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Title: Synthesis of 12,13-dihydro-5-oxoquinolino[2,3-a]carbazoles, 3,11-dihydro-2,4-dioxopyrano[2,3-a]carbazoles and quinolino[2,3-b]carbazolo[6,5-a]pyran-7,8-diones
Authors: Sangeetha, V
Prasad, K J Rajendra
Keywords: 1-Hydroxycarbazoles
Issue Date: Jun-2006
Publisher: CSIR
Series/Report no.: Int.Cl.8 C07D
Abstract: The reaction of 1-hydroxycarbazoles 1a-d with anthranilic acid in the presence of fused zinc chloride and phosphorus oxychloride at room temperature affords 1,7-dibenzoazocin-6,12-dione 2 in all the cases and the expected 12,13 dihydro-5-oxoquinolino[2,3-a]carbazoles 3a-d. In another reaction, 1-hydroxycarbazoles 1a-d 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-a]carbazoles 4a-d. Further, the attempted synthesis of c/b fused quinolinodipyrano annelated carbazoles 7a-d or 8a-d or both from the reaction of 3,11-dihydro-2,4-dioxopyrano[2,3-a]carbazoles 4a-d with vinyl acetate and 2,4-dihydroxyquinoline 6 results in the formation of new dimerised product, quinolino[2,3-b]carbazolo[6,5-a]pyran-7,8-diones 9a-d. 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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