Journal of the Chemical Society. Perkin transactions I p. 691 - 696 (1988)
Update date:2022-08-06
Topics:
McFarlane, Michael D.
Moody, David J.
Smith, David M.
Cyclisation of N-(4- or 5-acylamino-2-nitrophenyl)glycine esters in basic media gives alkyl 5- or 6-acylaminobenzimidazole-2-carboxylate N-oxides, e.g. (11a) or (11b).Acid hydrolysis of the latter, followed by the reaction of ammonia, gives the title compounds (1b) and (1c), in acceptable yield.The corresponding reaction sequence with 4-acylamino-N-cyanomethyl-o-nitroanilines also gives (1b); where the acyl group is methylsulphonyl, however, the final product is 5-methanesulphonamidobenzimidazole N-oxide (9).Compound (1b) is also obtainable from ethyl 5-nitrobenzimidazole-2-carboxylate N-oxide by reduction followed by hydrolysis.Attempts to cyclise N-(o-nitrophenyl)glycine derivatives containing a free amino group at the 5-position are unsuccessful.This failure is attributed to mesomeric deactivation of the nitro group by the amino lone pair.
View Morewebsite:http://www.antimex.com
Contact:0086-21-50563169
Address:Room1027,No.Jinyu Road,Pudong
FOSHAN NANHAI ZHONGNAN PHARMACEUTICAL FACTORY
Contact:0086-0757-85609331
Address:XIAHENGTIAN INDUSTRIAL ZONE,SHAYONG VILLAGE,LISHUI TOWN
Cangzhou Senary Chemical Science-tech Co., Ltd
Contact:+86-317-3563899, 3563699
Address:168 Jinde Road, Cangzhou, Hebei, China
HANGZHOU YUNUO CHEMICAL CO.,LTD
website:http://www.yunuochem.com
Contact:0571-83715115
Address:hangzhou
Contact:+86-0512-62857507
Address:Boji Science Park, No1688C,Taishan road, Suzhou ,China
Doi:10.1016/S0040-4039(00)00337-3
(2000)Doi:10.1007/BF00938733
(1980)Doi:10.1021/jo00151a022
(1983)Doi:10.1016/0008-6215(95)00021-K
(1995)Doi:10.1016/0040-4039(80)80213-9
(1980)Doi:10.1021/ja00393a050
(1981)
