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2005
Metathesis reactions
O 0286
Spiro-annulation of Barbituric Acid Derivatives and Its Analogues by Ring-ClosMetathesis Reaction. — Barbituric acid derivatives (I) and (V) as well as other
25- 052 ing
biologically important molecules such as tetronic acid (VIII), thiotetronic acid (XII),
and pyrazolone derivatives are diallylated under phase-transfer catalytic conditions.
The ring-closing metathesis reaction of the allylated products is performed in the presence of Grubbs' 1st generation catalyst yielding the corresponding spiro-annulated
compounds. In the case of tetronic acid (VIII), the unwanted O-allylated derivative (X)
can be converted into the desired isomer (IX) by Claisen rearrangement. For diallylation of thiotetronic acid (XII), a similar protocol is adopted and (XIII) is found to be
the major product. — (KOTHA*, S.; DEB, A. C.; KUMAR, R. V.; Bioorg. Med.
Chem. Lett. 15 (2005) 4, 1039-1043; Dep. Chem., Indian Inst. Technol., Bombay
400 076, India; Eng.) — H. Hoennerscheid
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