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A convenient synthesis of 5- and 8-nitroquinazoline-2,4-dione derivatives

✍ Scribed by D. Aziane; M. Soukri; A. El Hakmaoui; S. Lazar; M. Akssira; E. M. Essassi; G. Guillaumet

Publisher
Journal of Heterocyclic Chemistry
Year
2002
Tongue
English
Weight
62 KB
Volume
39
Category
Article
ISSN
0022-152X

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✦ Synopsis

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(1__H__)‐one(TIBO).

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