The synthesis of semirigid analogs of PK 11195, the highly specific peripheral benzodiazepine-receptor ligand, is reported. Compound (4) underwent the Wittig reaction with acetaldehyde to give olefin (7) which after allylic bromination was aminated to give the omega-amino esters (10a-c). These compounds were then hydrogenated and cyclized in boiling toluene with DMAP as catalyst. The standard procedure failed in the case of compound (10b), thus other cyclization procedures were examinated.
Cappelli, A., Anzini, M., Vomero, S. (1994). Synthesis of 4-Substituted-1,2,3,4-tetrahydro-11-phenyl-5H-azepino[3,4-b]quinolin-5-one as Potential Peripheral Benzodiazepine-receptor Ligands. HETEROCYCLES, 38(6), 1265-1272 [10.3987/COM-93-6662].
Synthesis of 4-Substituted-1,2,3,4-tetrahydro-11-phenyl-5H-azepino[3,4-b]quinolin-5-one as Potential Peripheral Benzodiazepine-receptor Ligands
Cappelli, Andrea;Anzini, Maurizio;Vomero, Salvatore
1994-01-01
Abstract
The synthesis of semirigid analogs of PK 11195, the highly specific peripheral benzodiazepine-receptor ligand, is reported. Compound (4) underwent the Wittig reaction with acetaldehyde to give olefin (7) which after allylic bromination was aminated to give the omega-amino esters (10a-c). These compounds were then hydrogenated and cyclized in boiling toluene with DMAP as catalyst. The standard procedure failed in the case of compound (10b), thus other cyclization procedures were examinated.
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https://hdl.handle.net/11365/8108
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