted anilines with CO, NHOAc and aldehydes, and it features an intrinsic directing strategy, cheap and easily obtainable raw materials, low cost, high step economy and efficiency, broad substrate scope and good product diversity. This protocol has been successfully applied to the synthesis of glycozolone A and gram-level experiments. Based on the control experiments and the literature, the reaction mechanism was proposed.
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http://dx.doi.org/10.1039/d4ob00055b | DOI Listing |
Chem Commun (Camb)
September 2025
Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
A CFOH-catalysed tandem cyclization of -alkynylnaphthols and -quinone monoketals is disclosed. The CFOH catalyst activates alkynylnaphthol to generate an all-carbon tetrasubstituted VQM by nucleophilic addition to quinone monoketal (Michael addition). Furthermore, the CFOH catalyst triggers -quinone monoketal to generate an electrophilic oxocarbenium cation to be captured by -alkynylnaphthol regiospecifically, resulting in the formation of an all-carbon tetrasubstituted VQM, followed by an intramolecular cyclization to afford a series of 1-(3-arylbenzofuran-2-yl)naphthalen-2-ols.
View Article and Find Full Text PDFJ Org Chem
September 2025
School of Chemistry and Chemical Engineering, Zhejiang Sci-Tech University, Hangzhou 310018, China.
Rh(III)-catalyzed C-H bond activation and annulation of -pyrimidyl-substituted anilines with CF-imidoyl sulfoxonium ylides (TFISYs) have been disclosed, affording a variety of 2-trifluoromethylindolines that contain a quaternary carbon center. A cascade C-H imidoylmethylation, tautomerization, and intramolecular nucleophilic addition sequence is involved in the transformation. The reaction could be scaled up to 2 mmol.
View Article and Find Full Text PDFChem Commun (Camb)
August 2025
College of Chemistry and Materials, Jiangxi Normal University, Nanchang 330022, China.
Fluorinated organic molecules constitute compounds with well-known and potential applications in the chemical industry and many related areas. Accordingly, the synthesis of fluorinated compounds has emerged as one of the central tasks of modern organic synthesis. As valuable and versatile synthons, enaminones have displayed amazingly broad application in the designation of novel organic reactions.
View Article and Find Full Text PDFJ Org Chem
August 2025
Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi 221005, India.
A one-pot strategy has been developed for the efficient synthesis of highly functionalized dihydrothiophenes using β-ketosulfoxonium ylides, β-ketothioamides, and aldehydes. This cascade process involves C(sp)-H insertion, aldol condensation, and intramolecular 1,4-conjugate addition, forming C-S and C-C bonds efficiently. The method offers good to high yields, a broad substrate scope, structural diversity, and scalability.
View Article and Find Full Text PDFBMC Chem
August 2025
Key Laboratory of Natural Pharmaceutical and Chemical Biology of Yunnan Province, School of Chemistry and Resources Engineering, Honghe University, Mengzi, Yunnan, 661100, China.
An attractive approach for the preparation of pyrrolo[2,3-d]pyrimidines has been developed via I/DMSO promoted cascade annulation of 6-amino-1,3-dimethyluracil with aurones. The reaction involves Michael addition, iodination, intramolecular nucleophilic substitution, and spiro ring opening in one-step process, and affords a series of natural product analogues containing pyrrolo[2,3-d]pyrimidine in good yields (up to 99%). Additionally, this protocol exhibits the advantages of high atom economy, inexpensive catalyst, readily available materials, convenient operation and applicability for large-scale synthesis.
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