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http://nopr.niscpr.res.in/handle/123456789/16734| Title: | Synthesis of 4-(N,N-dimethylaminomethylene)-2-alkyl-2-oxazolin-5-ones via Vilsmeier Haack reagent and their reactions with various N- and O-nucleophiles |
| Authors: | Singh, Ram S Singh, Radhey M |
| Issue Date: | Sep-2000 |
| Publisher: | NISCAIR-CSIR, India |
| Abstract: | The 4-N,N-dimethylaminomethylene)-2-alkyl-2-oxazolin-5-ones 4 have been synthesised from N-acyl-α-amino acids 2 and methyl esters 3 with Vilsmeier-Haack reagent. The reaction of oxazolones 4a,c with primary alkylamines 7 in acetonitrile takes place at exocyclic olefinic carbon to afford substituted product 4-alkylaminomethylene-2-alkyl-2-oxazolin-5-ones 8, whereas the reaction of oxazolones 4a-d with hydrazinc hydrate gives cyclised product 4-acylamino-5 -hydroxypyrazoles 9a-d, respectively. The methanolysis of oxazolones 4c,d with sodium methoxide in methanol takes place at lactone carbonyl carbon to give methyl 2-acylamino-3-dimethylaminopropenoates 12c,d. However, the ethanolysis with sodium ethoxide in ethanol occurrs at exocyclic carbon to afford 4-hydroxymethylene-2-oxazolin-5-ones 14c,d and N-acyl-α-amino acids 15c,d at room and reflux temperature, respectively. |
| Page(s): | 688-693 |
| ISSN: | 0975-0983(Online); 0376-4699(Print) |
| Appears in Collections: | IJC-B Vol.39B(09) [September 2000] |
Files in This Item:
| File | Description | Size | Format | |
|---|---|---|---|---|
| IJCB 39B(9) 688-693.pdf | 1.39 MB | Adobe PDF | View/Open |
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