Convenient Synthesis of 2,3-Dihydro-1,2,4-thiadiazoles, 4,5-Dihydro-1,3-thiazoles, and 1,3-Thiazoles through a [4+1]-Type Oxidative Ring Closure of 1,3-Thiaza-1,3-butadienes

Heterocycles ◽  
2020 ◽  
Vol 100 (6) ◽  
pp. 881
Author(s):  
Kazuaki Shimada ◽  
Megumi Isogami ◽  
Kitami Maeda ◽  
Rei Nishinomiya ◽  
Toshinobu Korenaga
Keyword(s):  
Ring Closure ◽  
Convenient Synthesis

Formation and Reactions of (1-Chloroalkyl)carbamoyl Chlorides. Synthesis of 1,2,4-Triazolidine-5-ones

1973 ◽  
Vol 51 (3) ◽  
pp. 333-337 ◽  
Author(s):  
Kinko Koyano ◽  
Colin R. McArthur
Keyword(s):  
Ring Closure ◽  
Convenient Synthesis ◽  
Effect Ring ◽  
Substituted Hydrazines ◽  
Nitrogen Bond

N-(α-Chlorobenzyl)carbaniloyl chloride and (α-chlorobenzyl)methylcarbamoyl chloride are formed by reaction of phosgene with N-benzylideneaniline and N-benzylidenemethylamine, respectively. Reaction of these carbamoyl chlorides with a number of nucleophiles is described, some of which cause cleavage of the benzyl to nitrogen bond while others give rise to substitution products without such cleavage. Of the latter type, substituted hydrazines react to effect ring closure to1,2,4-triazolidine-5-ones. The method serves as a convenient synthesis of these new heterocyclic systems.

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