Synthesis of tetrahydro-1,4-benzodiazepine-2-ones on hydrophilic polyamide SynPhase lanterns.
Solid-phase synthesis is greatly dependent on the solid support. Here, we report the use of a new hydrophilic grafted surface on SynPhase lanterns in solid-phase organic chemistry. A convenient and facile solid-phase synthesis of disubstituted 1,4-benzodiazepine-2-ones on polyamide SynPhase lanterns is described. The key step of the synthesis involved a reduction-cyclization of a nitroaryl methyl ester with a mixture of tin(II) chloride dihydrate and ammonium acetate in water and ethanol at elevated temperature to give the desired target compounds. A library of 21 disubstituted 1,4-benzodiazepine-2-ones was prepared.
Wu
Zemin
Z
Mimotopes Pty Ltd, 11 Duerdin Street, Clayton, Victoria 3168 Australia.
Ercole
Francesca
F
FitzGerald
Michael
M
Perera
Senake
S
Riley
Phil
P
Campbell
Rhonda
R
Pham
Yen
Y
Rea
Philip
P
Sandanayake
Saman
S
Mathieu
Marc N
MN
Bray
Andrew M
AM
Ede
Nicholas J
NJ
D001570:Benzodiazepinones / Q000138:chemical synthesis*; D002851:Chromatography, High Pressure Liquid; D007202:Indicators and Reagents; D009757:Nylons / Q000138:chemical synthesis* / Q000737:chemistry; D011137:Polystyrenes / Q000737:chemistry
D001570:Benzodiazepinones; D007202:Indicators and Reagents; D009757:Nylons; D011137:Polystyrenes