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Indian Journal of Chemistry -Section B (IJC-B) >
IJC-B Vol.44B [2005] >
IJC-B Vol.44B(09) [September 2005] >
| Title: | Vilsmeier-Haack reagent: A facile synthesis of 2-chloro-3-formylquinolines from N-arylacetamides and transformation into different functionalities |
| Authors: | Srivastava, Ambika
Singh, R M |
| Keywords: | Vilsmeier-Haack reagent
2-chloro-3-formylquinolines
N-arylacetamides |
| Issue Date: | Sep-2005 |
| Publisher: | CSIR |
| IPC Code: | Int.Cl.7 C 07 D 215/00 |
| Abstract: | A simple and regioselective synthesis of
2-chloro-3-formylquinolines through Vilsmeier-Haack cyclisation of
N-arylacetamides has been reported. The cyclisation is facilitated by N-arylacetamides
bearing electron donating groups at m-position.
However, yields of quinolines having electron donating groups are good in all
cases. Further, the nucleophilic substitution reaction of the quinolines is
also investigated. Similarly, the formyl group in the quinolines is subjected
to further transformation into cyano (CAN-NH3) and alkoxycarbonyl
(NIS-K2CO3/alcohols) groups to afford corresponding
3-cyano and 3-alkoxycarbonylquinolines, respectively. |
| Page(s): | 1868-1875 |
| ISSN: | 0975-0983(Online); 0376-4699(Print) |
| Source: | IJC-B Vol.44B(09) [September 2005]
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