Synthesis of benzofurans via an acid catalysed transacetalisation/Fries-type O → C rearrangement/Michael addition/ring-opening aromatisation cascade of β-pyrones

被引：22
作者：
Bankar, Siddheshwar K. [1 ]
Mathew, Jopaul [1 ]
Ramasastry, S. S. V. [1 ]
机构：
[1] Indian Inst Sci Educ & Res IISER Mohali, Dept Chem Sci, Organ Synth & Catalysis Lab, Sect 81,Manuali PO, Sas Nagar, Punjab, India
来源：
CHEMICAL COMMUNICATIONS | 2016年 / 52卷 / 32期
关键词：
STEREOSELECTIVE-SYNTHESIS; BIOLOGICAL-ACTIVITY; ARYL; DERIVATIVES; GLYCOSIDE; CONSTRUCTION; CYCLIZATION; COUMARINS; CHEMISTRY; GLYCOSYLATION;
D O I：
10.1039/c6cc01016d
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
An unusual and facile approach for the synthesis of 2-benzofuranyl-3-hydroxyacetones from 6-acetoxy-beta-pyrones and phenols is presented. The synthetic sequence involves a cascade transacetalisation, Fries-type O -> C rearrangement followed by Michael addition and ring-opening aromatisation. The versatility of this method was further demonstrated via the synthesis of 4,4a-dihydropyrano[3,2-b]benzofuran-3-ones, furo[3,2-c]coumarins, and spiro[benzofuran-2,2'-furan]-4'-ones. The unexpected cascade event would also provide new possible considerations in the beta-pyrone-involved organic synthesis.
引用
收藏
页码：5569 / 5572
页数：4
相关论文
共 76 条
[71]   Sweet (hetero)aromatics: glycosylated templates for the construction of saccharide mimetics [J].
Wiebe, Christine ;
Schlemmer, Claudine ;
Weck, Stefan ;
Opatz, Till .
CHEMICAL COMMUNICATIONS, 2011, 47 (32) :9212-9214
[72]   Stereoselective Synthesis of Vinyl Triflones and Heteroaryl Triflones through Anionic O→Cvinyl and N→Cvinyl Trifluoromethanesulfonyl Migration Reactions [J].
Xu, Xiu-Hua ;
Taniguchi, Misaki ;
Wang, Xin ;
Tokunaga, Etsuko ;
Ozawa, Tomohiro ;
Masuda, Hideki ;
Shibata, Norio .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (48) :12628-12631
[73]   Identification of Bitter Modulating Maillard-Catechin Reaction Products [J].
Zhang, Liyun ;
Xia, Youlin ;
Peterson, Devin G. .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2014, 62 (33) :8470-8477
[74]   Flavonoid ketohexosefuranosides from the leaves of Crataegus pinnatifida Bge. var. major NEBr. [J].
Zhang, PC ;
Xu, SX .
PHYTOCHEMISTRY, 2001, 57 (08) :1249-1253
[75]   Copper(II) bromide-catalyzed intramolecular decarboxylative functionalization to form a C(sp3)-O bond for the synthesis of furo[3,2-c]-coumarins [J].
Zhang, W. L. ;
Yue, S. N. ;
Shen, Y. M. ;
Hu, H. Y. ;
Meng, Q-H. ;
Wu, H. ;
Liu, Y. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (12) :3602-3609
[76]   Copper-Catalyzed Synthesis of Furo[3,2-c]coumarins and Dihydrofuro[3,2-c]coumarins through a Propargylation/Alkyne Oxacyclization/Isomerization Cascade under Microwave Irradiation [J].
Zhang, Xiao-Yan ;
Hu, Li-Li ;
Shen, Ze ;
Chen, Zhong-Zhu ;
Xu, Zhi-Gang ;
Li, Shi-Qiang ;
Xie, Jian-Wu ;
Cui, Hai-Lei .
SYNLETT, 2015, 26 (20) :2821-2825
12345678