(4S)-2,4-Dimethyl-2,4-dihydro-3,6-dioxo-(1H)-pyrazino[2,1-b]quinazolyl tosylate as an electrophilic glycine template

Article abstract of DOI:10.1016/S0040-4020(98)01188-0

(4S)-2,4-Dimethyl-2,4-dihydro-(1H)-pyrazino[2,1-b]quinazoline-3,6-dione was converted into to the cis-tosylate 2, whose reactivity as an electrophilic glycine template is discussed. It was found that this compound does not give direct S(N)2-type displacement of the tosyloxy group. However, the 1-hydoxy derivative 3, obtained by hydrolysis of 2 with net retention of the stereochemistry, and its 1-methoxy derivative 4a are electrophilic glycine templates.