The reaction of tetralones with nitriles: a simple approach to the synthesis of new substituted benzo[h]quinazolines, benzo[f]quinazolines and dibenzo[a,i]phenanthridines

Autor:	Rachid Chatt, Roberto Martínez-Álvarez, Angel Martínez Sánchez, John Almy, Rachid Chioua, Mourad Chioua, Antonio Herrera
Rok vydání:	2006
Předmět:	chemistry.chemical_compound Nitrile chemistry Organic Chemistry Drug Discovery Organic chemistry General Medicine Biochemistry Medicinal chemistry Tetralones
Zdroj:	Tetrahedron. 62:2799-2811
ISSN:	0040-4020
DOI:	10.1016/j.tet.2006.01.010
Popis:	The one-pot reaction of 1-tetralone with nitriles in the presence of triflic anhydride affords in good yields 2,4-disubstituted 5,6-dihydrobenzo[ h ]quinazolines, which oxidation with DDQ leads to the corresponding benzo[ h ]quinazolines. 2-Tetralone undergoes identical process forming 1,3-disubstituted 5,6-dihydrobenzo[ f ]quinazolines. However, when the reaction of 2-tetralone is carried out with methylthiocyanate as nitrile, 5-methylthiotetrahydrodibenzo[ a , i ]phenanthridines are isolated in good yields. Easy transformations of the methylthio group offer possible access to a variety of substituted dibenzo[ a , i ]phenanthridines.
Databáze:	OpenAIRE
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