Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Construction of Dihydro-1,4-dioxins: Synthesis of Dihydro-1,4-dioxin-3-carboxanilides

  • Published : 20010200
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Abstract

A new methodology for construction of dihydro-1,4-dioxin skeleton was described. Introduction of thio group at the ${\alpha}-position$ of 8 followed by chlorination gave 11, which was to prevent an enolization as well as to promote the facile nucleophilic substitution reaction of ethylene glycol giving 16 in equilibrium with cyclic ether 19. Removal of thio group of 19 and dehydration in the presence of an acid catalyst gave dihydro-1,4-dioxin 21. In case of electron withdrawing trifluoromethyl group is subsituted in C-2, 18 was converted to the corresponding dihydro-1,4-dioxin 20 by the halogenation of hydroxy followed by treatment of triethylamine.

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References

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Cited by

  1. ChemInform Abstract: Construction of Dihydro-1,4-dioxins: Synthesis of Dihydro-1,4-dioxin-3-carboxanilides. vol.33, pp.14, 2002, https://doi.org/10.1002/chin.200214158
  2. [CpRu]‐Catalyzed Carbene Insertions into Epoxides: 1,4‐Dioxene Synthesis through SN1‐Like Chemistry with Retention of Configuration vol.126, pp.24, 2001, https://doi.org/10.1002/ange.201402994
  3. [CpRu]‐Catalyzed Carbene Insertions into Epoxides: 1,4‐Dioxene Synthesis through SN1‐Like Chemistry with Retention of Configuration vol.53, pp.24, 2001, https://doi.org/10.1002/anie.201402994