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On triazoles XVI . The reaction of 5‐amino‐1,2,4‐triazoles with β‐ and γ‐oxo esters. A novel N ‐carbonylation reaction
Author(s) -
Reiter József,
Vágáa Pál,
EssesReiter Klóra,
Pongó László,
Molnár Hilda
Publication year - 1988
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570250628
Subject(s) - chemistry , alicyclic compound , carbonylation , yield (engineering) , ring (chemistry) , derivative (finance) , organic chemistry , reaction conditions , reaction mechanism , amino esters , condensation , medicinal chemistry , catalysis , carbon monoxide , materials science , physics , economics , financial economics , metallurgy , thermodynamics
5‐Amino‐1,2,4‐triazoles reacted with alifatic β‐oxo‐esters to yield besides the unexpected 1,2,4‐triazolo‐[1,5‐ a ]‐1,3,5‐benzotriazepin‐5‐one derivative 7 either the corresponding esters 5 and 6 or a 1:2 condensation product 8. To the contrary alicyclic and heterocyclic β‐oxo‐esters formed in the above reaction only derivatives 7. The proposed mechanism of the formation of 7 involving a novel N ‐carbonylation reaction was proved by the isolation of the by‐products and the intermediate of the reaction. Repeating the above reaction with a γ‐oxo‐ester, namely the ethyl levulinate, derivatives 17 and 18 , respectively, representing two new ring systems were obtained.