Title : ( Synthesis of 3,6-diaryl-1,4,5-thiadiazepines from substituted 2-thiocyano acetophenone and investigation of reaction mechanism )
Authors: Mohammad Rahimizadeh , Babak Feizyzadeh , Mehdi Bakavoli , Hossein Eshghi ,
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Abstract
In this work, we have studied the reaction of substituted 2-thiocyanoacetophenone and hydrazine hydrate as a novel and simple pathway for the preparation of the substituted 1,4,5-thiodiazepine ring system. The mechanism of this reaction revealed that in the initial step condensation of hydrazine with carbonyl groups of substituted 2-thiocyanoacetophenons 2a–2f gives the corresponding substituted aromatic dithiocyano azide intermediates which in turn undergo cyclization to1,4,5-thiadiazepines in the presence of hydrazine. This cyclization is a novel method for the preparation of sulfide bond from the reaction of hydrazine and a dithiocyano intermediate. An account of the reaction mechanism is given.
Keywords
, 2-thiocyanoacetophenons; hydrazine; thiocyanic esters; 1, 4, 5-thiadiazepine, 1, 3-oxathiole
@article{paperid:1034317,
author = {Rahimizadeh, Mohammad and Feizyzadeh, Babak and Bakavoli, Mehdi and Eshghi, Hossein},
title = {Synthesis of 3,6-diaryl-1,4,5-thiadiazepines from substituted 2-thiocyano acetophenone and investigation of reaction mechanism},
journal = {Journal of Sulfur Chemistry},
year = {2013},
volume = {34},
number = {3},
month = {June},
issn = {1741-5993},
pages = {276--283},
numpages = {7},
keywords = {2-thiocyanoacetophenons; hydrazine; thiocyanic esters; 1;4;5-thiadiazepine; 1;3-oxathiole},
}
%0 Journal Article
%T Synthesis of 3,6-diaryl-1,4,5-thiadiazepines from substituted 2-thiocyano acetophenone and investigation of reaction mechanism
%A Rahimizadeh, Mohammad
%A Feizyzadeh, Babak
%A Bakavoli, Mehdi
%A Eshghi, Hossein
%J Journal of Sulfur Chemistry
%@ 1741-5993
%D 2013
