Premium
On the formation and reactivity of N (2), N (2′)‐tetrasubstituted 2,4‐diamino‐5‐(2‐amino‐4‐thiazolyl)thiazoles
Author(s) -
Flaig Ronald,
Hartmann Horst
Publication year - 1997
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.5570340433
Subject(s) - chemistry , reagent , thiazole , electrophile , medicinal chemistry , pyridine , pyridazine , sodium nitrite , reactivity (psychology) , isothiocyanate , salt (chemistry) , phenyl isothiocyanate , sodium salt , organic chemistry , catalysis , medicine , alternative medicine , pathology , inorganic chemistry
By the reaction of weak bases with N (2)‐disubstituted 2‐amino‐4‐thiazoliniminium chlorides 3, easily available by the reaction of thioureas 1 with α‐chloroacetonitrile 2, N (2), N (2′)‐persubstituted 2,4‐diamino‐5‐(2‐amino‐4‐thiazolyl)thiazoles 8 are formed. These new bis‐thiazoles react, as exemplified with the dimorpholino derivative 8a, with different electrophilic reagent, such as phenyl isothiocyanate 9, 4‐nitro‐phenyldiazonium salt 11, or 4‐dialkylaminobenzaldehydes 13 at their 5 H ‐substituted thiazole moieties to give the corresponding thioanilides 10, azo compounds 12, and methine dyes 14, respectively. With sodium nitrite and the Vilsmeier reagent the thiazole 8a is transformed, via unstable intermediates, into the tricyclic 2,7‐dimorpholinothiazolo[4,5‐ c ]thiazolo[4,5‐ e ]pyridazine 16 and 2,7‐dimorpholinothiazolo[4,5‐ b ]thiazolo[4,5‐ d ]pyridine 19, respectively.