Tetrahedron p. 2653 - 2660 (1974)
Update date:2022-08-02
Topics:
Oikawa
Yonemitsu
On heating with trichloroacetic acid or trifluoroacetic acid, 2,4-dimethoxyphenethyl methylsulfinylmethyl ketone (1) cyclized to 2,3-dimethoxy-5-methylthio-6-oxo-5, 6, 7, 8-tetrahydronaphthalene (2) through an intramolecular nucleophilic substitution of a sulfonium ion intermediate (20b), while a β -ketosulfoxide having naphthalene nucleus (3) cyclized to a tetrahydrophenanthrene 4 via a Pummerer rearrangement product 23. Treatment of 1 with p-toluenesulfonic acid gave a mixture of 2,3,6-trisubstituted naphthalenes (7-10), whose composition was dependent on the reaction conditions. The aromatization proceeded via 2.
View Morewebsite:http://www.orchid-chem.com
Contact:+86-571-85395792
Address:607, North Zhongshan Road, Hangzhou 310000 China
Contact:86-511-85210668 0511-85210668, 85210818, 85210898
Address:Yihai Garden E-902,NO.99 Daxi RD., Zhenjiang Jiiangsu ,China
Contact:86-532-68629711 13780605697
Address:NO 220 YANAN 3 ROAD,(POST ADMINISTRATION BUILDING),QINGDAO,CHINA
Contact:+86-535-8888888
Address:No.161 Haishi Rd.
Zhengzhou Minzhong Pharmaceutical Co.,ltd
Contact:0086-371-65797115
Address:15/F,Jiangshan Bldg, NO.126 Huanghe Road,Zhengzhou, China
Doi:10.1021/jm00172a035
(1990)Doi:10.1016/j.tetlet.2020.151805
(2020)Doi:10.1021/om301031e
(2013)Doi:10.1016/j.tet.2012.06.076
(2012)Doi:10.1021/ol302950w
(2012)Doi:10.1016/j.bmcl.2012.09.074
(2012)
