Journal of Organic Chemistry p. 5589 - 5594 (1990)
Update date:2022-08-04
Topics:
Datta, Apurba
Ila, Hiriyakkanavar
Junjappa, Hiriyakkanavar
A novel cycloaromatization reaction leading to substituted and annelated ethyl 2-hydroxy-6-(methylthio)benzoates 4 by condensation of α-oxo-ketene dithioacetals with an excess of Reformatsky reagent from ethyl bromoacetates through intermediate dienes 3 has been described.The reaction has also been extended for the synthesis of substituted ethyl 3-hydroxy-5-(methylthio)stilbenecarboxylates 9 by using cinnamoyl ketene dithioacetals 8.A few of the benzoates 4 were desulfurized to the corresponding salicylate derivatives 5.Reaction of acyclic oxo ketene dithioacetals with ethyl(bromozincio)acetate in the presence of cuprous iodide afforded 4- (or 4,5-)substituted 6-(methylthio)pyran-2-ones 15 in moderate to good yields.A probable mechanism for the formation of 15 is suggested.Cyclization of the acyclic dienes 3 or the carbinols 10 with ammonium acetate in refluxing acetic acid afforded the corresponding 4- (or 4,5-)substituted 6-(methylthio)-2(1H)-pyridones 22.
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Doi:10.1055/s-0035-1561313
(2016)Doi:10.1248/cpb.38.936
(1990)Doi:10.1039/jr9630005706
(1963)Doi:10.1021/jm00129a002
(1989)Doi:10.1007/BF00808927
(1990)Doi:10.1016/S0040-4039(00)94563-5
(1990)