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ChemInform Abstract: A Concise Synthesis of Fluorine-Containing Benzo[h]quinolines and Benzo[h]quinolones by Selective Pyridine and Pyridinone Rings Formation Reactions of N-Propargyl-2,4-bis(trifluoroacetyl)-1-naphthylamine with Various Active Methylene
- Source :
- ChemInform. 41
- Publication Year :
- 2010
- Publisher :
- Wiley, 2010.
-
Abstract
- N-Propargyl-2,4-bis(trifluoroacetyl)-1-naphthylamine (3) underwent nitrogen-containing heterocyclic ring-formation reactions with a variety of active methylene compounds in the presence of sodium alkoxides. This annulation reactions with dialkyl malonates were highly dependent on reaction temperature to give selectively the corresponding fluorine-containing benzo[h]quinolines (5) at high temperature and 1H-benzo[h]quinolin-2-ones (7 and 8) at low temperature. Furthermore, changing the electron-withdrawing groups of active methylene compounds led to alternation of the reactive site wherein the reagents attack first and to the formation of the different nitrogen-containing heterocyclic systems, pyridine (9), dihydropyridine (11 and 13) and pyridone (12).
Details
- ISSN :
- 15222667 and 09317597
- Volume :
- 41
- Database :
- OpenAIRE
- Journal :
- ChemInform
- Accession number :
- edsair.doi...........5b2a59a59c06b1eebacc946e2305a94c