Abstract
Abstract The Hoesch reaction of 6-hydroxy-2,3-dihydrobenzo[b]furan with 2,3,4-trimethoxyphenylacetonitrile yielded 6-hydroxy-5-(2,3,4-trimethoxyphenylacetyl)-2,3-dihydrobenzo[b]furan. The cyclization of the dihydrobenzofuran with ethyl orthoformate-pyridine-piperidine gave dihydrodehydronepseudin, an isoflavone. The dehydrogenation of the above isoflavone with N.B.S. or Pd-G yielded dehydronepseudin. Nepseudin was derived by the reduction of dehydronepseudin with sodium borohydride and by subsequent oxidation with the chromium trioxidepyridine complex.
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