Journal of Organic Chemistry p. 2127 - 2134 (1992)
Update date:2022-08-05
Topics:
Becher, Jan
Joergensen, Per Lauge
Pluta, Krystian
Krake, Niels J.
Faelt-Hansen, Birgitte
5-Chloro-1-methylpyrazole-4-carboxaldehydes 1 react with excess sodium azide in dimethyl sulfoxide to produce a mixture of 1-azidomethyl-4-cyanopyrazoles 2 and 4-cyano-5-hydroxy-1-methylpyrazoles 3.Application of this reaction to the corresponding 5-chloro-1-phenylpyrazole-4-carboxaldehydes 5 gave 4-cyano-5-hydroxy-1-phenyl-pyrazoles 7 as the sole products in high yields.Likewise, 2-aryl-5-chloro-1-methylpyrrole-3,4-dicarboxaldehydes 9 rearranged to 2-aryl-4-cyano-5-hydroxy-1-methylpyrrole-3-carboxaldehydes 10 in high yields.In the indole series, treatment of 1-aryl-2-chloroindole-3-carboxaldehydes 11 with NaN3 yielded a mixture of 1-aryl-3-cyano-2(3H)-indolones 13 and 1-aryl-5-azido-3-cyanoindoles 12, both products resulting from a ring-opening-ring-closure reaction with concomitant nucleophilic tele-substitution at the 5-position of the indole ring.
View MoreVanderArk International Limited
Contact:86-10-82437576
Address:Qing He
Jewim Pharmaceutical (Shandong) Co., Ltd
Contact:+8615621883869
Address:山东省泰安市高新技术产业开发区配天门大街西首
Nanjing Chemical Material Corp.(NCMC)
website:http://www.njchemm.com
Contact:0086-25-83172879
Address:B12 Technology and Innovation Building, Nanjing Tech University, No.5 New Model Road
ShangHai Original Economy-Trade Develop Co.,Ltd.,
Contact:86-21-68552131
Address:shanghai
HEZE KINGVOLT CHEMICAL CO., LTD
Contact:86-573-82118911
Address:Juancheng Industry Park
Doi:10.1021/jo301025k
(2012)Doi:10.1016/S0040-4039(00)78266-9
(1994)Doi:10.1248/cpb.39.2863
(1991)Doi:10.1016/0040-4039(91)80418-6
(1991)Doi:10.1021/acs.joc.8b01450
(2018)Doi:10.1021/jm301000k
(2012)