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

页码：5569 / 5572

页数：4

共 76 条

[51] Discovery of 2-aminobuta-1,3-enynes in asymmetric organocascade catalysis: construction of drug-like spirocyclic cyclohexanes having five to six contiguous stereocenters [J].