Zinc-assisted synthesis of imidazolium-tetrazolate bi-heterocyclic zwitterions with variable alkyl bridge length
Zinc-assisted synthesis of imidazolium-tetrazolate bi-heterocyclic zwitterions with variable alkyl bridge length
摘要
Zinc halide-complexed alkyl-bridged bi-heterocycles were obtained as zwitterions from the Click reaction of a series of N-cyanoalkyl-N-alkylimidazolium halide ionic liquids with sodium azide. Reaction optimization showed fast reaction times and milder conditions compared to conventional Click syntheses from neutral nitriles.
Zinc halide-complexed alkyl-bridged bi-heterocycles were obtained as zwitterions from the Click reaction of a series of N-cyanoalkyl-N-alkylimidazolium halide ionic liquids with sodium azide. Reaction optimization showed fast reaction times and milder conditions compared to conventional Click syntheses from neutral nitriles.
基金
supported by the US Air Force Office of Scientific Research (F49550-10-1-0521)
参考文献22
-
1Dernko ZP, Sharpless KB. Preparation of 5-substituted 1H-tetrazoles from nitriles in water. J Org Chem, 2001, 66(24): 7945-7950.
-
2Drab DM, Shamshina JL, Smiglak M, Hines CC, Cordes DB, Rogers RD. A general design platform for ionic liquld ions based on bridged multi-heterocycles with flexible symmetry and charge. Chem Com- mun, 2010, 46:3544-3546.
-
3Katritzky AR, Singh S, Kirichenko K, Smiglak M, Holbrey JD, Reichert WM, Spear SK, Rogers RD. In search of ionic liquids in- corporating azolate anions. Chem EurJ, 2006, 12:4630-4641.
-
4Smiglak M, Hines CC, Wilson TB, Singh S, Vincek AS, Kirichenko K, Katritzky AR, Rogers RD. Ionic liquids based on azolate anions. Chem Eur J, 2010, 16:1572-1584.
-
5Koldobskii GI. Strategies and prospects in functionalization of te- trazoles. Russ J Org Chem, 2006, 42:469-486.
-
6Drab DM, Smiglak M, Shamshina JL, Kelley SP, Schneider S, Haw- kins TW, Rogers RD. Synthesis of N-cyanoalkyl-functionalized im- idazolium nitrate and dicyanamide ionic liquids with a comparison of their thermal properties for energetic applications. New J Chem, 2011 35:1701-1717.
-
7Himo F, Demko ZP, Noodleman L, Sharpless KB. Mechanisms of tetrazole formation by addition of azide to nitriles. J Am Chem Soc, 2002, 124(41): 12210-12216.
-
8Amantini D, Beleggia R, Fringuelli F, Pizzo F, Vaccaro L. TBAF-catalyzed synthesis of 5-substituted 1H-tetrazoles under sol-ventless conditions. J Org Chem, 2004, 69(8): 2896-2898.
-
9Schnaidt B, Meid D, Kieser D. Safe and fast tetrazole formation in ionic liquids. Tetrahedron, 2007, 63(2): 492--496.
-
10Himo F, Demko ZP, Noodleman L, Sharpless KB. Why is tetrazole formation by addition of azide to organic nitriles catalyzed by zinc (II) salts? JAm Chem Soc, 2003, 125(33): 9983-9987.
-
1周建伟,苗郁.用KNO3／Al2O3合成N—烷基咪唑[J].平原大学学报,2000,17(4):29-29.
-
2卢文贯,王小兵,刘宏文,洪显兰.Two Coordination Polymers Constructed by Cd(Ⅱ) and Zn(Ⅱ) with in situ Generated 5-(3-Pyridyl)tetrazolate Ligand：Syntheses,Crystal Structures and Luminescence Properties[J].Chinese Journal of Structural Chemistry,2016,35(3):383-391.
-
3郭胜利,卢士香,徐文国.微波辅助溶胶-凝胶法一步合成纳米氧化锌及其催化降解性能研究[J].北京理工大学学报,2012,32(1):82-85. 被引量：6
-
4王磊,孙兴华.用KOH/Al_2O_3合成N-烷基咪唑[J].应用化学,1993,10(4):84-85. 被引量：15
-
5王西新,赵建玲,杨浩,陈文涛,朱智甲.N-烷基(C_4～C_(16))咪唑的合成[J].化学试剂,2001,23(5):306-307. 被引量：3
-
6骆亚,付露露,向景.Three New Zn(Ⅱ) Coordination Compounds Based on the in-situ Formed Tetrazolate Ligand: Syntheses, Crystal Structures and Luminescence Properties[J].Chinese Journal of Structural Chemistry,2015,34(1):95-102. 被引量：2
-
7何嘉俊,李翔,刘小成,刘昱,刘端.硼氢化锌还原苯乙酰胺的研究[J].化学与生物工程,2009,26(9):34-35. 被引量：1
-
8李西平.ZnH分子的量子化学计算[J].昆明工学院学报,1995,20(2):104-106.
-
9李西平,涂学炎.ZnNe低激发态的量子化学研究[J].物理化学学报,2000,16(3):238-242.
-
10卢向军,窦辉,戴耀东,陈达.磷酸酯盐离子液体的微波辅助合成及其在Knoevenagel反应中的应用[J].南京航空航天大学学报,2009,41(3):414-417. 被引量：6
