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Thermolyzed products of naphth[1,2‐ d ]imidazo[2,1‐ b ]‐thiazole‐2,3‐dione
Author(s) -
Liu KangChien,
Shih BiJane
Publication year - 1986
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.5570230459
Subject(s) - chemistry , thiazole , yield (engineering) , medicinal chemistry , dimer , dimethylformamide , triazine , stereochemistry , organic chemistry , materials science , solvent , metallurgy
Themolysis of naphth[1,2‐ d ]imidazo[2,1‐ b ]thiazole‐2,3‐dione ( 1 ) in dimethylformamide gave an intermediate 2‐isocyanatonaphtho[1,2‐ d ]thiazole ( 2 ), which underwent [4 + 4] cyclodimerization to yield dinaphtho‐[1″,2″:4,5;1′″,2′″:4′,5′]dithiazolo[3,2‐ a :3′,2′‐ e ]‐1,3,5,7‐tetrazocine‐9,19‐dione ( 3 ). The possible [4 + 2] cycloadduct, 3‐(2‐naphtho‐[1,2‐ d ]‐thiazolyl)naphtho[1′,2′:4,5]thiazolo[3,2‐ a ]‐1,3,5‐triazine‐2,4‐dione ( 4 ), an usual dimer type of heterocyclic isocyanates was not produced. Discrimination between the two isomers was established on the basis of spectral analyses.