- A convenient one-pot synthesis of thiazol-2-imines: application in the construction of pifithrin analogues
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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 pKas 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.
- Murru, Siva,Singh,Kavala, Veerababurao,Patel, Bhisma K.
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p. 1931 - 1942
(2008/09/17)
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- Synthesis and Mercuration of Some New 3-Aryl-2-arylimino-4,5-disubstituted-δ4-thiazolines and Their Fungicidal and Bactericidal Activities
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A series of new 3-aryl-2-arylimino-4,5-disubstituted-Δ4-thiazolines (I) have been synthesised by condensing various ketones having active methylene group with sym-diarylthioureas in the presence of bromine.The thiazolines (I) on mercuration with one equivalent of mercuric acetate in acetic acid give 3-(acetoxymercuriaryl)-2-arylimino-4,5-disubstituted-Δ4-thiazolines (II).All the compounds have been assayed against the fungus Pyricularia oryzae (Cav) and the bacteria Esch. coli and Staph. aureus, and the structure-activity relationship has been discussed.
- Mohanty, J.,Mahapatra, G. N.
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