Synthesis and properties of deoxypegan-1-one

Quinazolyl-2-propionic acid hydrochloride (5) was synthesized by reduction of N-(o-nitrobenzyl)succinimide with tin chloride. A pyrroloquinazolin-1-one {4, 3,9-dihydropyrrolo[2,1-b]quinazolin-1(2H)-one} was prepared in 68% yield by heating 5 in Ac₂O and subsequent treatment with Et₃N. Compound 4 was obtained in 71% yield in one step by reduction of N-(o-nitrobenzyl)succinimide with Fe in the presence of HCl. Compound 4 was protonated, alkylated, and acylated on the N₍₄₎ atom. Derivatives of quinazolyl-2-propionic acid and 1-(2-aminobenzyl)succinimide were prepared by reaction of derivatives of 4 with nucleophilic reagents. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 459–462, September–October, 2006.