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Reactions of uracils, 7. Synthesis and novel consecutive thermal [1,5]‐sigmatropic rearrangements of 6‐(alkylamino)‐5‐ethenyluracils
Author(s) -
Mátyus Péter,
Zólyomi Gábor,
Eckhardt Gert,
Wamhoff Heinrich
Publication year - 1986
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19861190317
Subject(s) - chemistry , sigmatropic reaction , saponification , substituent , medicinal chemistry , thermal , organic chemistry , physics , meteorology
Additional 6‐(alkylamino)‐5‐ethenyluracils ( 2d, 7 ) have been prepared for investigating substituent effects in thermal reactions. Like 2a , upon heating in Dowtherm® A 2d and 7 afford after saponification 6‐amino‐5‐(ethoxycarbonyl[phenyl]ethyl)uracils 4 and 8 , respectively. After refluxing in xylene the intermediary imines 11 and 12 can be isolated. Deuteration experiments reveal consecutive thermal [1,5]H‐migrations ( 2a – D 1 → 4 ‐D 1 , and 4 ‐D 2 ; 2a ′‐D 2 → 4 ′‐D 1 ). The mechanism is discussed.