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A convenient one-pot synthesis of thiazol-2-imines: application in the construction of pifithrin analogues
- Source :
-
Tetrahedron . Feb2008, Vol. 64 Issue 8, p1931-1942. 12p. - Publication Year :
- 2008
-
Abstract
- Abstract: For the first time a reaction intermediate has been isolated giving further insight into the mechanism of thiazol-2-imine formation. The first step of the reaction requires a basic medium, while the second step is an acid mediated E1 elimination reaction. An efficient one-pot synthesis of substituted thiazol-2-imines have been achieved by the condensation of carbonyl compounds with thioureas and 1,3-disubstituted thioureas using 1,1′-(ethane-1,2-diyl)dipyridinium bistribromide (EDPBT). Unsymmetrical 1,3-disubstituted thioureas give regioselective products with symmetrical ketones, which are mainly governed by the pK as of NH protons of thiourea, whereas symmetrical 1,3-disubstituted thioureas give regioselective products with symmetrical carbonyl compounds owing to the regioselective bromination of ketones. The methodology is extended to access novel neurodegenerative drug candidate pifithrin-α analogues in good yields in shorter reaction time. This method is simple, versatile and is applicable for different 1,3-disubstituted thioureas as well as a range of carbonyl compounds. [Copyright &y& Elsevier]
- Subjects :
- *IMINES
*ORGANONITROGEN compounds
*IMINO compounds
*KETONES
Subjects
Details
- Language :
- English
- ISSN :
- 00404020
- Volume :
- 64
- Issue :
- 8
- Database :
- Academic Search Index
- Journal :
- Tetrahedron
- Publication Type :
- Academic Journal
- Accession number :
- 28609209
- Full Text :
- https://doi.org/10.1016/j.tet.2007.11.076