One pot synthesis of fused [1,2-a]pyrrole from 1,6-dioxo-2,4-diene and haloalkyl primary amine |
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Authors: | Shyh-Shiann Juang Long Fu Wang Chi Wi Ong |
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Institution: | a Chia Nan University of Pharmacy and Science, Tainan, Taiwan b Department of Chemistry, National Sun Yat Sen University, Kaoshiung, 804, Taiwan |
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Abstract: | The one pot synthesis of fused 2,3-dihydropyrrolizine 4a and 6,7-dihydro-5H-indolizine 4b involving the intermolecular dehydrative condensation of 1-phenyl-1,6-dioxo-hepta-2,4-diene 1 with 2-chloroethylamine and 3-chloropropylamine followed by the intramolecular cyclization of the intermediary products 2-(1-chloroalkyl-5-methylpyrrol-2-yl)-1-phenylethanones 3a,b in the presence of a base such as Na2CO3 and NaHCO3 is described. These also led to the concurrent formation of the oxidatively dimerized product 2,3-bis-1,5-(2-chloroalkyl)-1-H-pyrrol-2-yl]-1,4-diphenylbutane-1,4-dione 5a,b whereby the structure was further confirmed by X-ray analysis. |
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Keywords: | One-pot synthesis Intramolecular alkylation N-fused pyrrolo ring |
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