Premium
On triazoles. XXXIII . The reaction of potassium triazolyldithiocarbonates with dihaloalkanes
Author(s) -
Pongó LÁSzló,
Sohár PÁL,
Reiter JÓZsef,
Dvortsák Péter,
Bujtás György
Publication year - 1994
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.5570310450
Subject(s) - chemistry , potassium , yield (engineering) , ring (chemistry) , azine , medicinal chemistry , stereochemistry , organic chemistry , materials science , metallurgy
The reaction of potassium (5‐amino‐3‐Q‐1,2,4‐triazolyl)dithiocarbonates 2 with 1,ω‐dihaloalkanes 7‐10 to yield ω‐haloalkyldithiocarbonates 11‐12 , ω‐alkylene‐bis(dithiocarbonates) 13‐15 and different by‐products as the corresponding 7,8‐dihydro[1,2,4]triazolo[1,5‐ c ][1,3,5]thiadiazepine‐5(9 H )‐thione ( 16 ), 7,8,9,10‐tetrahy‐dro[1,2,4]triazolo[1,5‐ c ][1,3,5]thiadiazocine‐5‐thione ( 17 ) and 1,7‐dihydro‐5 H ‐1,2,4‐triazolo[1,5‐ c ][1,3,5]thiadi‐azine‐5‐thione ( 22 ) derivatives all three representing novel ring systems were obtained. Repeating the reactions with dipotassium salts 3 the corresponding iminodithietans 18 , imino‐1,3‐dithiolanes 19 and imino‐1,3‐dithianes 20 were obtained. Unexpectively, the imino‐1,3‐dithiolanes ( 19 ) rearranged to the corresponding thiazolidines 24‐27 under rather mild conditions. A possible mechanism is proposed for this rearrangement.