On triazoles. XXXIII. The reaction of potassium triazolyldithiocarbonates with dihaloalkanes

LÁSzló Pongó, P. Sohár, JÓZsef Reiter, Péter Dvortsák, György Bujtás

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Abstract

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(9H)‐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‐5H‐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.

Original languageEnglish
Pages (from-to)997-1004
Number of pages8
JournalJournal of Heterocyclic Chemistry
Volume31
Issue number4
DOIs
Publication statusPublished - 1994

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ASJC Scopus subject areas

  • Organic Chemistry

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