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The synthesis of 5-hydroxy chromenes

1985; NRC Research Press; Volume: 63; Issue: 10 Linguagem: Inglês

10.1139/v85-430

1480-3291

John W. ApSimon, L. W. Herman, C. P. Huber,

Multicomponent Synthesis of Heterocycles

The synthesis of 2,2-dimethyl-5-hydroxychromene (1d) is described. The synthesis of the analogous 5,7-dihydroxy derivatives, using similar conditions, yields the adduct 9 derived via a Bucherer type reaction. X-ray analysis of 9 demonstrated that a pyrrolidine group was in the 7-position, and that the 5-hydroxyl group was involved in a strong intramolecular hydrogen bond to the 4-keto oxygen atom.