Alkylation of 1,2,3-benzotriazole with iodomethyl ketones

作者:Shagun L G*; Dorofeev I A; Tokareva I A; Larina L I; Voronkov M G
来源:Russian Journal of Organic Chemistry, 2012, 48(12): 1561-1563.
DOI:10.1134/S1070428012120111

摘要

Solvent-free reactions of 1,2,3-benzotriazole with 1-iodopropan-2-one and 1,3-diiodopropan-2-one in the absence of a catalyst involved alkylation of the heteroring at the N-1 atom and subsequent quaternization at the N-3 atom with formation of 1,3-bis(2-oxopropyl)-1H-1,2,3-benzotriazolium triiodide which is a new conducting ionic liquid. The reaction of 1,2,3-benzotriazole with 1,3-diiodopropan-2-one was accompanied by reductive deiodination of the iodomethyl groups in the initial ketone with hydrogen iodide liberated by N-1-alkylation. Triiodide ion readily exchanges for nitrate ion by the action of AgNO3 to produce 1,3-bis(2-oxopropyl)-1H-1,2,3-benzotriazolium nitrate. The reaction of 1,2,3-benzotriazole with 2-iodo-1-phenylethan-1-one in melt resulted in the formation of 1,3-bis(2-oxo-2-phenylethyl)-1H-1,2,3-benzotriazolium triiodide.

  • 出版日期2012-12

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