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2H-Pyran-2-one-3-carbothioamide derivatives: Synthesis and reaction with hydrazine hydrate

✍ Scribed by Malika Makhloufi-Chebli; Maamar Hamdi; Artur M. S. Silva; Olivier Duval; Jean-Jacques Helesbeux


Publisher
Journal of Heterocyclic Chemistry
Year
2009
Tongue
English
Weight
103 KB
Volume
46
Category
Article
ISSN
0022-152X

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✦ Synopsis


Abstract

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N‐Aryl‐4‐hydroxy‐6‐methyl‐2__H__‐pyran‐2‐one‐3‐carbothiamides and N‐aryl‐4‐hydroxycoumarin‐3‐carbothiamides were synthesized by the reaction of arylisothiocyanates with 4‐hydroxy‐6‐methylpyran‐2‐one and 4‐hydroxycoumarin, respectively. Novel products 3‐[bis(arylamino)methylene]‐6‐methyl‐2__H__,4__H__‐pyran‐2,4‐diones and N,N′‐diaryl‐4‐hydroxycoumarin‐3‐carboximidamides have also been obtained in the same reactions. Novel 4‐acetoacetyl‐3‐phenylamino‐4,5‐dihydro‐5__H__‐pyrazol‐5‐ones were synthesized from the reaction of N‐aryl‐4‐hydroxy‐6‐methyl‐2__H__‐pyran‐2‐one‐3‐carbothiamides with an excess of hydrazine. The structure of all compounds was established by NMR and mass spectra. J. Heterocyclic Chem., (2009).


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2,4,5-Substituted furan-3(2H)-ones: Synt
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-ones (3) were obtained from some 2,3-dihydro-furan-2,3-diones with a few Wittig reagents ( 2). The compounds of 3 with glycin and hydrazines (4a,b) produced 2,3-dihydro- . All the reaction mechanisms were discussed by utilizing the similar reaction pathways. Structures of these compounds were deter