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 MoreContact:+86-21-6856-1349 523-87676172
Address:No16 . BinJiang Road . Taixing Economy Developing Area .JiangSu Province . China
Shanghai Mintchem Development ., Ltd
Contact:0086 21 5190 8570
Address:R602,4#,89Nong, Mudan Road Pudong Shanghai China
Xi'an Costrong Pharmaceutical Co., Ltd.
Contact:029- 68576496
Address:Room 2004,Shuibao Building,No.190,South Erhuan Rd, Yanta District,Xi'an,Shaan Xi,China
Contact:86-510-82853889
Address:Rm.3732, No.18-2,Yonghe Rd.,Wuxi,Jiangsu,214023,China
Jiangxi Huashi Pharmaceutical Co., Ltd
Contact:+86-795-4509628
Address:No.199, Ningbo Avenue, Fengxin industrial park, Fengxin county, Yichun city, Jiangxi
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)
