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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
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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