✍ Scribed by Jagdish M. Patel; Shubhangi S. Soman
No coin nor oath required. For personal study only.
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Several new furoflavanones (3a‐3I) have been synthesized from the in‐situ generated chalcones by the reaction of ortho‐hydroxy acetyl benzofuran and aryl aldehyde in presence of piperidine. Ethanolic sodium hydroxide (1%) gave chalcones (2a‐2I) as the exclusive product. Flavindogenides (3‐arylidene flavanones) (5a‐5d) have been isolated as the co‐product along with chalcones and flavanones in cases where excess of aryl aldehyde was used. The stereochemistry of 3‐arylidene flavanones has been established by the preparation of both Z (6) and E (5a‐5d) diastereomers. Single crystal X‐ray diffraction data shows the flavanone ring to exist in quasi chair conformation with phenyl ring equatorial. Furoflavanones were finally dehydrogenated to furoflavones (4a‐4I) using DDQ (2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone). The compounds have been screened for in‐vitro cytotoxicity against human cancer cell lines.
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