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2‐Chloro‐4,5‐dihydroimidazole, III. Synthesis, Reactions, and Crystal Structure of 2‐(Alkylthio)‐7,8‐dihydroimidazo[1,2‐ a ]‐1,3,5‐triazine‐4(6 H )‐thiones
Author(s) -
Sączewski Franciszek,
Gdaniec Maria
Publication year - 1987
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.198719870816
Subject(s) - chemistry , triazine , ammonium thiocyanate , medicinal chemistry , alkylation , thiocyanate , derivative (finance) , crystal structure , stereochemistry , polymer chemistry , organic chemistry , catalysis , financial economics , economics
Treatment of 2‐chloro‐4,5‐dihydroimidazolium hydrogen sulfate ( 1 ) with ammonium thiocyanate results in the formation of 7,8‐dihydroimidazo[1,2‐ a ]‐1,3,5‐triazine‐2,4(3 H ,6 H )‐dithione ( 3 ), which undergoes selective alkylation under alkaline conditions to give 2‐(alkylthio)‐7,8‐dihydroimidazo[1,2‐ a ]‐1,3,5‐triazine‐4(6H)‐thiones 4a–f . 2‐Methylthio derivative 4a serves as a substrate for the synthesis of 2,3‐dihydroimidazo[1,2‐ a ]‐[1,2,4]triazolo[4,3‐ c ][1,3,5]triazine‐5(6 H )‐thione ( 7 ). The structure of 4c is proved by X‐ray analysis.
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