Convenient Approaches towards the Synthesis of Novel Pyrano[2,3‐a]carbazoles |
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| Authors: | Kumaresan Prabakaran Matthias Zeller Paul S Szalay Karam J Rajendra Prasad |
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| Institution: | 1. Department of Chemistry, Bharathiar University, , Coimbatore, 641 046 India;2. Department of Chemistry, Youngstown State University, , Ohio, 44555;3. Department of Chemistry, Muskingum University, , New Concord, Ohio, 43762 |
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| Abstract: | Previously not easily accessible pyrano2,3‐a]carbazoles were synthesized in highly convergent syntheses avoiding multistep procedures from readily available 1‐hydroxycarbazoles. Substituted pyrano2,3‐a]carbazoles were produced by three different methods by treatment of the 1‐hydroxycarbazoles with dimethyl acetylene dicarboxylate (DMAD) and triphenylphoshine, by reaction with ethyl 2‐methylacetoacetate in the presence of ZnCl2/POCl3, and by reaction with trifluoroacetic acid followed by Wittig reaction with (carbethoxymethylene) triphenylphosphorane. The article also highlights the optimization of reaction conditions and strategies to avoid formation of byproducts for all three types of reactions. |
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