L-(+)-Tryptophan methyl ester derived polymeric microbeads as an efficient heterogeneous catalyst for green synthesis of 2-amino-4-(nitromethyl)-4H-chromene-3- carbonitriles

Authors: AYŞE HALIÇ POSLU, BİLGEN OSMAN, YUNUS KAYA, ÖMER KOZ, GAMZE KOZ

Abstract: The cross-linked microbeads with average diameter of 106-300 μm, [poly(EGDMA-MATrp)], were obtained by copolymerization reaction of N-methacryloyl-L-(+)-tryptophan methyl ester (MATrp) with ethylene glycol dimethacrylate (EGDMA) and successfully applied as a heterogeneous catalyst in conjugate addition reaction of nitromethane to substituted 2-iminochromenes in aqueous media. A variety of 2-amino-4-(nitromethyl)-4H-chromene-3-carbonitriles has been synthesized in good yields. Polymeric microbeads were very durable and reused 5 times without a significant loss of activity. DFT calculations and experimental results revealed the significant role of π-π interactions as well as hydrogen bonding in the reaction mechanism.

Keywords: Polymeric microbeads, L-(+)-tryptophan methyl ester, nitromethane addition, π-π interaction, DFT calculation

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