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Azido/tetrazole equilibrium in the thiazoloacridinone series
Author(s) -
Hanoun JeanPierre,
Faure Robert,
Galy JeanPierre,
Elguero José
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.5570330337
Subject(s) - chemistry , tetrazole , tautomer , derivative (finance) , sodium hydride , medicinal chemistry , equilibrium constant , ion , inorganic chemistry , organic chemistry , financial economics , economics
Compounds 2‐azido‐6 H ‐thiazolo[5,4‐ a ]acridin‐11‐one 3 and 2‐azido‐6‐butylthiazolo[5,4‐ a ]acridin‐11‐one 4 have been prepared for the first time. The azido/tetrazole equilibria of the most soluble compound 4 has been studied in six solvents. The resulting tautomeric equilibrium constants have been compared with those of 2‐azido‐4,5‐dimethylthiazole 1 and 2‐azidobenzothiazole 2 . The rather insoluble NH derivative 3 when dissolved in DMSO contains 66% of tetrazole 3b while the corresponding anion (obtained by adding sodium hydride) is all in the tetrazole 13b form.