The first successful copper-catalyzed decarboxylative cyclization reaction of ethynylbenzoxazinones and thiols has been developed. A rarely studied α-addition process to a copper-allenylidene intermediate promoted this reaction. Using this protocol, a range of 2-thiomethylene indole compounds have been obtained. This methodology offers significant advantages including mild reaction conditions, cheap catalysts, good yields and broad substrate compatibility.
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http://dx.doi.org/10.1039/d4ob01164c | DOI Listing |
Chemistry
January 2025
Zhengzhou University, School of Pharmaceutical Sciences, 100 Science Avenue, 450001, Zhengzhou, CHINA.
An unprecedented formal [1+5] cyclization of indoline-derived azadienes with 1,3,5-triazinanes has been realized, providing a facile access to biologically important indoline-spiro-hexahydropyrimidines with good to excellent yields (up to 99% yield). Different from previous reports, this is the first study that indoline-derived azadienes could participate in cyclizations as one-atom synthons. This methodology is also distinguished by not involving any additive or catalyst, readily available starting materials, wide range of substrate applicability, operational simplicity and simultaneously reassembling two C-N and two C-C bonds in one-step reaction.
View Article and Find Full Text PDFAngew Chem Int Ed Engl
January 2025
Chinese Academy of Sciences Fujian Institute of Research on the Structure of Matter, State Key Laboratory of Structural Chemistry, 350108, Fuzhou, CHINA.
Here, we report the facile synthesis of imidazole-linked porous organic cages (IPOCs) via an in-situ cyclization reaction protocol. Specifically, three IPOCs with [2+4] lantern-like structures and one with a [3+6] triangular prism structure were successfully prepared through condensation reactions between tetraformyl-functionalized calix[4]arene and bis(o-phenylenediamine) monomers in a single pot. Notably, these IPOCs exhibit high porosity, with Brunauer-Emmett-Teller (BET) specific surface areas reaching up to 1162 m2 g-1.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
School of Chemical Engineering, Zhengzhou University, Zhengzhou 450001, China.
A visible-light-induced deoxygenative alkylation/cyclization of acrylamides with alcohols activated by CS has been developed by using xanthate salts as alkyl radical precursors in the presence of tricyclohexylphosphine. It proceeds through a tandem radical addition/cyclization process, and this protocol provides a reliable and practical approach to building the skeleton of 3,3-disubstituted oxindoles in moderate to good yields. Notable features of this reaction include readily available starting reagents, broad substrate scope and mild reaction conditions.
View Article and Find Full Text PDFChemistry
January 2025
Ruprecht Karls Universitat Heidelberg, Organisch-Chemisches Institut, Im Neuenheimer Feld 270, 69120, Heidelberg, GERMANY.
Here we present a simple gold-catalyzed one-pot reaction of easily available diarylbutadiynes, with trimethoxybenzene as solvent and reactant to synthesize 4,6,8-trimethoxyazulenes. The methoxy substituents, which render the azulene very electron-rich, enable a change of azulenes typical regioselectivity for electrophilic substitutions, which enables facile electrophilic 2-substitution with iodine, bromine, chlorine, selenium or sulfur. Especially the 2-haloazulenes which can usually only be obtained through lengthy multistep syntheses are valuable building blocks for the synthesis of 2-substituted azulene derivatives.
View Article and Find Full Text PDFOrg Biomol Chem
January 2025
Univ Rennes, CNRS, ISCR - UMR 6226, F-35000 Rennes, France.
A straightforward and highly diastereoselective synthesis of -4-hydroxypiperidines is presented. This method allows access to C2 and C4 substituted piperidines, bearing a tetrasubstituted carbon stereocenter at C4. -Disubstituted homoallylic amines and ketoaldehydes as carbonyl partners have been rarely used in aza-Prins cyclizations, expanding the scope of this reaction.
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