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http://nopr.niscpr.res.in/handle/123456789/16240| Title: | An unusual resistance to  -bromination by arylacetyl compound. Studies on bromination of 2-acetylbenzimidazoles and their subsequent reactions with sulphur nucleophiles - synthesis of novel β-ketosulphone derivtives of benzimidazoles. |
| Authors: | Ramaiah, K Dubey, P K Ramanatham, J |
| Issue Date: | Mar-1999 |
| Publisher: | NISCAIR-CSIR, India |
| Abstract: | Condensation
of o -phenylenediamine with lactic
acid under Phillips ' conditions gave the known 2- (-hydroxyethyl)benzimidazole 1 which on oxidation with acid
dichromate furnishes 2-acetylbenzimidazole 2.
Reaction of 2 with bromine in acetic
acid at room temp. give a novel product 3 but not the expected 2-(-bromoacetyl
benzimidazole 4. Rational
explanation is offered for this anamolous behaviour of 2. Compound 2 on
alkylation, give 1-alkyl derivatives which undergo smooth bromination with
bromine in acetic acid to give the correspondig 1-alkyl-2- (-bromoacetyl) benzimidazoles.
Reactions of latter with sulphur nucleophiles such as PhS-, ArSO2- etc.
, resulting in substitution of bromine, leading to novel -β ketosulphone derivatives of benzimidazoles, are
reported. Products have been characterised by IR , NMR (1H and 13C)
and mass spectral data. |
| Page(s): | 302-307 |
| Appears in Collections: | IJC-B Vol.38B(03) [March 1999] |
Files in This Item:
| File | Description | Size | Format | |
|---|---|---|---|---|
| IJCB 38B(3) 302-307.pdf | 1.29 MB | Adobe PDF | View/Open |
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