A green and practical one‐pot two‐step strategy for the synthesis of symmetric 3,6‐diarylpyridazines

Abstract

A simple, mild, and efficient synthesis of symmetric 3,6-diarylpyridazine derivatives using a green catalytic one-pot two-step reaction of aryl methyl ketones, arylglyoxal monohydrates, and hydrazine hydrate was developed. Environmentally benign nature, high atom-economy, no harmful byproduct, easy workup procedure, no column chromatography steps, and moderate to excellent yields of the products are the salient features of this new multicomponent-based methodology. K E Y W O R D S 3,6-Diarylpyridazine, aryl methyl ketone, arylglyoxal monohydrate, DABCO, one-pot, ZrOCl 2 Á 8H 2 O

A Simple and Efficient Regioselective and Chemoselective Synthesis of New Substituted 3‐Methyl‐6‐arylpyridazine‐4‐carboxamides and 5‐Oxo‐3‐aryl‐5,6‐dihydropyrido[4,3‐c]pyridazine‐8‐carbaldehydes

“…As in recent reports [8f, 8g, 9], the key evidence for the formation of the 6‐aryl regioisomer is the absence of shielded pyridazine C 6 ‐H singlet and the appearance of deshielded pyridazine C 5 ‐H proton singlet at δ = 8.12 ppm [8i, 9]. The 1 H‐NMR spectra of all the pyridazine products ( 5a–j ) showed two distinct broad singlets for each hydrogen of the amide NH 2 group at approximately δ = 7.92 and 8.25 ppm.…”

“…We have recently reported simple, efficient, and economic methods for the synthesis of a number of heterocyclic scaffolds . Because of the high solubility of arylglyoxal monohydrates in water and because this solvent allows for an environmentally friendly process, water was used as the preferred solvent for the optimization experiments and in the final preparative protocol.…”

Two different facile and efficient approaches for the synthesis of various N-arylacetamides via N-acetylation of arylamines and straightforward one-pot reductive acetylation of nitroarenes promoted by recyclable CuFe2O4 nanoparticles in water

“…So, designing new protocols for the synthesis of amides via straightforward one-pot reductive acetylation of aromatic nitro compounds without isolation of the arylamine intermediates is very interesting. In this regard, it should be noted that one-pot multicomponent reactions (MCRs) are remarkable instruments for versatile preparation of a wide diversity of organic compounds especially biologic active molecules which have advantages such as high atom economy, escape of time-consuming protection-deprotection steps, and environmentally friendliness, making them absolutely better than classical multistep synthetic pathways [27][28][29][30][31][32][33][34][35][36][37].…”

Novel edaravone-based azo dyes: efficient synthesis, characterization, antibacterial activity, DFT calculations and comprehensive investigation of the solvent effect on the absorption spectra

“…24 Dyes based on 5-pyrazolone, are especially extensively used in color photographic materials. [25][26][27] In the context of our general interest in the synthesis of heterocyclic compounds, [28][29][30][31][32][33][34][35][36][37][38][39][40][41] herein, we propose a facile synthesis of the new dyes based on edaravone due to the unique properties of this compound. The synthesis of the desired compounds is possible through the coupling reaction of azo compounds with edaravone (D1-D10).…”