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Die photochemische Reduktion von 4,6‐Dimethyl‐2‐pyrimidinol
Author(s) -
Pfoertner KarlHeinz
Publication year - 1975
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19750580324
Subject(s) - chemistry , methanol , nitrous acid , medicinal chemistry , catalysis , stereochemistry , organic chemistry
π,π*‐Excitation of 4,6‐dimethyl‐2‐pyrimidinol in methanol leads to an addition product 5 whereas in 2‐propanol a dihydrodimer 3 is formed. By acid catalysis the dihydrodimer gives the 5, 9‐methano‐2 H ‐pyrimido[5,6‐ e ] [1,3]diazepine‐2,7(1 H )‐dione 7 which with stronger acids rearranges to the 2 H ‐cyclopentapyrimidin‐2‐one 8 . Nitrous acid reacts with the dihydrodimer yielding the dioxime of 2‐hydroxy‐4,6‐pyrimidinedicarbaldehyde.
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