三组分“一锅法”合成苯并二氢吡喃衍生物

Three-component, one-pot synthesis of 2H-benzopyran derivatives

摘要: 报道了一种无金属参与下的三组分“一锅法”合成苯并二氢吡喃衍生物的方法. 以水杨醛、芳基亚磺酸钠、1-芳磺酰基烯丙基溴为原料，在1,8-二氮杂双环5.4.0十一碳-7-烯(DBU)作用下，经取代、Knoevenagel缩合、oxa-Michael加成三步反应，以51%～86%的产率合成了15个结构新型的3-芳磺酰基-2-芳磺酰甲基-2H-苯并吡喃衍生物，产物结构经¹H NMR、¹³C NMR和HRMS表征. 研究表明，该方法学具有较好的底物普适性，可以进行克级放大，为苯并二氢吡喃衍生物的合成提供了一种高效、反应条件温和、环境友好的合成方法.

Abstract: A protocol of three-component, one-pot synthesis of 2H-benzopyran derivatives is reported. Promoted by strong basic 1,8-diazabicyclo5.4.0undec-7-ene (DBU), salicylic aldehydes, sodium arylsulfinates and 3-bromoallyl-arylsulfones were reacted in the sequence of S-nucleophilic substitution, tandem Knoevenagel condensation/intramolecular oxa-Michael addition reactions to generate a series of 2,3-disubstituted-2H-benzopyran derivatives. Under optimized reaction conditions, 15 target products were prepared in 51%−86% yields. All products were newly synthesized and fully characterized by ¹H NMR, ¹³C NMR and HRMS. This method has the advantages such as high efficiency, mild reaction conditions and environmental friendliness.