PYRIDAZINE DERIVATIVES. XXIV.[1] EFFICIENTN-METHYLATION OF DIVERSELY SUBSTITUTED 3(2H)-PYRIDAZINONES USINGN,N-DIMETHYLFORMAMIDE DIMETHYLACETAL

2002 ◽  
Vol 32 (11) ◽  
pp. 1675-1680 ◽  
Author(s):  
Eddy Sotelo ◽  
Enrique Raviña
Keyword(s):  
Dimethylformamide Dimethylacetal ◽  
Pyridazine Derivatives

Synthesis of Dimethyl 1-(Hetero)aryl-4-oxo-1,4-dihydropyridazine- 3,5-dicarboxylates from Dimethyl 3-Oxopentane-1,5-dioates

2008 ◽  
Vol 63 (4) ◽  
pp. 407-414 ◽  
Author(s):  
David Pahovnik ◽  
Uroš Uršič ◽  
Uroš Grošelj ◽  
Anton Meden ◽  
Jurij Svete ◽  
...  
Keyword(s):  
Dimethylformamide Dimethylacetal ◽  
Alternative Method ◽  
Arenediazonium Salts ◽  
Pyridazine Derivatives

AbstractDimethyl 3-oxopentane-1,5-dioate (dimethyl acetone-1,3-dicarboxylate) (1) was transformed first with (hetero)arenediazonium salts 3a - j into dimethyl 2-[(hetero)arylhydrazono]pentane-1,5-dioates 4a - j followed by reaction with N,N-dimethylformamide dimethylacetal (DMFDMA) to afford, without isolation of intermediates 5a - j, dimethyl 1-(hetero)aryl-4-oxo-1,4-dihydropyridazine-3,5- dicarboxylates 6a - j. An alternative method represents transformation of 1 with DMFDMA into dimethyl 2-[(dimethylamino)methylidene]-3-oxopentane-1,5-dioate (7) followed by treatment with (hetero)arenediazonium salts 3a - c, j to give pyridazine derivatives 6a - c,j.

New Pyrrolo[1,2-b]pyridazine Derivatives by 1,3-Dipolar Cycloaddition of Mesoionic Oxazolopyridazinone

2008 ◽  
Vol 59 (11) ◽  
Author(s):  
Miron Teodor Caproiu ◽  
Florea Dumitrascu ◽  
Mino R. Caira
Keyword(s):  
Nmr Spectroscopy ◽  
Elemental Analysis ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Pyridazine Derivatives ◽  
New Compounds

New pyrrolo[1,2-b]pyridazine derivatives 8a-f were synthesized by 1,3-dipolar cycloaddition reaction between mesoionic 1,3-oxazolo[3,2-b]pyridazinium-2-oxides and diethyl or diisopropyl acetylenedicarboxylate as alkyne dipolarophiles. The structures of the new compounds were assigned by elemental analysis and NMR spectroscopy.

Synthesis and Herbicidal Activities of Novel 3-N-Substituted Amino-6-methyl-4-(3-trifluoromethylphenyl)pyridazine Derivatives

2008 ◽  
Vol 56 (15) ◽  
pp. 6567-6572 ◽  
Author(s):  
Han Xu ◽  
Xu-Hong Hu ◽  
Xiao-Mao Zou ◽  
Bin Liu ◽  
You-Quan Zhu ◽  
...  
Keyword(s):  
Pyridazine Derivatives

Synthesen mit Nitrilen, LVII [1]. Zur Reaktivität von Aminomethylen-malonsäuredinitrilen gegenüber Aldehyden und Orthoestern / Syntheses with Nitriles, LVII [1]. The Reactivity of Aminomethylene-malononitriles with Aldehydes and Orthoesters

1979 ◽  
Vol 34 (11) ◽  
pp. 1580-1586 ◽  
Author(s):  
Martin Mittelbach ◽  
Hans Junek
Keyword(s):  
Double Bond ◽  
Aromatic Aldehydes ◽  
Dimethylformamide Dimethylacetal

Abstract Condensation of aminomethy lene-malononitrile (1a) with aromatic aldehydes and dimethylformamide-dimethylacetal, resp., leads to benzylidene-malononitriles (2a, b) and to dimethylaminomethylene-malononitrile (2e), resp. A mechanism of this cleavage of a C=C double bond is discussed. Several substituted enaminonitriles (1e-i) are prepared and the reactivity against aldehydes is studied. Thus, condensation of 3-Amino-2-cyano-crotononitrile (1e) with aldehydes leads to 2-amino-4-phenyl-1,3-butadiene-1,1-dicarbo-nitriles (3). 4-Oxo-2-phenyl-1,2,3,4-tetrahydro-5-pyrimidine-carbonitriles (4) are yielded by the reaction of 3-amino-2-cyano-crotonic-carboxamide (1h) and 3-amino-2-cyano-cinnamamide (1i), resp., with aldehydes. Condensation of 1h and 1i with ethyl ortho-formate leads to 3,4-dihydro-4-oxo-pyrimidine-carbonitriles (6).

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