5-芳基四氮唑衍生物的高效合成方法与酯基的伴生降解有机化学.pdfVIP

DOI: 10.6023/cjoc201403051 研究简报 有机化学 Chinese Journal of Organic Chemistry NOTE 5-芳基四氮唑衍生物的高效合成方法与酯基的伴生降解 孙宏滨*,a 孙源华a 陈文龙b 秦 鹏a 齐 轩*,a (a 东北大学理学院 沈阳 110819) (b 攀钢集团研究院有限公司 钒钛资源综合利用国家重点实验室 攀枝花 617000) 摘要 以氯化铟为催化剂, 通过芳基腈和叠氮化钠的[3＋2]环加成反应合成了一系列 5-芳基四氮唑, 含各种官能团的 底物都可以获得高产率. 此合成方法还对酯的分解有催化效果, 可以在合成四氮唑的同时对酯进行脱保护获得羧酸和 醇. 关键词 氯化铟; 催化; 四氮唑; 合成; [3＋2]环加成; 酯分解 An Efficient Approach to the Synthesis of 5-Aryl-1H-tetrazole Derivatives Accompanying with the Cleavage of Ester Group Sun, Hongbin*,a Sun, Yuanhuaa Chen, Wenlongb Qin, Penga Qi, Xuan*,a a ( Department of Chemistry, Northeastern University, Shenyang 110819) b ( Pangang Group ResearchInstitude Co., Ltd., State Key Laboratory of Vanadium and Titanium Resources Comprehensive Utilization, Panzhihua 617000) Abstract 5-Phenyl-1H-tetrazoles were synthesized by catalytic [3＋2] cycloaddition with aryl nitriles and sodium azide. Indium trichloride was used as an efficient catalyst. The tetrazoles binding with varieties of functional groups were synthesized in good to quantitative yields. This tetrazole synthetic protocol also showed remarkable de-carboxylation activity. Esters were cleaved to carboxylic acids or alcohols in one pot. Keywords indium trichloride; catalysis; tetrazole; synthesis; [3 ＋2] cycloaddition; cleavage of ester 四氮唑被认为是一类重要的杂环化合物, 它们被广 锡基叠氮化物[14]和硼基叠氮化物[15]合成四氮唑也有报 泛应用