A cascade reaction of indoles with propargylic diols involving an unprecedented metal-free 1,2-indole migration onto an alkyne was carried out. DFT calculations support a mechanism consisting of a concerted nucleophilic attack of the indole nucleus with loss of water, followed by the 1,2-migration and subsequent Nazarov cyclization. This Brønsted acid-catalyzed protocol affords indole-functionalized benzofulvene derivatives in high yields.
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http://dx.doi.org/10.1002/chem.201502174 | DOI Listing |
Curr Top Med Chem
January 2025
Department of Pharmaceutical Chemistry, JSS College of Pharmacy, JSS Academy of Higher Education & Research (JSS AHER), Mysuru, Karnataka, India.
Background: Several chemical studies described the physiological efficacy of 1,4- dihydropyridines (DHPs). DHPs bind to specific sites on the α1 subunit of L-type calcium channels, where they demonstrate a more pronounced inhibition of Ca2+ influx in vascular smooth muscle compared to myocardial tissue. This selective inhibition is the basis for their preferential vasodilatory action on peripheral and coronary arteries, a characteristic that underlies their therapeutic utility in managing hypertension and angina.
View Article and Find Full Text PDFACS Appl Mater Interfaces
January 2025
Functional Nanomaterials Laboratory, Center for Micro/Nanomaterials and Technology, and Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
Antireflection (AR) coatings with mechanical robustness and superhydrophobic properties have wide potential applications in optical, electronic, and automotive fields. However, the fabrication of large-sized, robust, and multifunctional AR coatings on plastic/polymer substrates has been a challenging problem. In this study, we developed a bottom-up approach to produce mechanically robust, enhanced transmittance, and superhydrophobic coatings on poly(methyl methacrylate) (PMMA) substrate.
View Article and Find Full Text PDFChemistry
December 2024
Eotvos Lorand University, Organic Chemistry, Pazmany Peter Setany 1/A, 1117, Budapest, HUNGARY.
The present study reveals an unexpected anomaly observed in the acid-catalyzed hydrolysis of the 5,6-O-isopropylidene group in 3-O-protected D-gluco- and D-allofuranose derivatives. Although the removal of the 5,6-O-isopropylidene protecting group is typically rapid and quantitative under acidic conditions, an unexpected inhibition of this reaction is observed for the two C3-epimers, 3-O-imidazole sulfonyl moiety. X-ray data show a two-faced imidazole ring orientation in the crystal, while solution state NOE data reveal a critical interaction type between the isopropylidene and the imidazole rings.
View Article and Find Full Text PDFOrg Lett
December 2024
Department of Life Science and Applied Chemistry, Graduate School of Engineering, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya 466-8555, Japan.
Herein, we present the enantioselective synthesis of 2,3-dihydro-4-quinolones bearing chiral tetrasubstituted carbons from isatins and 2'-aminoacetophenones. The transformation is mediated by a chiral phosphoric acid catalyst and proceeds via an generated ketimine and subsequent enantioselective intramolecular cyclization. The methodology features a broad scope and functional group tolerance with yields and enantioselectivities of up to 99% and 98% ee.
View Article and Find Full Text PDFChemSusChem
December 2024
University of New England, School of Science and Technology, 1 Elm Avenue, 2351, Armidale, AUSTRALIA.
Levoglucosenone is an important platform chemical and the principal product of acid-catalyzed cellulose pyrolysis, formed through several intermediates including levoglucosan. An acid-catalyzed redox isomerization of substituted 6,8-dioxabicyclo[3.2.
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