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The extent to which benzynes react with various trapping agents is an important question in synthetic chemistry due to its versatility to produce products that can be used as pharmaceuticals, dyes and other complex molecules. The hexadehydro-Diels-Alder (HDDA) reaction allows the generation of benzynes in situ which then can be efficiently trapped to synthesize complex products in one step with high yields. Reactions of HDDA - derived benzynes with trapping agents such as thioamides, alcohols, pyrroles, silyl ethers and multifunctional natural products have been studied in previous research. In this research, the reactions of HDDA-derived benzynes with diaziridines is explored because it is possible to form indoles as the final product; indole derivatives play an important role in pharmacological drug discovery and analysis, such as in its use for anticancer, antiHIV and antidiabetic pharmaceuticals. The synthesis, characterization and investigation of several benzyne precursors, diaziridines, and their corresponding reactions were examined in this research along with the optimization of the reaction conditions for the synthesis of diaziridines.

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Benzynes; Organic compounds--Synthesis; Hexadehydro-Diels-Alder (HDDA) reaction; Diaziridines; Indoles


Organic Chemistry

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Conference Proceeding

Intermolecular-Trapping of 1,3-Dialkyl Diaziridines with HDDA-Derived Benzynes