A Regiospecific One-Pot, Three Component Synthesis of 4-Aryl-6,8-dimethylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-diones as New Potential Monoamine Oxidase Inhibitors

Abstract

A series of new 4-aryl-6,8-dimethylpyrimido[4,5-c]pyridazine-5,7(6H,8H)-diones have been synthesized via three component reaction of 1,3-dimethylbarbituric acid with arylglyoxals in the presence of hydrazinium dihydrochloride in ethanol. All of these derivatives may act as potential monoamine oxidase inhibitors.

An Efficient One-pot Two-component Protocol for Regio- and Chemoselective Synthesis of 5-Aryloyl-1,3,7,9-tetraalkyl-2,8-dithioxo-2,3,8,9-tetrahydro-1H-pyrano[2,3-d:6,5-d′]dipyrimidine-4,6(5H,7H)-diones

“…Consequently, MCRs have emerged as a powerful tool for delivering molecular libraries needed in combinatorial approaches for the assembly and lead identification of bioactive compounds. [21] Based on the above considerations and in continuance of our previous research into the arylglyoxal-mediated synthesis of various heterocycles, [22][23][24][25][26][27][28][29][30][31][32] we have found that 1,3-dialkyl thiobarbituric acids undergo a tandem Knoevenagel-Michael condensation with arylglyoxals leading to the formation of a substituted pyranopyrimidine skeleton. Herein, we report an efficient two-component strategy for synthesis of symmetrically substituted 5-aryloyl-1H-pyrano[2,3-d]pyrimidine 1.…”

Synthesis, Characterization, and Docking Evaluations of New Derivatives of Pyrimido[4,5‐c]pyridazine as Potential Human AKT1 Inhibitors

“…Morrison and co‐workers were described the cyclizations of glyoxals with 6‐hydrazinoisocytosines while the synthesis of 3‐(substituted)pyrimido[4,5‐ c ]pyridazine‐5,7(1 H ,6 H )‐diones were performed by Turbiak through the condensation of 3‐methyl‐6‐(1‐methylhydrazinyl)uracil with phenyl and alkyl glyoxal monohydrates . A series of new 4‐aryl‐6,8‐dimethylpyrimido[4,5‐ c ]pyridazine‐5,7(6 H ,8 H )‐dione derivatives were synthesized via three component reactions of 1,3‐dimethylbarbituric acid with arylglyoxals in the presence of hydrazinium dihydrochloride .…”

Single crystal X-ray structure of 3-amino-5-(4-chlorophenyl)pyridazine-4-carbonitrile

“…7 Hence, the synthesis of pyridazine derivatives has been studied for many years. [8][9][10][11][12][13][14] In continuation of recent reports on synthesis of pyridazine derivatives, [15][16][17][18][19][20][21][22][23] we would like to report the single crystal X-ray structure of 3-amino-5-(4-chlorophenyl)pyridazine-4-carbonitrile prepared by a one-pot three-component reaction of malononitrile with corresponding arylglyoxal in the presence of hydrazine hydrate at room temperature. 23 …”