Understanding the Scope of Feist-Benary Furan Synthesis: Chemoselectivity and Diastereoselectivity of the Reaction Between -Halo Ketones and -Dicarbonyl Compounds

被引：20

作者：

Peng, Yi ^{[1
]}

Luo, Juan ^{[1
]}

Feng, Qiang ^{[2
]}

Tang, Qiang ^{[1
]}

机构：

[1] Chongqing Med Univ, Chongqing Res Ctr Pharmaceut Engn, Chongqing Key Lab Biochem & Mol Pharmacol, Coll Pharm,Fac Lab Med, 1 Yixueyuan Rd, Chongqing 400016, Peoples R China

[2] Chengdu Normal Univ, Coll Chem & Life Sci, 99 Haike Rd Eastern Sect, Chengdu 611130, Sichuan Provinc, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2016年 / 2016卷 / 30期

关键词：

Synthetic methods; Cyclization; Aldol reactions; Chemoselectivity; Oxygen heterocycles; Nitrogen heterocycles; PAAL-KNORR REACTION; ETHYL-ESTER DERIVATIVES; TETRASUBSTITUTED FURANS; HETEROCYCLIC-COMPOUNDS; CONVENIENT SYNTHESIS; EFFICIENT SYNTHESIS; SUBSTITUTED FURANS; ALPHA-HALOKETONES; ACID-DERIVATIVES; ANTITUMOR AGENTS;

D O I：

10.1002/ejoc.201600975

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Feist-Benary furan synthesis, the reaction between -halocarbonyl and -dicarbonyl compounds, has been known as an efficient method for generating many different types of furans containing a carbonyl group at C-3. However, it has also been reported that, under similar reaction conditions, intermediate tricarbonyl species could be further converted to alternative furan isomers through the application of a Paal-Knorr synthesis. In this manuscript, we investigate the chemoselectivity and diastereoselectivity of furan synthesis from -halo ketones and -dicarbonyl compounds, by carrying out the separation and characterization of the intermediates involved in the reaction. Additionally, a one-pot Feist-Benary furan synthesis from -halo ketones and -dicarbonyl compounds without any base or solvent has also been developed.

引用

页码：5169 / 5179

页数：11

共 86 条

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