62062-75-3Relevant articles and documents
Nitrogen Bridgehead Compounds. Part 35. Structures of α-Formyl-2,3-polymethylene-3,4-dihydroquinazolin-4-ones
Horvath, Agnes,Hermecz, Istvan,Pongor-Csakvari, Marianna,Meszaros, Zoltan,Koekoesi, Jozsef,et al.
, p. 219 - 224 (2007/10/02)
The structures of the title compounds bearing a five-, six- or seven-membered A ring have been investigated by uv and 1H and 13C nmr spectroscopy.The imine-enol-enamine (I-II-III) tautomerism of these compounds depends greatly on the ring size.A significant solvent-dependence is observed only for the five-membered-ring compounds 1 and 2, which in ethanolic solution exist predominantly in the imine form I, and in chloroform solution in the enol form II.The compounds with a six-membered A ring, 3 and 4, are mainly in the enamine form III.On protonation, 3 and 4 change into the E and Z isomeric mixture of the enol tautomer II.The seven-membered-ring compound 5 is a mixture of the imine I and the enamine III tautomers.