A FACILE SYNTHESIS OF 4-ARYL-1,1,1-TRIFLUOROBUT-3-EN-2-ONES VIA 4-ARYL SUBSTITUTED CF3 - CONTAINING DIHYDROPYRAN DERIVATIVES: A VERSATILE METHOD FOR THE INTRODUCTION OF FLUORINE-CONTAINING C4- AND C6- UNIT TO AROMATIC COMPOUNDS

被引：4

作者：

Ota, Norio ^{[1
]}

Okada, Etsuji ^{[1
]}

Shibata, Dai ^{[1
]}

Adachi, Satoru ^{[1
]}

Saikawa, Shohei ^{[1
]}

机构：

[1] Kobe Univ, Dept Chem Sci & Engn, Grad Sch Engn, Nada Ku, Kobe, Hyogo 6578501, Japan

来源：

HETEROCYCLES | 2010年 / 80卷 / 01期

关键词：

Dihydropyran; Retro Hetero Diels-Alder Reaction; Trifluoroacetylvinylation; 4-Trifluoroacetyl-1,3-butadienylation; Electrocyclic Ring-Opening; C-BOND FORMATION; ORGANIC-SYNTHESIS; SULFIDES; AMINES; ETHERS;

D O I：

10.3987/COM-09-S(S)60

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The CF3 - containing dihydropyran derivative (2) reacted easily with various aromatic compounds in trifluoroacetic acid to give novel 4-aryl substituted dihydropyran derivatives (7) in moderate to high yields. Retro hetero Die Is-Alder reaction of thus obtained 7 proceeded readily by heating at 300 degrees C to afford the corresponding 4-aryl-1,1,1-trifluorobut-3-en-2-ones (12) in good to excellent yields. With the use of p-toluenesulfonic acid instead of trifluoroacetic acid together with dihydropyran (2) in acetonitrile, 4-trifluoroacetyl-1,3-butalienylation of 1,3-dimethoxybenzene occurred successfully. The bimolecular reaction of dihydropyran (2) in the presence of p-toluenesulfonic acid was also examined.

引用

页码：515 / 525

页数：11

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