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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 22, Number 2
BKCSDE 22(2)
February 20, 2001 

Construction of Dihydro-1,4-dioxins: Synthesis of Dihydro-1,4-dioxin-3-carboxanilides
Hoh-Gyu Hahn, Kee Hyuk Chang, Kee Dal Nam
Agrochemical, Fungicide, Pesticide, Dihydro-1,4-dioxin, a, b-Unsaturated carboxanilide.
A new methodology for construction of dihydro-1,4-dioxin skeleton was described. Introduction of thio group at the α-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.
149 - 153
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