A new stereocontrolled approach to fused polycyclic compounds containing a diketopiperazine ring |
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| Institution: | 1. Museo Geominero, Instituto Geológico y Minero de España - IGME, Ríos Rosas 23, Madrid E-20003, Spain;2. Departamento de Sistemas y Recursos Naturales, E.T.S. de Ingeniería de Montes, Forestal y del Medio Natural, Universidad Politécnica de Madrid, 28040, Madrid, Spain;3. CGG Services (UK) Ltd., Llandudno, North Wales LL30 1 SA, UK |
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| Abstract: | Representative (1S)- and (4S)-alkyl-1,4-dihydropyrazino2,1-b]quinazoline-3,6-dione lactim ethers were regio- and diastereoselectively alkylated after metallation to give the corresponding 1,4-trans-isomers with retention of the stereocentres. The results were compared with the previously studied lactams. The (1R,4S)-dialkyl derivatives obtained by C(1)-alkyation with bifunctional reagents were lately cyclized to complex polycyclic compounds through a second N(2)-alkylation promoted by sodium iodide. |
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