ALKYLATION AND REDUCTION REACTIONS IN THE ISOQUINOQUINAZOLINE SERIES

Article abstract of DOI:10.1007/BF00474239

Protonation and methylation of 5-oxo-7,12-dihydro-5H-isoquino<2,3-a>quinazoline occur at the N₍₆₎ atom, while methylation of 5-oxo- and 6-methyl-5-oxo-6,6a,7,12-tetrahydro-5H-isoquino<2,3-a>quinazolines takes place at the N₍₁₃₎ atom; the degree of stereoselectivity varies depending on the presence of a substituent attached to N₍₁₃₎.Based on PMR spectral analysis utilizing the nuclear Overhauser effect, we have established the structure and studied the conformational behavior of the tosylate derivatives of cis-13-methyl-, trans-13-methyl-, and cis-6,13-dimethyl-5-oxo-6,6a,7,12-tetrahydro-5H-isoquino<2,3-a>quinazolinium ions.