The condensation of oxazoles with dienophiles is of the diene synthesis type, the final reaction products being substituted pyridine bases. The review deals with the literature data concerning the preparative applications of the condensation and the elucidation of the theoretical features of this process. In conclusion of the review, the application of heterodiene synthesis with participation of oxazoles in the preparation of vitamin B 6 and its analogues is discussed. The bibliography comprises 38 references.
CONTENTS
A convenient and general method is proposed for the synthesis of 5'-nucleotide phosphonate analogs starting from 5-deoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose which can easily be produced in preparative quantities from D-glucose. Phosphonate IIIe was synthesized by means of the Arbuzov reaction between 3-O-benzoyl-6-bromo-5,6-dideoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose and triethyl phosphite. The consecutive acetolysis, condensation with uracil and N6-benzoyladenine bis-trimethylsilyl derivatives and deblocking possessed phosphonate analogs of 5'-nucleotides in good yields. The intermediate 5-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose derivatives were used for the preparation of homonucleosides.
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