D. Aziane, M. Soukri, A. E. Hakmaoui
Mar 1, 2002
Citations
0
Influential Citations
3
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
3-Nitrophthalic acid 1 was converted selectively to the two regioisomeric monoesters 2 and 3, which were subsequently transformed via Curtius rearrangement to the corresponding 5- and 8-nitroquinazoline-2,4-diones 4 and 5, respectively. The reduction of the nitro group produced 5- and 8-aminoquinazoline-2,4-diones 6 and 7, respectively, in good yields. The condensation of compounds 7b and 7c with carbon disulfide in pyridine afforded tricyclic derivatives 9, which are analogues of the HIV-1 reverse transcriptase inhibitor 4,5,6,7-tetrahydro-5-methylimidazo[4,5,1-jk][1,4]benzodiazepin-2(1H)-one(TIBO).