An Approach to the Synthesis of 1-Propenylnaphthols and 3-Arylnaphtho[2,1-b]furans.
A simple and efficient strategy for the synthesis of 1-propenylnaphthols from readily accessible 3-arylallylnaphthyl ethers has been developed. By using K2CO3as base and 2-methoxyethanol as solvent, direct access to a wide range of 1-propenylnaphthols can be achieved in generally good yield (up to 99%) with high stereoselectivity toward the Z isomer. The control experiments indicate that the reaction proceeds through a sequential Claisen rearrangement/isomerization process. Furthermore, starting from the same material, the highly valuable 3-arylnaphtho[2,1-b]furans can be obtained in N,N-dimethylformamide and in the presence of Ag2O as the oxidant via a one-pot sequential Claisen rearrangement/isomerization/cyclization reaction. Mechanistic studies confirm that 1-propenylnaphthols are the key intermediates to form the 3-arylnaphtho[2,1-b]furans. In addition, these two operationally simple and practical protocols could be scaled up to a gram level.
Key Lb of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University , Chengdu 610064, People's Republic of China.
Jin
J
Huang
State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, West China Medical School, Sichuan University , Chengdu 610064, People's Republic of China.
Wei
W
Wang
Key Lb of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University , Chengdu 610064, People's Republic of China.
Hai-Yu
HY
He
Key Lb of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University , Chengdu 610064, People's Republic of China.
Lei
L
Jian
Key Lb of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University , Chengdu 610064, People's Republic of China.
Hai-Yan
HY
Fu
Key Lb of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University , Chengdu 610064, People's Republic of China.
Xue-Li
XL
Zheng
Key Lb of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University , Chengdu 610064, People's Republic of China.
Hua
H
Chen
Key Lb of Green Chemistry and Technology, Ministry of Education, College of Chemistry, Sichuan University , Chengdu 610064, People's Republic of China.
Rui-Xiang
0000-0003-0756-3722
RX
Li