Department of Chemistry, University of Minnesota, 207 Pleasant St., SE, Minneapolis, Minnesota, 55455, USA.
Published: June 2015
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Article Abstract
We report here thermal reactions between furan and one of three related triyne substrates. Each triyne is capable of reacting initially in two modes: (i) hexadehydro-Diels-Alder (HDDA) reaction or (ii) Diels-Alder reaction between one of its alkynes with furan. The relative rates of these initial events are such that two of the substrates react essentially in only one of modes (i) or (ii). The third is intermediate in behavior; its bifurcation is dependent on the concentration of the furan reactant. These results teach, more generally, principles relevant to the design of efficient HDDA-based reaction cascades.
Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecular-Based Materials, School of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, China.
The biological activities of natural products (NPs) provided precious resources for the development of new drugs. Numerous studies have shown that statins exhibit cytotoxic potential, which is now an extensive focus of investigation. Herein, a remarkably efficient method for modification of statins using hexadehydro-Diels-Alder (HDDA) arynes has been described.
Researchers created new ferrocenyl-related compounds using a chemical reaction between arynes and ferrocenyl oxazolines under mild conditions.
Water played a surprising role in rearranging these compounds into quinoline structures, while theoretical calculations confirmed the processes involved.
This study introduces two new methods that enhance the interaction of ferrocenyl compounds with arynes, paving the way for innovative ferrocene derivative synthesis.
2:1 adducts arise from the reaction of 2,5-diaryl-1,3,4-oxadiazoles and benzynes generated from the hexadehydro-Diels-Alder (HDDA) reaction. Density functional theory computations support a mechanistic manifold that includes a concerted SAr process. Additionally, the benzyne trapping reaction of 2,5-dimethyl-1,3,4-oxadiazole affords an unusual acylimine-containing 2:1 adduct, which is the first case in which a dearomatized product has arisen from a HDDA reaction.
A cascade hexadehydro-Diels-Alder (HDDA)/[3 + 2] cycloaddition reaction between tetrayne and ,'-cyclic acylhydrazone is described. This strategy allows the efficient construction of fully substituted 2,3-dihydro-1-indazole scaffolds which have insecticidal activity against the third instar larvae of .
Laboratory of Functional Molecular Solids, Ministry of Education, Anhui Key Laboratory of Molecular-Based Materials, School of Chemistry and Materials Science, Anhui Normal University, Wuhu, Anhui 241000, China.
A method for the hydroalkynylation and catalytic cyclization reactions of hexadehydro-Diels-Alder-derived benzynes is described. Diethynylbenzene derivatives are generated in a one-step reaction trimethylsilyl-alkyne groups with benzyne formed by heating the appropriate tetrayne substrate. Trimethyl(phenylethynyl)silane loses TMS and binds to the electron-deficient site on HDDA-derived benzynes, and then phenanthrene was synthesized under mild reaction conditions by transition-metal-free, base promoted intramolecular cyclization.
