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Title: Synthesis of 12,13-dihydro-5-oxoquinolino[2,3-<i style="">a</i>]carbazoles, 3,11-dihydro-2,4-dioxopyrano[2,3-<i style="">a</i>]carbazoles and quinolino[2,3-<i style="">b</i>]carbazolo[6,5-<i style="">a</i>]pyran-7,8-diones
Authors: Sangeetha, V
Prasad, K J Rajendra
Keywords: 1-Hydroxycarbazoles
12,13-dihydro-5-oxoquinolino[2,3-<i style="">a</i>]carbazoles
3,11-dihydro-2,4-dioxopyrano[2,3-<i style="">a</i>]carbazoles
quinolino[2,3-<i style="">b</i>]carbazolo[6,5-<i style="">a</i>]pyran-7,8-diones
Issue Date: Jun-2006
Publisher: CSIR
Series/Report no.: <b>Int.Cl.<sup>8 </sup>C07D</b>
Abstract: The reaction of 1-hydroxycarbazoles <b style="">1a-d</b> with anthranilic acid in the presence of fused zinc chloride and phosphorus oxychloride at room temperature affords 1,7-dibenzoazocin-6,12-dione <b style="">2</b> in all the cases and the expected 12,13 dihydro-5-oxoquinolino[2,3-<i style="">a</i>]carbazoles <b style="">3a-d</b>. In another reaction, 1-hydroxycarbazoles <b style="">1a-d </b>with malonic acid in the presence of fused zinc chloride and phosphorus oxychloride at room temperature yields 3,11-dihydro-2,4-dioxopyrano[2,3-<i style="">a</i>]carbazoles <b style="">4a-d</b>. Further, the attempted synthesis of c/b fused quinolinodipyrano annelated carbazoles<b style=""> 7a-d</b> or <b style="">8a-d </b>or both from the reaction of 3,11-dihydro-2,4-dioxopyrano[2,3-<i style="">a</i>]carbazoles <b style="">4a-d</b> with vinyl acetate and 2,4-dihydroxyquinoline <b style="">6</b> results in the formation of new dimerised product, quinolino[2,3-<i style="">b</i>]carbazolo[6,5-<i style="">a</i>]pyran-7,8-diones <b style="">9a-d</b>. A plausible mechanism has been suggested to explain this reaction.
Description: 1487-1491
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.45B(06) [June 2006]

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