Applicability of the previously described rearrangement of 2-oxo-2-phenylethyl 2-amino-benzoate leading to 2-phenyl-2-hydroxymethyl-2,3-dihydroquinazolin-4(1H)-one has been studied. To test the limits of the reaction, various starting compounds such as 2-oxopropyl 2-aminobenzoate, 2-oxo-2-phenylethyl 2-aminobenzoate and 3,3-dimethyl-2-oxobutyl 2- aminobenzoate as well as some of their corresponding N-methyl and N-phenyl analogues were used. The structure-reactivity dependence was observed giving the expected products only in specific cases and in limited yields. Structure of the dihydroquinazolin-4(1H)-one skeleton was unambiguously confirmed with use of X-ray analysis of two selected compounds. Finally, an alternative way for the preparation of the desired derivatives was developed.
Study of anthranilate cyclisation to 2-hydroxymethyl-2,3- dihydroquinazolin-4(1H)-ones and an alternative synthetic route
BERTOLASI, Valerio
2010
Abstract
Applicability of the previously described rearrangement of 2-oxo-2-phenylethyl 2-amino-benzoate leading to 2-phenyl-2-hydroxymethyl-2,3-dihydroquinazolin-4(1H)-one has been studied. To test the limits of the reaction, various starting compounds such as 2-oxopropyl 2-aminobenzoate, 2-oxo-2-phenylethyl 2-aminobenzoate and 3,3-dimethyl-2-oxobutyl 2- aminobenzoate as well as some of their corresponding N-methyl and N-phenyl analogues were used. The structure-reactivity dependence was observed giving the expected products only in specific cases and in limited yields. Structure of the dihydroquinazolin-4(1H)-one skeleton was unambiguously confirmed with use of X-ray analysis of two selected compounds. Finally, an alternative way for the preparation of the desired derivatives was developed.I documenti in SFERA sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
