Journal of Organic Chemistry p. 4848 - 4853 (1984)
Update date:2022-08-04
Topics:
Schweizer, Edward E.
Lee, Kee-Jung
The direct LiAlH4 reduction of 2,3-dihydro-1H-imidazo<1,2-b>pyrazol-2-ones, 2, to 2,3-dihydro-1H-imidazo<1,2-b>pyrazoles, 10, was unsuccessful.When the amide 2 had an N-phenyl-substituent the reduction gave an N-carbonyl cleavage followed by carbonyl reduction to amino alcohols 6a-d.When the amide 2 had N-methyl, N-tert-butyl, or N-2,6-dimethylphenyl as a substituent, then cleavage yielded an unusual formamide product, 9e-i.Further LiAlH4 treatment of 9e-h gave 10e-h by reductive ring closure of the iminium zwitterion 11e-f, 14g, or 14h by addition of hydride to theintermediate 11g or 11h and/or carbonyl cleavage to 13e or 13f.LiAlH4 treatment of 9i gave only 13i.Dehydrative ring closure of compounds 6a and 6b with P2O5 gave the products 10a and 10b.
View MoreHANGZHOU YUNUO CHEMICAL CO.,LTD
website:http://www.yunuochem.com
Contact:0571-83715115
Address:hangzhou
SHAANXI TOP PHARM CHEMICAL CO.LTD
Contact:+86-029-85733403
Address:No.108 ,west sector,south er huan,xi'an,china
Suzhou Time-chem Technologies Co., Ltd.
Contact:0512-63983931/68086856
Address:No. 1326 of Binhe Road, New District, Suzhou, Jiangsu, P. R. China
Contact:+86-532-80762375
Address:No. 6, Hongkong Middle Road, Qingdao, China
Chengdu Green technology Co.,Ltd.
Contact:86-28-82608355
Address:C9 ,Economic Headquarters, Economic Development Zone, Chengdu.
Doi:10.1021/jm50001a004
(1985)Doi:10.1021/jp803119j
(2008)Doi:10.1016/S0020-1693(00)93736-8
(1985)Doi:10.1039/P29840001851
(1984)Doi:10.1021/jo00213a006
(1985)Doi:10.1016/0022-328X(84)80079-0
(1984)