NHOAc/PdCl/CuCl mediated domino double cyclocondensation of α-sulfonyl -hydroxyacetophenones and 2-allylbenzaldehydes provides tetracyclic sulfonyl dihydrobenzo[]xanthen-7-one core with good to excellent yields in MeOH. The intermediates contain a 3-sulfonyl flavanone motif. Only water is generated as a byproduct. The use of various catalysts and reaction conditions is studied for the facile-operational conversion.
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http://dx.doi.org/10.1021/acs.joc.9b02387 | DOI Listing |
Org Biomol Chem
January 2025
Department of Medicinal and Applied Chemistry, Kaohsiung Medical University, Kaohsiung 807, Taiwan.
We report the synthesis of six-membered saturated and unsaturated 1,4-oxasulfone derivatives rongalite-mediated intermolecular double sulfination of α-bromoacetophenone. This was followed by Bi(OTf)-catalyzed intramolecular condensation of 1,3-diaroylsulfones under open-vessel conditions. Furthermore, the chemical structures of the key products were determined through single-crystal X-ray analyses.
View Article and Find Full Text PDFJ Org Chem
October 2023
Indian Institute of Technology Hyderabad, Kandi, Sangareddy, Telangana 502 284, India.
Developing mild and effective synthetic strategies for producing significant molecules starting from readily available starting materials is indispensable in organic synthesis. Herein, we present a triflic acid-driven dual cyclization pathway to produce functionalized indeno[2,1-]chromen-6(7)-ones from simple 2-formyl (or 2-acyl) cinnamate esters and phenols. Notably, this protocol enabled the construction of two C-C bonds and one C-O bond under metal-free reaction conditions the activation of the unreactive ester moiety in a single pot.
View Article and Find Full Text PDFOrg Biomol Chem
October 2023
Department of Chemical Engineering, Faculty of Technology & Engineering, The Maharaja Sayajirao University of Baroda, Vadodara-390 001, Gujarat, India.
An interesting molecular architecture, butterflyene, resembling the shape of a butterfly has been synthesized a sequence of cyclocondensation, benzylic oxidation, McMurry coupling and Diels-Alder reaction (DAR), successively. The DAR of the tetrasubstituted double bond of a bicyclopentylidene moiety with various dienes has been performed to prepare the analogues of butterflyene. DFT calculations have also been used to analyze the structural optimization and reaction energies.
View Article and Find Full Text PDFOrg Biomol Chem
November 2022
Saint Petersburg State University, Saint Petersburg 199034, Russian Federation.
The Castagnoli-Cushman reaction of oximes, discovered originally for homophthalic anhydride, stimulated the search for other cyclic anhydrides that would be workable in that reaction. Finally, 3-arylglutaconic acid anhydrides were identified as displaying the right reactivity towards a wide range of oximes (including those which did not react with homophthalic anhydride, such as derivatives of aliphatic aldehydes or ketones and substrates with nucleophilic side groups) and delivering, after 18 h at 110 °C in DMSO, β,γ-unsaturated -hydroxylactam products lacking the carboxylic acid functionality as the result of decarboxylation accompanying the cyclocondensation process. The reaction was found to be scalable to gram quantities of the starting anhydrides.
View Article and Find Full Text PDFMolecules
September 2022
ELKH-SZTE, Stereochemistry Research Group, University of Szeged, Eötvös utca 6, 6720 Szeged, Hungary.
-heterocyclic compounds, such as quinazolinone derivatives, have significant biological activities. Nowadays, as the demand for environmentally benign, sustainable processes increases, the application of compounds from renewable sources, easily separable heterogeneous catalysts and efficient, alternative activation methods is of great importance. In this study, we have developed a convenient, green procedure for the preparation of 3a-methyl-2,3,3a,4-tetrahydropyrrolo[1,2-]quinazoline-1,5-dione through a double cyclocondensation cascade using anthranilamide and ethyl levulinate.
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