[reaction: see text] 3-Halogeno-4-methoxybenzynes 5 generated from 5-(3-halogeno-4-methoxyphenyl)thianthrenium perchlorates 1 and LDA in THF at reflux reacted with various beta-amino carbonyl compounds and 2-aminophenyl benzenesulfonate etc. to give diverse heterocyclic compounds.
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http://dx.doi.org/10.1021/jo050420c | DOI Listing |
Anal Chem
January 2025
Department of Chemistry and Biochemistry, The Ohio State University, Columbus, Ohio 43210, United States.
This study describes a microfluidic thread-based analytical device (μTAD) capable of in situ mass spectrometric analysis for continuous flow reaction monitoring. Organic reaction screening is foundational to drug discovery. Microfluidic devices are of special interest here because they provide continuous reaction monitoring with advantages such as the use of smaller reagent volumes and short analysis times.
View Article and Find Full Text PDFSci Rep
December 2024
Department of Organic and Polymer Chemistry, Faculty of Chemistry, Kharazmi University, Tehran, 15719-14911, Iran.
This study investigates the repurposing of asphaltene, a petroleum waste product, as a catalyst for organic reactions. Sulfonated asphaltene was synthesized and evaluated for its efficacy in catalyzing the Mannich reaction, displaying notable diastereoselectivity and operating effectively under mild conditions. Characterization of the catalyst's chemical composition, structure, and thermal stability was conducted using FT-IR, TGA, XRD, CHN, BET-BJH, SEM, and EDS analyses.
View Article and Find Full Text PDFACS Omega
July 2024
School of Life and Medical Sciences, University of Hertfordshire, Hatfield, AL10 9AB, United Kingdom.
Glioblastoma (GB) is an aggressive brain malignancy characterized by its invasive nature. Current treatment has limited effectiveness, resulting in poor patients' prognoses. β-Amino carbonyl (β-AC) compounds have gained attention due to their potential anticancerous properties.
View Article and Find Full Text PDFJ Org Chem
July 2024
Department of Chemistry, UNC College of Arts and Sciences, University of North Carolina at Chapel Hill, Chapel Hill, North Carolina 27599, United States.
Bifunctional thiourea-based organocatalysts facilitate an enantioselective desymmetrization and Lossen rearrangement cascade reaction of -sulfoxy -succinimides, resulting in the synthesis of cyclic β-amino acid derivatives. This catalytic system was optimized for bicyclic and tricyclic succinimide substrates affording yields from 61-91% and up to 96:4 er. This reaction proceeds via the group selective addition of the primary alcohol nucleophile to an enantiotopic carbonyl group with sequential rearrangement of the intermediate -sulfonyl hydroxamate ester.
View Article and Find Full Text PDFRSC Adv
May 2024
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College Beijing 100050 China
Cyclic -sulfonyl aldimines are well-known aza-[2]-synthons for various [2 + ] annulation reactions. Herein we describe a novel base mediated [2 + 1] annulation and a regioselective aziridine ring-opening reaction cascade, which provides an efficient and distinct synthetic strategy from readily available cyclic -sulfonyl aldimines and -carbonyl sulfonium salts leading to -amino ketone derivatives through the corresponding fused tri-substituted aziridines. This one-pot, two-step process involves formation of C-C and C-N bonds and subsequent cleavage of a C-N bond.
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