Journal of Organic Chemistry p. 5927 - 5929 (1988)
Update date:2022-08-02
Topics:
Krapcho, A. Paul
Avery, Kenneth L.
The displacements of 1-halo- and 1,4-dihaloanthracene-9,10-diones by N,N-disubstituted hydrazines have been studied.These reactions proceed via N-N bond cleavages of the hydrazine to yield products with the regiospecific incorporation of an N,N-disubstituted amino group.In addition, pyrazoles which arise from intermediates which undergo N-C bond cleavage are also formed.The ratio of the N-N to N-C cleavage products is dependent on the reaction solvent, temperature, structure of the hydrazine, and the nature of the leaving group being displaced from the anthracene-9,10-dione.For example, treatment of 1a with N,N-dimethylhydrazine in pyridine or dimethyl sulfoxide (DMSO) leads to 3a:2c ratios of 6 and 3, respectively.Compound 1e under comparable reaction conditions gives 3a:2c product ratios of 49 and 4, respectively.The dichloro dione 1c with N,N-dimethylhydrazine in pyridine or DMSO leads predominantly to 3b in 76percent and 72percent yields, respectively, with relatively little pyrazole 2d.The more reactive difluoro dione 1h on reaction with N,N-dimethylhydrazine in pyridine leads to N-N bond-cleavage products 3c (48percent) and 3d (40percent).Treatment of 1e with 1-piperidinamine in pyridine yields 3f.The results will be discussed.
View MoreTaimai Sanluck Pharmaceutical Co.,Ltd
Contact:86-592-7662921
Address:8D,No.186,Huarong Road,Huli,Xiamen,China
Contact:0027-717-456976
Address:2ND FLOOR, 325 VAUSE ROAD, OVERPORT, 4001, SOUTH AFRICA
Hangzhou Mole's Science & Technology Co.,Ltd.
Contact:+86-571-56880228
Address:15F Guodu development Building, NO.182 Zhaohui Road
Dongtai Xinyuan Chemical Co., Ltd.
Contact:+86-21-56733000
Address:404F, 99Nong No.117 Zhongtan Rd. Shanghai
Tianjin Puck Rice Chemicals Co., Ltd.
Contact:022-58054572
Address:Weidi Road
Doi:10.1021/jm900519b
(2009)Doi:10.1016/S0040-4039(00)80070-2
(1988)Doi:10.1016/j.tetlet.2009.05.028
(2009)Doi:10.1016/S0040-4039(00)96875-8
(1987)Doi:10.1055/s-0032-1317379
(2012)Doi:10.1021/ja9039407
(2009)