Chemical Structure from Scientific Research

Skeletal editing of pyridine cores in drugs and drug derivatives. Compounds 42, 46, 48, 51, 52, 54 are obtained under condition A, whereas others are synthesized under condition B. All yields are isolated yields based on pyridine in a one-pot process unless stated otherwise. a The gram-scale yield (in parenthesis) by using condition A. b The gram-scale yield (in parenthesis) by using condition B under air. c Applying condition B with probenecid-derived alkyne (1.2 equiv.); the yield is based on the pyridine. d With condition A using (+)-delta-tocopherol derived aryne precursor (1 equiv.), 4-phenylpyridine (1.5 equiv.), DMAD (1.5 equiv.), MP (1.5 equiv.) and caesium fluoride (1.5 equiv.); the yield is based on the aryne precursor. e Combined yield of the two constitutional isomers.

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