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
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