Construction of dihydro-1,4-dioxins: Synthesis of dihydro-1,4-dioxin-3-carboxanilides

Authors
Hahn, HGChang, KHNam, KD
Issue Date
2001-02-20
Publisher
KOREAN CHEMICAL SOC
Citation
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, v.22, no.2, pp.149 - 153
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.
Keywords
agrochemical; fungicide; pesticide; dihydro-1,4-dioxin; alpha,beta-unsaturated carboxanilide
ISSN
0253-2964
URI
https://pubs.kist.re.kr/handle/201004/140704
Appears in Collections:
KIST Article > 2001
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