Journal of the Chemical Society. Perkin transactions I p. 1671 - 1680 (1992)
Update date:2022-08-04
Topics:
Costa, Brian de
George, Clifford
Dominguez, Celia
Isomeric isothiocyanate derivatives 2-7 of the potent dopamine re-uptake (DA) inhibitor 1-<1-(2-benzothienyl)cyclohexyl>piperidine (BTCP 1) have been synthesized as potential irreversible ligands for this site.NaNO2-CF3CO2H provided a mild procedure for mononitration of the benzothienyl ring of 1 as a route to aryl isothiocyanates 5-7.Novel methodology, utilizing 3,3-ethylenedioxypentane-1,5-diol dimethanesulfonate ester is described for the synthesis of piperidone 13, a precursor for 4-isothiocyanatopiperidine 2.NaBH4 or LiAlH4 reduction of 4-(2-benzothienyl)-4-hydroxycyclohexanone 18 and 4-(2-benzothienyl)-4-(piperidino)cyclohexanone oxime 35 gives the corresponding cis-diol 21 and cis-cyclohexane-1,4-diamine 36 as the major isomers which have been investigated as precursors to the cyclohexane ring isothiocyanates 3 and 4.Alternative routes to 3 and 4 are compared and their stereochemical outcome investigated.
View MoreShanghai Hanshare Industry Co.,Ltd.
Contact:86 21 20960688
Address:RM902-903,Building E, Wanda Plaza,No.26,Zhoukang Road, Pudong District, Shanghai, China
website:http://www.fwdchem.com
Contact:86-21-54450828
Address:Room 802,Lotus Tower ,159 Tianzhou Road,Xuhui District,Shanghai
website:http://www.tbbmed.com
Contact:86--21-50498136
Address:Room 6002, Building 7-1, No.160 Basheng Road,Pudong Area,Shanghai China
NEW FORTUNE INDUSTRIAL CO.,LTD.
website:http://newfortune.lookchem.com/
Contact:+86-25-8645-9456
Address:C4-105 GREEN ISLAND FLOWER TOWN
Changde Yungang Biotechnology Co., Ltd
website:http://www.cdyg.com
Contact:+86-736-7391178
Address:Qiaonan Industrial Park, Changde City, Hunan Province
Doi:10.1039/d0tc05355d
(2021)Doi:10.1002/anie.201304654
(2013)Doi:10.1021/ja00978a035
(1967)Doi:10.1021/om400197j
(2013)Doi:10.1002/chem.201203216
(2012)Doi:10.1021/acs.orglett.9b02633
(2019)
