14135-64-9Relevant academic research and scientific papers
A new mild synthetic route to N-arylated pyridazinones from aryldiazonium salts
El Bakouri, Ouissam,Cassú, Daniel,Solà, Miquel,Parella, Teodor,Pla-Quintana, Anna,Roglans, Anna
supporting information, p. 8073 - 8076 (2014/07/08)
An efficient method for the synthesis of N-arylated pyridazinones from potassium 2-furantrifluoroborate and aryldiazonium salts is described. The reaction was run in water at 0-5 °C in short reaction times and without any catalyst or additive. A mechanistic proposal is made based on the experimental data and DFT calculations. the Partner Organisations 2014.
The Reaction of Meldrum's Acid with α-Dicarbonyl Monohydrazones: A New Synthesis of Pyridazin-3-ones
McNab, Hamish,Stobie, Ian
, p. 1845 - 1854 (2007/10/02)
Treatment of the monohydrazones of α-dicarbonyl compounds with Meldrum's acid gives the condensation products (13)-(19) under standard conditions.Reaction of pyruvaldehyde 2-phenylhydrazone or 2-t-butylhydrazone with Meldrum's acid at 80 deg C gives the corresponding 2-substituted-2,3-dihydro-6-methyl-3-oxo-pyridazine-4-carboxylic acids (29) and (30).Cyclisation of the other N-monosubstituted condensation products (13), (14), (16), (18), and (19) to 3-oxopyridazine-4-carboxylic acids (31)-(35) can be effected under basic conditions.Gas-phase pyrolysis of the N-aryl derivatives (13)-(16) at 550 deg C and 10E-2 Torr gives N-arylpyridazin-3-ones (38)-(41) while the N-t-butyl derivatives (18) and (19) at 750 deg C and 10E-2 Torr give N-unsubstituted pyridazin-3-ones (44) and (45) by additional loss of 2-methylpropene. 2-t-Butylpyridazin-3-ones (42) and (43) can be isolated from the same precursors under milder conditions (500 deg C and 10E-2 Torr).Pyrolysis of the N,N-dimethyl derivative (17) gave only polymeric material.
