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Studies on the synthesis of heterocyclic compounds. Part IX. Action of N,N ‐dimethylformamide dimethylacetal on some oximino‐β‐dicarbonyl compounds
Author(s) -
Plescia Salvatore,
Daidone Giuseppe,
Sprio Vincenzo
Publication year - 1982
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.5570190626
Subject(s) - chemistry , hydrazine (antidepressant) , dimethylformamide , hydrazide , hydrate , medicinal chemistry , ethanol , organic chemistry , solvent , chromatography
3‐Oximino‐2,4‐pentanedione ( 1 ) and ethyl 2‐oximino‐3‐oxobutanoate ( 6 ) reacted with N,N ‐dimethylformamide dimethylacetal (DFDA) to give 1,7‐bisdimethylamino‐3,5‐dioxo‐4‐methoximinohepta‐1,6‐diene ( 4 ) and ethyl 5‐dimethylamino‐2‐methoximino‐3‐oxo‐4‐pentenoate ( 8 ), respectively. When compounds 4 and 8 were treated with hydrazine hydrate, they gave O ‐methyldipyrazol‐3(5)‐ylketoxime ( 5 ) and ethyl 2‐methoximino‐3(5)‐pyrazolylethanoate ( 9 ) together with its corresponding hydrazide 10 , respectively. Upon action of DFDA on 3‐oximino‐2,4‐pentanedione ( 1 ) at ‐20° an explosive crystalline product was obtained. On the other hand, the reaction of 3‐acetoximino‐2,4‐pentanedione ( 11 ) with DFDA at ‐20° afforded a product which in ethanol solution, spontaneously deacetylated to give 1‐dimethylamino‐3,5‐dioxo‐4‐oximinohexa‐1‐ene ( 13 ). The structures of all the new compounds were assigned on the basis of satisfactory analytical and spectroscopic data.