Journal of the Chemical Society. Perkin transactions I p. 1607 - 1613 (1980)
Update date:2022-08-05
Topics:
Kametani, Tetsuji
Kigawa, Yoshio
Nemoto, Hideo
Ihara, Masataka
Fukumoto, Keiichiro
Condensation of pyrrolidine-2-thione (21) with methyl α-bromo-(2-bromo-4,5-dimethoxyphenyl)acetate (15) gave methyl (Z)-α-(2-bromo-4,5-dimethoxyphenyl)-α-pyrrolidin-2-ylideneacetate (25) in high yield.Several other methyl (Z)-α-aryl-α-<3-acetoxy-4-(N-ethoxycarbonyl-N-methylamino)pyrrolidin-2-ylidene>acetates (26)-(31) were also synthesised in good yields from reaction of the corresponding phenylacetates (15), (12), and (13) with trans-3-acetoxy-4-(N-ethoxycarbonyl-N-methylamino)pyrrolidine-2-thione (20).Treatment of compounds (25)-(31) with sodium hydride and copper(I) bromide in dimethylformamide afforded methyl 2,3-dihydro-6,7-dimethoxy-1H-pyrrolo<1,2-a>indole-9-carboxylate (34) and the methyl (+/-)-trans-1-acetoxy-2-(N-ethoxycarbonyl-N-methylamino)-2,3-dihydro-1H-pyrrolo<1,2-a>indole-9-carboxylates (35)-(37) in good yields.Methyl (+/-)-trans-1-acethoxy-2-(N-ethoxycarbonyl-N-methylamino)-2,3-dihydro-7-methoxy-6-methyl-1H-pyrrolo<1,2-a>indole-9-carboxylate (36) was converted into the 5,8-quinone (3), via the 8-nitro-compound (38).
View MoreContact:+36(21)2523420
Address:Head office: 1102 Budapest, SZENT LASZLO TER 24/B. 1/1., HUNGARY / CHINA
Contact:(86) 731 88718666
Address:Room 1222, Unit 4, Building B, Shangcheng, No.47, Kaiyuan East Road.
Contact:+86-18200374913
Address:Hongmei Road, No. 99
Changzhou Sunlight Pharmaceutical Co., Ltd.
Contact:+86-519-83131668;83139028;83138042;83137041
Address:JiuliStreet, Benniu Town Changzhou City, Jiangsu Province
Hangzhou J&H Chemical Co., Ltd.
website:http://www.jhechem.com/
Contact:+86-571-87396432
Address:No.200 Zhenhua Rd.Xihu Industrial Park, Hangzhou 310030, China
Doi:10.1039/j39710001527
(1971)Doi:10.1021/jm050588q
(2006)Doi:10.1016/S0960-894X(99)00181-X
(1999)Doi:10.1016/j.bmcl.2009.06.094
(2009)Doi:10.1002/cmdc.201402033
(2014)Doi:10.1021/jm000300r
(2000)
