A new route toward 4-substituted pyrazino[2,1-b]quinazoline-3,6-dione systems. Total synthesis of glyantrypine.
Treatment of sodium N-(o-azidobenzoyl)aminoacylglycinates 8 with acetic anhydride afforded 1-acetyl-4-(o-azidobenzoyl)-2,5-piperazinediones 7, with complete retention of the stereochemistry. The intramolecular aza Wittig reactions of compounds 7 in the presence of tributylphosphine followed by deacetylation gave 1,2-unsubstituted pyrazino[2,1-b]quinazoline-3,6-diones 1. This route was adapted to the synthesis of both enantiomers of the alkaloid glyantrypine.
Cledera
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P
Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, Madrid, Spain.
Avendaño
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C
Menéndez
J C
JC
D018432:Drug Resistance, Multiple; D009682:Magnetic Resonance Spectroscopy; D011799:Quinazolines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014364:Tryptophan / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D011799:Quinazolines; C075514:glyantrypine; D014364:Tryptophan