Journal of Organic Chemistry p. 4362 - 4368 (1985)
Update date:2022-07-29
Topics:
Carpenter, Andrew J.
Chadwick, Derek J.
The effects of change of solvent, metalating agent, reaction time, and reaction temperature on the lithiation of N,N-diethylthiophene-2-carboxamide and of the N-tert-butyl-2-carboxamide derivatives of furan, thiophene, and 1-methylpyrrole are explored, and optimum conditions are established for ring β-directed metalation.The tertiary carboxamido group is less effective in this context than the secondary amide function and appears to be of limited value in these heteroaromatic systems.The high metalation levels achievable with the furan and thiophene secondary amides allow high-yielding syntheses (through reaction of the lithiated intermediates with a wide range of electrophiles) of otherwise inaccessible 2,3-disubstituted derivatives.The synthetical value of the methodology appears to be limited only by the forcing conditions required for amide hydrolysis.
View MoreChangzhou LanXu Chemical Co.,ltd.
Contact:86-0519-86330911,13656129734,15261186386
Address:Room 524, Depart.Chemical, Changzhou Science and Eductaion town, Jiangsu, China;Factory: Haian Fine Chemical Industry Park,Nantong,Jiangsu,China
Suzhou CarbonWell Pharma-Tech Co., Ltd
Contact:Tel: + 86 (0)512-8898-1216; + 86-18606258602
Address:2358 Changan Road, Wujiang Scientific Innovation Park, Wujiang, Jiangsu Province, P. R. China 215200
Zhengzhou Institute of Chiral Pharmer Research Co., Ltd.
Contact:86-371-55219111
Address:15 Floor, 2 Building, Central China Technovalley, Zhongyuan West Road
Taizhou YOJOY Chemical Co., Ltd.
Contact:13857143241
Address:Yangfu Industrial Park, Xianju, Zhejiang, P. R. China
Chemsigma International Co.,Ltd.
website:http://www.chemsigma.com
Contact:86-025-58748998
Address:Rm.705, 15th Building,Rd.Xinke II
Doi:10.1021/ja002395s
(2000)Doi:10.1016/S0022-328X(00)92479-3
(1975)Doi:10.1246/cl.1996.291
(1996)Doi:10.1007/BF00798282
(1985)Doi:10.1002/jhet.989
(2012)Doi:10.1002/hlca.19850680514
(1985)