Propargyloxy compounds

The allyloxy and propargyloxy compounds are easily prepared by the opening of mono-substituted epoxides with sodium aryl tellurolates, followed by allylation and propargyla-tion of the obtained -hydroxytellurides, submitted to irradiation with a sun lamp in the presence of hexabutylditin, and suffer group-transfer cyclization under 5-exo-mode to give the 2,4-disubstituted tetrahydrofuran derivatives. ... 

Furo[2,3-r/]pyrimidines can also be obtained from other 6-substituted-pyrimidines. For example, the 6-chloropyrimidine (219) is converted to the 6-propargyloxy compound (220) which cyclizes to the derivative (221) upon heating <84H(22)2217>. The formation of a 6-methyl isomer is accounted for by a Claisen rearrangement of the 6-allyloxy group (Scheme 16). 

A recent report of 6-substituted androst-4-ene-3,17-dione analogues synthesized by Shionogi has been released. Details are lacking but suggest that the 6-azido, -thiocyanato, and propargyloxy compound (no stereochemical details) are potent competitive inhibitors of AR and that unspecified examples were shown to significantly reduce ovarian oestrogen secretion in the rat [157]. 

A series of N-propargylaminophosphines (15)—(19) has been prepared in order to study their propensity to rearrange (15)—(17) were thermally stable, but (18) and (19) rearranged spontaneously to the A-methyl-3-phosphinopro-penal imines (20) and (21), respectively. This contrasts with the behaviour of the analogous propargyloxy compounds (22) which give allenic phosphine oxides. ... 

Decomposition of propargyloxy-l,2,3,4-thiatriazole (154) resulted in almost quantitative formation of the allenyl isocyanate (156). If the same reaction was carried out in the presence of hydrogen sulfide compound (157) was obtained, clearly demonstrating propargyl cyanate (155) as... 

Hydrogenation of the 1-propargyl and 1-allyl derivatives of 63 (R = H) over Pd/CaC03 or Pd/C gave the 1-propyl compound,103 273 whereas 2-propargyloxy-4-oxo-4A/-pyrido[l,2- ]pyrimidine yielded the 2-propyloxy compound.273 Catalytic hydrogenation of the 2-alkoxy- and 2-aralkoxy-4-oxo-4A/-pyrido[l,2- ]pyrimidines was accompanied by the hydrogenolysis of the substituents in position 2.112,114... 

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