Synthesis of Substituted Benzoxazepinones as Potential Anti-retroviral Drug Analogues
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Date
2001
Authors
Izunobi, J.U.
Familoni, O.B.
Alo, B.I.
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Abstract
The syntheses of 8-nitro-1,2,3,3a-tetrahydropyrrolo(1,2-a)[4,1]benzoxazepin-6-one 10 and 2-hydroxy-8-
nitro-1,2,3,3a-tetrahydropyrrolo(1,2-a)[4,1]benzoxazepine-4,6-dione 11 were achieved via a two-step
reaction pathway; condensation followed by dehydration. 2-Chloro -5-nitrobenzoic acid 5 was separately
condensed with L-pyrrolidine-2-methanol (L-prolinol) 6 and 4-hydroxy-L-pyrrolidine-2-carboxylic acid (4-
hydroxyl-L-proline) 7 to give the condensation products; N-(2’-carboxy-4’-nitrophenyl)-L-prolinol 8 and N-
(2’-carboxy-4’-nitrophenyl)-4-hydroxy-L-proline 9, respectively – precursors to the target molecules 10
and 11. N-(2’-carboxy-4’-nitrophenyl)-L-pyrrolidine-2-methanol 8 afforded 8-nitro-1,2,3,3a-tetrahydro
pyrrolo(1,2-a)[4,1]benzoxazepin-6-one 10 on dehydration with trifluoroacetic acid while N-(2’-carboxy-4’-
nitrophenyl)-4-hydroxy-L-pyrrolidine-2-carboxylic acid 9 in refluxing acetic anhydride gave 2-hydroxy-8-
nitro-1,2,3,3a-tetrahydropyrrolo(1,2-a)[4,1] benzoxazepine-4,6-dione 11, both in good yields.
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Research Subject Categories::NATURAL SCIENCES