A facile synthesis of 3-amino-2,5-dihydropyridazines and 4-deazatoxoflavin analogues via [3+3] atom combination
Open Access
- 31 March 2016
- journal article
- Published by European Journal of Chemistry in European Journal of Chemistry
- Vol. 7 (1), 73-80
- https://doi.org/10.5155/eurjchem.7.1.73-80.1371
Abstract
Michael addition reactions of arylhydrazone derivatives with different functionalized α-cyanoacrylamides were conducted and yielded new pyridazine-4-carboxamide compounds. A further reaction with acetic anhydride was investigated resulting in the formation of a 4-deazatoxoflavin analogue. A one step synthesis of 4-deazatoxoflavin was also carried out by reacting azaenamine with N-carbamoyl-2-cyano-3-phenylacrylamide to give deazatoxoflavin. Unambiguous structural elucidation was done using 2D-HMBC spectroscopy.Keywords
This publication has 29 references indexed in Scilit:
- New pyridazine–fluorine derivatives: Synthesis, chemistry and biological activity. Part IIEuropean Journal of Medicinal Chemistry, 2013
- Diels–Alder Cycloaddition for Fluorophore Targeting to Specific Proteins inside Living CellsJournal of the American Chemical Society, 2011
- A novel synthesis of 3-(substituted)pyrimido[4,5-c]pyridazine-5,7(1H,6H)-dionesTetrahedron Letters, 2010
- Synthesis of Novel Spiro Cyclic 2-Oxindole Derivatives of 6-Amino-4H-Pyridazine via [3+3] Atom Combination Utilizing Chitosan as a CatalystSynlett, 2009
- Synthesis and properties of 3,4-disubstituted 1-methylpyrimido(4,5-c)pyridazine-5,7(1H,6H)-diones (3,4-disubstituted 4-deazatoxoflavins) and 3,4-disubstituted 4-deazatoxoflavin bound to polystyrene and their use in autorecycling oxidation of amines.CHEMICAL & PHARMACEUTICAL BULLETIN, 1984
- Syntheses and properties of 4-deazatoxoflavins and related compounds.CHEMICAL & PHARMACEUTICAL BULLETIN, 1982
- Syntheses of 1,6-dimethylpyrimido(4,5-c)pyridazine-5,7(1H, 6H)-diones (4-deazatoxoflavins) and their use in the autorecycling oxidation of alcohols and amines.CHEMICAL & PHARMACEUTICAL BULLETIN, 1981
- Untersuchungen an Diazoverbindungen und Aziden, XXI. Synthese und Isomerisierung von 2,3‐Diazabicyclo[3.1.0]hex‐2‐enen–eine neue Variante der Diazogruppen‐ÜbertragungEuropean Journal of Inorganic Chemistry, 1979
- Antibiotics. I. Synthesis of 1,6-Dimethyl-5,7-dioxo-1,5,6,7-tetrahydropyrimido [5,4-e] as-Triazine (Toxoflavin) and Related CompoundsJournal of the American Chemical Society, 1962
- On the origin of the toxicity of toxoflavinBiochimica et Biophysica Acta, 1961