Kommi, Damodara N. ; Kumar, Dinesh ; Seth, Kapileswar ; Chakraborti, Asit K. (2013) Protecting group-free concise synthesis of (RS)/(S)-lubeluzole Organic Letters, 15 (6). pp. 1158-1161. ISSN 1523-7060
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Official URL: http://pubs.acs.org/doi/abs/10.1021/ol302601b
Related URL: http://dx.doi.org/10.1021/ol302601b
Abstract
Three new, concise, and protecting group-free synthetic routes for (RS)- and (S)-lubeluzole are reported in higher (46–62%) overall yields compared to the reported procedures (6–35%). The key steps involve C–N bond formation via epoxide aminolysis and nucleophilic substitution of 2-chlorobenzothiazole with suitably designed precursor amines and are performed in aqueous medium. Water offers an advantage in promoting the reactions compared to organic solvents and its role is envisaged as hydrogen-bond mediated electrophile–nucleophile dual activation.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 100268 |
| Deposited On: | 20 Jan 2017 09:19 |
| Last Modified: | 20 Jan 2017 09:19 |
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