New π-Conjugated Ferrocenyl-Substituted Heterocyclic Systems Containing Electron-Deficient Aromatic Nitrogen Heterocycles

Antuf’eva, A. D.; Дмитриев, М. В.; Майорова, О. А.; Мокрушин, И. Г.; Galeev, A. R.; Shklyaeva, E. V.; Абашев, Г. Г.

doi:10.1134/s1070428018090142

Cited by 2 publications

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“…Substituted β‐chloropropenal, bearing easily eliminated nucleophilic group in the position 3, has been employed as a scaffold for the construction of heterocyclic ring . The reaction of 3‐ferrocenyl‐3‐chloroprop‐2‐enal 36 and acetylacetone 37 with ammonia acetate under reflux in glacial acetic acid for 1 h readily furnishes the corresponding 1‐(2‐meth‐yl‐6‐ferrocenylpyridin‐3‐yl)ethenone 38 (Scheme ) . In this work, pyridine 38 was characterized by X‐ray structural analysis and used in the synthesis of pyrimidin‐2‐amines.…”

Section: Synthesis Of Pyridinesmentioning

confidence: 99%

α,β‐Unsaturated Aldehydes as C‐Building Blocks in the Synthesis of Pyridines, 1,4‐Dihydropyridines and 1,2‐Dihydropyridines

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2019

Asian J Org Chem

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N-heterocycles are ubiquitous structural units in a variety of biologically active compounds, pharmaceutical preparations, and natural complex molecules. Thousands of original scientific papers are published annually on various aspects of the formation of nitrogenous heterocycles and the study of their chemical and biological properties. Among them, the synthesis of pyridines and their dihydrogenated derivatives attracts the attention of chemists, which develop synthetic techniques, including those ones based on α,βunsaturated aldehydes. The minireview summarizes and highlights the recent advancements in the construction of pyridines, 1,2-dihydropyridines, and 1,4-dihydropyridines from transformations of 2-alkenals, covering the publications of the last five years. formation of the arylidene moiety A. Then, the Michael addition of dinitrile 51 at the C=C bond of the molecule A lead to the intermediate B which attaches the proton to give intermediate C. The intramolecular nucleophilic attack of NH 2 -group on cyanocarbon of molecule C followed by aromatization into Scheme 10. Ammonia-based synthesis of 1-(2-meth-yl-6-ferrocenylpyridin-3-yl)ethenone 38. Scheme 11. Synthesis of pyridines 41 using enaminones 39. Scheme 12. Use of enals 43 in FeCl 3 -catalyzed reaction with β-enamino esters 42.these compounds for medicine. In the review, it is shown that the use of α,β-unsaturated aldehydes in the synthesis of 1,2dihydropyridines remains rather limited.The material presented in the review demonstrates the wide possibilities of using α,β-unsaturated aldehydes for the synthesis of six-membered azaheterocycles -pyridines, 1,2-and 1,4-dihydropyridines. The advantages of the discussed methods are available starting materials, simple operational procedures, use of environmentally friendly catalysts. This allows chemist to get structurally diverse products with high yields, to reduce time and energy, to avoid isolation of intermediate compounds and thus increase powerful productivity of reaction. Conflict of InterestThe authors declare no conflict of interest.

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Section: Synthesis Of Pyridinesmentioning

confidence: 99%