Journal of Organic Chemistry p. 5451 - 5457 (1985)
Update date:2022-09-26
Topics:
Ketcha, Daniel M.
Gribble, Gordon W.
A Friedel-Crafts acylation of 1-(phenylsulfonyl)indoles (1) with carboxylic acid anhydrides and acid chlorides in the presence of aluminum chloride gives 3-acyl-1-(phenylsulfonyl)indoles (2) in 81-99percent yields.Base hydrolysis converts 2 to 3-acylindoles (3) in 79-96percent yields.The reaction of 1-(phenylsulfonyl)indole (1a) with oxalyl chloride gives acid chloride 2h, which is converted to 3-cyanoindole (7) in three steps (75percent yield).Although a similar Friedel-Crafts alkylation of 1 was unsuccessful, in some cases the 3-acyl-1-(phenylsulfonyl)indoles 2a,e,f could be reduced to 3-alkyl-1-(phenylsulfonyl)indoles 8a,b,c in nearly quantitative yield with sodium borohydride in trifluoroacetic acid.The acid chloride derived from keto acid 9 did not cyclize to the desired pyridocarbazole-5,11-quinone 24 but rather to chloro keto lactam 10.However, acylation of 1a with acid chloride 22 followed by strong-base-mediated cyclization gives 24.Since quinone 24 has been previously converted to the alkaloid ellipticine 26, this route to 24 represents a new synthesis of ellipticine.Related synthetic schemes give rise to quinones 16 and 20.
View MoreChongqing Rong&Quan Pharmaceutical Technology Co. , Ltd.
Contact:86-023-65268721
Address:No. 7, Manshanhong Village, Pingdingshan, Shapingba District, Chongqing Province, China
Yancheng Smiling Imp & Exp Co., Ltd.
Contact:+86-515-83173586
Address:Rm1207, BLD#03, Phoenix Plaza, Juheng Road, Yancheng, Jiangsu, P.R. China
JIAXING SUNS INTERNATIONAL TRADE CO LTD
Contact:18367306858
Address:No.123,Huixin Avenue,Huimin Dist
Shandong Yuanli Science and Technology Co., Ltd.
Contact:86-0536-6777557
Address:Zhuliu Industiral Park,Changle County
website:http://www.lonwinchem.com
Contact:Tel: 86-21-59858395
Address:No#966,Huaxu Road,Shanghai 201702,P.R.China
Doi:10.1016/S0040-4039(00)94940-2
(1985)Doi:10.1107/S0108270106050360
(2007)Doi:10.1016/S0040-4020(01)96883-8
(1984)Doi:10.1016/j.bmcl.2016.10.036
(2016)Doi:10.1021/jo01071a608
(1960)Doi:10.1007/BF00758625
(1987)