Journal of Organic Chemistry p. 3665 - 3668 (1982)
Update date:2022-08-05
Topics:
Yuste, Francisco
Sanchez-Obregon, Ruben
The base-catalyzed reaction of hydroxy lactone 1 with several cyclic and acyclic vinylogous amides and 1,3-dicarbonyl compounds was found to provide a smooth method to prepare pyrrole, furan, tetrahydroindole, and tetrahydrobenzofuran ring systems.The reaction of 1 with the cyclic enaminone 2 affords 3 which can be isomerized to the tetrahydroindole-2-acetic acid 4.The reaction of 1 with 6 and 8 produces, after esterification, the methyl tetrahydroindole-and pyrrole-2-acetates 7a and 9a, respestively.With acyclic 1,3-dicarbonyl compounds, 1 reacts to give furan-2-acetic acids, whereas the reaction of 1 with cyclic β-diketones leads to furo<3,2-b>benzofuran derivatives.The latter can be easily isomerized by heating with diluted acid to the corresponding tetrahydrobenzofuran-2-acetic acids.A possible mechanism for these reactions is proposed.
View MoreGuangzhou PI & PI Biotech Inc. Ltd.
Contact:+86-20-81716320
Address:Suite 501,198 Kaiyuan Ave.,Science City, Guangzhou,China
ALPHA PHARMACEUTICAL CO,LTD JIANGSU
Contact:+86-527-84829968,+86-527-84829998
Address:suqian city
website:http://www.acrospharmatech.com
Contact:+1-3234804688
Address:Flat/RM 1502,Easey Commercial building 253-261 Hennessy Road,Wanchai,HongKong
Contact:+86-838-5655598
Address:Guanghan Nanfeng Industrial Zone
Contact:0086-29-89196322
Address:North of the Fifth Keji Road, Hi-Tech Industrial Zone, Xi'an City, Shaanxi Province, China
Doi:10.1016/S0008-6215(82)80027-X
(1982)Doi:10.1021/ja00384a068
(1982)Doi:10.1080/07328309908543993
(1999)Doi:10.1021/ol0513903
(2005)Doi:10.1039/DT9820001019
(1982)Doi:10.1139/v65-430
(1965)