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An Efficient Synthesis of Pyrrolo[1,2‐a] or Pyrido[1,2‐a]benzo[4,5]imidazo[1,2‐c]quinazoline Derivatives in Ionic Liquids Catalyzed by Iodine

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2-(1H-benzo[d]imidazol-2-yl)anilines reacted with haloketones including 5-chloropentan-2-one and 6-chlorohexan-2-one catalyzed by iodine, giving benzo[4,5]imidazo[1,2-c]pyrrolo[1,2-a]quinazoline and 6H-benzo[4,5]imidazo[1,2-c]pyrido[1,2-a]quinazoline derivatives, respectively. This domino-type reaction formed two new heterocycles and three new covalent bonds in… Click to show full abstract

2-(1H-benzo[d]imidazol-2-yl)anilines reacted with haloketones including 5-chloropentan-2-one and 6-chlorohexan-2-one catalyzed by iodine, giving benzo[4,5]imidazo[1,2-c]pyrrolo[1,2-a]quinazoline and 6H-benzo[4,5]imidazo[1,2-c]pyrido[1,2-a]quinazoline derivatives, respectively. This domino-type reaction formed two new heterocycles and three new covalent bonds in one-pot procedure and provided a green method for the synthesis of fused pentacyclic heterocycles bearing both quinazoline and benzimidazole moieties in ionic liquids.

Keywords: benzo; benzo imidazo; quinazoline derivatives; catalyzed iodine; ionic liquids

Journal Title: Journal of Heterocyclic Chemistry
Year Published: 2017

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