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A facile synthesis of unsymmetrical heterocyclic azines by cyclodesulfurization: Reaction of methyl arylalkylidenehydrazinecarbodithioates with diamines
Author(s) -
Lin Ai Jeng,
Klayman Daniel L.
Publication year - 1985
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.5570220101
Subject(s) - chemistry , ethylenediamine , azine , diamine , primary (astronomy) , hydrogen sulfide , medicinal chemistry , condensation , amine gas treating , organic chemistry , polymer chemistry , sulfur , physics , astronomy , thermodynamics
A new and facile synthesis of unsymmetrical heterocyclic azines is described. Methyl arylalkylidenehydraz‐inecarbodithioates, prepared by the condensation of ketones or aldehydes with methyl hydrazinecarbodithioate, were heated under reflux with various diamines in ethanol. Secondary diamines, such as N,N ′‐dimethyl‐ethylenediamine, N,N ′‐dimethyl‐1,3‐diaminopropane or N,N ′‐dimethyl‐ o ‐phenylenediamine, reacted smoothly with loss of hydrogen sulfide to give good yields of unsymmetrical azines. However, primary diamines, such as ethylenediamine or o ‐phenylenediamine, and primary/secondary diamines, such as N ‐methylethyl‐enediamine and N ‐methyl‐1,3‐diaminopropane gave, instead, only the corresponding uncyclized thiosemi‐carbazones. A cyclodesulfurization mechanism for azine formation is discussed.