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Paper | Regular issue | Vol 34, No. 4, 1992, pp.771-780
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5962
The Synthesis of Spirocyclic [1,2,4]Triazolo[4,3-a]quinolines as Potential Ligands for the Benzodiazepine Receptor

Lawrence A. Reiter* and Gary E. Berg

*Central Research Division, Pfizer Inc, Groton, CT 06340, U.S.A.

Abstract

Two spirocyclic [1,2,4]triazolo[4,3-a]quinolines (1a and b) have been prepared as potential ligands for the benzodiazepine receptor. Both compounds were prepared using the strategy of doubly deprotonating an acetanilide derivative followed by reaction with α-tetralone. The resulting alcohols were converted to the corresponding spirocyclic 3,4-dihydroquinolin-2-one or -2-thione by treatment with neat HF. Triazole formation was effected by standard procedures. An alternate strategy starting with an intact triazole was unsuccessful but this route led to the first example of a lateral metallation of a 4-substituted 1,2,4-triazole.