influence of n(2)-substitution in the alkylation of...

2005 Pyrazine derivatives R 0550 Influence of N(2)-Substitution in the Alkylation of (4S)-Alkyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-diones. — In the N(2)-substituted compounds, the stabilization of the lithium azaenolate caused by the phenyl substituent and the repulsive steric 1,2-interactions present in the 1,4-trans derivatives initially formed from starting compounds (XI) and (XIV), favor a C(1)-epimerization to the 1,4-cis iso- mers. — (HERNANDEZ, F.; MORALES, V.; BUENADICHA, F. L.; SOELLHUBER*, M.; AVENDANO, C.; Tetrahedron: Asymmetry 15 (2004) 19, 3045-pp; Dep. Quim. Org., Fac. Farm., Univ. Complutense, E-28040 Madrid, Spain; Eng.) — Klein 10- 160

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Page 1: Influence of N(2)-Substitution in the Alkylation of (4S)-Alkyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-diones

2005

Pyrazine derivativesR 0550 Influence of N(2)-Substitution in the Alkylation of (4S)-Alkyl-2,4-dihy-

dro-1H-pyrazino[2,1-b]quinazoline-3,6-diones. — In the N(2)-substituted com-pounds, the stabilization of the lithium azaenolate caused by the phenyl substituent and the repulsive steric 1,2-interactions present in the 1,4-trans derivatives initially formed from starting compounds (XI) and (XIV), favor a C(1)-epimerization to the 1,4-cis iso-mers. — (HERNANDEZ, F.; MORALES, V.; BUENADICHA, F. L.; SOELLHUBER*, M.; AVENDANO, C.; Tetrahedron: Asymmetry 15 (2004) 19, 3045-pp; Dep. Quim. Org., Fac. Farm., Univ. Complutense, E-28040 Madrid, Spain; Eng.) — Klein

10- 160

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