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Ring closure reactions of cyclic 2‐arylaminomethylene‐1,3‐diones
Author(s) -
Van Tinh Dang,
Fischer Michaela,
Stadlbauer Wolfgang
Publication year - 1996
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.5570330358
Subject(s) - chemistry , acridine , quinoline , ring (chemistry) , closure (psychology) , thermal decomposition , medicinal chemistry , bicyclic molecule , stereochemistry , organic chemistry , economics , market economy
5‐Arylaminomethylene compounds such as 5‐arylaminomethylenepyrimidine‐2,4,6‐triones 2 or 2‐phenylaminomethylenephenalene‐1,3‐dione 13 cyclize by thermolysis via migration of the arylamino group to pyrimido[4,5‐ b ]quinoline‐2,4‐diones 6 or 7‐oxo‐7 H ‐naphtho[1,8‐ bc ]acridine 15 , respectively. 2‐Phenylaminomethylenecyclohexane‐1,3‐dione 8 cyclizes to 9,9‐dimethyl‐9,10‐dihydrophenanthridin‐7(8 H )‐one 11 without rearrangement.