Synthesis of 4-(2-hydroxyaryl)-3-nitro-4H-chromenes |
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Authors: | H Surya Prakash Rao K GeethaM Kamalraj |
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Institution: | Department of Chemistry, School of Physical, Chemical and Applied Sciences, Pondicherry University, Pondicherry 605 014, India |
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Abstract: | A combinatorial library of 4-(2-hydroxyaryl)-3-nitro-4H-chromenes was synthesized in high yield by C4-SMe substitution in N-alkyl/phenyl 4-(methylthio)-3-nitro-4H-chromen-2-amines with a variety of phenols. The reaction always provided C2 substitution in the phenol ring, dictated by hydrogen bond interactions between the phenolic hydroxyl group and the nitro group in 3-nitro-4H-chromenes. Reduction of the nitro group with concomitant hydrolysis of the enamine in 4-(2-hydroxyaryl)-3-nitro-4H-chromenes with Zn, Ac2O in AcOH furnished hybrid amino-acid lactone incorporating ortho-tyrosine and phenyl alanine moieties. |
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Keywords: | Nitroketene Electrophlic substitution 4-Aryl-4H-chromenes Hybrid amino acid |
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