Abstract:The Heck reaction is one of the most studied coupling reactions and is recognized with the Nobel Prize in Chemistry. Thousands of articles, hundreds of reviews and a number of books have been published on this topic. All reviews are written exhaustively describing the various aspects of Heck reaction and refer to the work done hitherto. Looking at the quantum of the monographs published, and the reviews based on them, we found a necessity to summarize all reviews on Heck reaction about catalysts, ligands, suggested mechanisms, conditions, methodologies and the compounds formed via Heck reaction in one review and generate a resource of information. One can find almost all the catalysts used so far for Heck reaction in this review.
A highly efficient protocol of Ni(II) metal complex, [Ni(quin)], catalyzing N-formylation and N-acylation of amines with moderate to excellent yields, using N,N-dimethylformamide and N,N-dimethylacetamide in the presence of imidazole, is described here. The protocol shows broad substrate scope for aliphatic, aromatic, and heterocyclic amines.
A Cu‐(II) catalyzed N‐formylation and N‐acylation of amines with moderate to excellent yields, using N, N‐dimethyl formamide (DMF) and N, N‐dimethyl acetamide (DMA) as a formyl and acylating sources in the presence of 1,2,4‐triazole is reported. This novel, highly efficient and simple protocol shows broad substrate scope for aliphatic, aromatic, and heterocyclic amines. In addition, the conditions to prevent N‐formylation and N‐acylation impurities in the C−N cross coupling of amines and aryl halides are described typically when DMF and DMA are used as solvents, with various catalysts, ligands, and bases.
The efficiently designed and synthesized novel 2,4‐dimethyl‐5‐((E)‐3‐phenyl‐3‐oxoprop‐1‐enyl)‐1H‐pyrrole‐3‐carboxylic acid derivatives has been described here which is encouraged by the anticancer activities associated with sunitinib and semaxanib. Synthesized compounds were characterized by 1H NMR, 13C NMR and high‐resolution mass spectrometry (HRMS). They are evaluated for in vitro antiproliferative properties on cancer cell lines as well as antibacterial activity against gram‐positive and gram‐negative species. The bioassay results revealed that several compounds exhibit potential antiproliferation activity. Among them, the lead compound 2,2,2‐trifluoroethyl 5‐((E)‐3‐(3‐fluoro‐4‐(trifluoromethyl)phenyl)‐3‐oxoprop‐1‐enyl)‐2,4‐dimethyl‐1H‐pyrrole‐3‐carboxylate (9 g) showed the most potent anticancer activity against MDA‐MB‐231 and PC‐3 cancer cell line with GI50 values of 5.51 and 5.15 μg/mL and subsequently more active than sunitinib (GI50: 6.50 μg/mL) against PC‐3. Same compound 9 g also exhibits the most potent antibacterial activity against gram‐positive bacteria Bacillus subtilis and Staphylococcus aureus with IC50 of 1.44 and 1.54 μg/mL. In silico prediction, shows that all seven potent compounds obeyed Lipinski rule for druglikeness. Structure‐activity relationship (SAR) study reflect the activity enhance with electron withdrawing group on aryl ring and replacement of acid by its bioisosteres i. e. amide and ester group. These studies have successfully identified many newly synthesized compounds as potential anticancer as well as antibacterial agent for further development.
A crucial chemoselective O-formyl and O-acyl protection of alkanolamines, phenoxyethanols, and alcohols in the presence of amines catalyzed by Ni(ii) and Cu(ii) complexes with 8-hydroxyquinoline in a homogeneous medium is achieved.
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