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

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Poslu A. H., OSMAN B., Kaya Y., Koz O., Koz G.

TURKISH JOURNAL OF CHEMISTRY, vol.46, no.5, pp.1642-1650, 2022 (SCI-Expanded) identifier identifier identifier identifier

  • Publication Type: Article / Article
  • Volume: 46 Issue: 5
  • Publication Date: 2022
  • Doi Number: 10.55730/1300-0527.3467
  • Journal Name: TURKISH JOURNAL OF CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Academic Search Premier, Chemical Abstracts Core, TR DİZİN (ULAKBİM)
  • Page Numbers: pp.1642-1650
  • Keywords: Polymeric microbeads, L-(+)-tryptophan methyl ester, nitromethane addition, Tr-Tr interaction, DFT calculation, MICHAEL ADDITION, CYCLIZATION, SQUARAMIDE, STACKING
  • Bursa Uludag University Affiliated: Yes

Abstract

The cross-linked microbeads with average diameter of 106-300 mu m, [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 Tr-Tr interactions as well as hydrogen bonding in the reaction mechanism.