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Synthesis 2025; 57(10): 1755-1761
DOI: 10.1055/a-2538-6958
DOI: 10.1055/a-2538-6958
paper
An Unexpected Synthesis of 2,3-Bis(methylthio)-1,4-di(het)arylbut-2-ene-1,4-diones and Their Cyclocondensation with Hydrazine for the Synthesis of 4,5-Bis(methylthio)-3,6-di(het)arylpyridazines
K.M. thanks DBT Glue (Grant No. BT/PR23078/MED/29/1253/2017 dated 22-03-2018) and VGST Project (Grant No. Ksteps/VGST/GRD-681/KFIST(L1)/2018 dated 27-08-2018) for financial support.
Dedicated to Prof. K. S. Rangappa on the occasion of his 70th birthday.
Abstract
An unexpected formation of novel 2,3-bis(methylthio)-1,4-di(het)arylbut-2-ene-1,4-diones is reported, when methyl ketones are reacted with α-oxodithioesters in the presence of sodium hydride in DMF followed by treatment with methyl iodide. A potential application of these key intermediates for the synthesis of unreported 4,5-bis(methylthio)-3,6-di(het)arylpyridazines is explored by reacting them with hydrazine in the presence of potassium hydroxide in isopropyl alcohol. Possible mechanisms for the formation of 2,3-bis(methylthio)-1,4-di(het)arylbut-2-ene-1,4-diones and 4,5-bis(methylthio)-3,6-di(het)arylpyridazines are proposed.
Key words
hydrazine - pyridazine - 2,3-bis(methylthio)-1,4-di(het)arylbut-2-ene-1,4-diones - cyclocondensation - unexpectedSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2538-6958.
- Supporting Information
Publication History
Received: 31 December 2024
Accepted after revision: 13 February 2025
Accepted Manuscript online:
13 February 2025
Article published online:
19 March 2025
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