A Regioselective One-Pot, Three Component Synthesis of 6-Aryl-4-cyano-3(2H)-pyridazinones in Water

Abstract

A series of 4-cyano-3(2H)-pyridazinones bearing different aryl substituents in the 6-position of the pyridazinone ring was synthesized regioselectively using a novel efficient one-pot three component reaction of alkyl 2-cyanoacetates with arylglyoxals in the presence of hydrazine hydrate at room temperature in water.

Crystal structure of 3-(4-hydroxy-3-methoxyphenyl)-7,7-dimethyl-7,8-dihydrocinnolin-5(6H)-one

“…In continuation of our recent reports on synthesis of pyridazine derivatives, [11][12][13][14][15][16][17][18] here we report the X-ray crystal structure of 3-(4-hydroxy-3-methoxyphenyl)-7,7-dimethyl-7,8-dihydrocinnolin-5(6H)one prepared by reaction of 2-(4-hydroxy-3-methoxyphenyl)-2-oxoacetaldehyde with dimedone in the presence of hydrazine hydrate. 11…”

Regioselective one-pot, three component synthesis of ethyl 6-aryl-3-propylpyridazine-4-carboxylates in water

“…21 These pharmacological and technological properties of pyridazines encourage the development of methods for their synthesis and functionalization. In continuation of our interest in the synthesis of various pyridazine derivatives, [22][23][24][25][26] we decided to investigate the three-component reaction of arylglyoxals, ethyl butyrylacetate and hydrazine hydrate which is extended to the regioselective synthesis of ethyl 6-aryl-3-propylpyridazine-4-carboxylates as a new series of three substituted pyridazines.…”

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.…”