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A convenient synthesis of 5‐ and 8‐nitroquinazoline‐2,4‐dione derivatives
Author(s) -
Aziane D.,
Soukri M.,
El Hakmaoui A.,
Lazar S.,
Akssira M.,
Essassi E. M.,
Guillaumet G.
Publication year - 2002
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570390204
Subject(s) - chemistry , curtius rearrangement , carbon disulfide , tricyclic , pyridine , nitro , stereochemistry , smiles rearrangement , condensation , medicinal chemistry , organic chemistry , alkyl , physics , thermodynamics
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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