Three‐Component Synthesis of 7‐Hydroxy‐7‐polyfluoroalkylhexahydroimidazo[1,2‐<i>a</i>]­pyridin‐5(1<i>H</i>)‐ones

Goryaeva, M. V.; Burgart, Yanina V.; Kudyakova, Yulia S.; Ежикова, М. А.; Кодесс, М. И.; Слепухин, П. А.; Салоутин, В. И.

doi:10.1002/ejoc.201500822

Cited by 19 publications

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“…We recently developed a straightforward approach to 7‐hydroxy‐7‐polyfluoroalkylhexahydroimidazo[1,2‐ a ]pyridin‐5‐ones 1 based on a three‐component cyclization of readily available fluorinated 3‐oxo esters, aldehydes, and 1,2‐diamines (Scheme ). We found that when heterocycles 1a – 1i are heated under acidic conditions, they undergo both a dehydration at the C‐6–C‐7 bond and a ring‐opening of imidazolidine moiety at the C‐8a–N‐1 bond to form 1‐(2‐aminoethyl)pyridones 2 – 4 (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

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Synthesis of Pyridone Derivatives from 7‐Hydroxy‐7‐polyfluoroalkylhexahydroimidazo[1,2‐a]pyridin‐5‐ones

et al. 2017

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The synthesis of 1‐(2‐aminoethyl)‐6‐alkyl‐4‐polyfluoroalkylpyridin‐2‐ones based on the acidic cleavage of 7‐hydroxy‐7‐polyfluoroalkylhexahydroimidazo[1,2‐a]pyridin‐5‐ones is reported. Depending on the reaction conditions, the pyridones can be obtained as bases, salts, acetamides, or the products of intramolecular cyclization, dihydroimidazopyridines. High tuberculostatic activity was observed for some of the synthesized compounds.

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Section: Resultsmentioning

confidence: 99%

“…Column chromatography was carried out on Merck silica gel 60 (0.063–0.200 mm). Hexahydroimidazo[1,2‐ a ]pyridines 1a – 1i were obtained according to literature procedures . Glacial acetic acid and p ‐toluenesulfonic acid monohydrate were commercially sourced (purchased from Alfa Aesar).…”

Section: Methodsmentioning

confidence: 99%

Synthesis of Pyridone Derivatives from 7‐Hydroxy‐7‐polyfluoroalkylhexahydroimidazo[1,2‐a]pyridin‐5‐ones

et al. 2017

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“…Multicomponent synthesis is the most modern, simple and low-cost way to create new molecules from available starting reagents. Over the past 7 years, our group has been developing a new multicomponent approach that makes it possible to obtain various fluorine-containing heterocyclic compounds from commercially available polyfluoroalkyl-3-oxo esters, methyl ketones, and nucleophiles [ 31 , 32 , 33 , 34 ].…”

Section: Introductionmentioning

confidence: 99%

Multicomponent Domino Cyclization of Ethyl Trifluoropyruvate with Methyl Ketones and Amino Alcohols as A New Way to γ-Lactam Annulated Oxazacycles

et al. 2023

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A new route to bicyclic γ-lactams was found, which was proposed as a three-component cyclization of ethyl trifluoropyruvate with methyl ketones and 1,2-, 1,3-amino alcohols. As a result, a series of trifluoromethyl-substituted tetrahydropyrrolo [2,1-b]oxazol-5-ones and tetrahydropyrrolo[2,1-b][1,3]oxazine-6-ones was synthesized, in which the substituent at the nodal carbon atom was varied. The introduction of a twofold excess of ethyl trifluoropyruvate in reactions with amino alcohols and acetone made it possible to obtain the same bicycles, but functionalized with a hydroxyester fragment, which are formed due to four-component interactions of the reagents. Transformations with 2-butanone and aminoethanol lead predominantly to similar bicycles, while an analogous reaction with aminopropanol gives N-hydroxypropyl-2,3-dihydropyrrol-5-one. Almost all bicycles are formed as two diastereomers, the structure of which was determined using 1H, 19F, 13C NMR spectroscopy, including two-dimensional experiments and XRD analysis. A domino mechanism for the formation of tetrahydropyrrolo[2,1-b]oxazacycles was proposed, which was confirmed by their stepwise synthesis through the preliminary preparation of the aldol and bis-aldol from ethyl trifluoropyruvate and methyl ketones.

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Multicomponent Domino Reactions for the Synthesis of Variable Hydrogenated Imidazo[1,2‐a]pyridines

et al. 2021

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An effective synthetic approach was proposed to partially and fully hydrogenated imidazo[1,2-a]pyridines based on cyclizations of polyfluoroalkyl-3-oxo esters and ethylenediamine with aldehydes. It was found that acetic and propionic aldehydes react similar to the α,β-unsaturated crotonic and cinnamic aldehydes. The cyclizations of trifluoroacetoacetic ester with ethylenediamine and aldehydes led to the formation of ethyl 5-hydroxy-5-trifluoromethyloctahydroimidazo[1,2-a]pyridin-6-carboxylates, except for the reaction with acetaldehyde, where the main product was 7-hydroxy-7-trifluoromethylhexahydroimidazo[1,2-a]pyridin-5(1H)-one. The cyclizations of polyfluoroalkyl-3-oxo esters resulted in 6-(polyfluoroalkyl-1-hydroxyalkyl)tetrahydroimidazo[1,2-a]pyridin-5(3H)-ones, except for transformations with cinnamaldehyde, from which ethyl 5hydroxy-7-phenyl-5-polyfluoroalkyloctahydroimidazo-[1,2a]pyridin-6-carboxylates were isolated as by-products. These bicycles containing long polyfluoroalkyl substituents (R F > C 2 F 5 ) underwent haloform cleavage to form ethyl 7-phenyl-5oxooctahydroimidazo[1,2-a]pyridin-6-carboxylate. The regioand stereoisomeric structure of the synthesized bicycles was determined using 1 H, 19 F, 13 C NMR spectroscopy and X-ray. The domino mechanism was proposed for the formation of new tetra-, hexa-and octahydroimidazo[1,2-a]pyridines.

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Three‐Component Synthesis of 7‐Hydroxy‐7‐polyfluoroalkylhexahydroimidazo[1,2‐a]pyridin‐5(1H)‐ones

Cited by 19 publications

References 74 publications

Synthesis of Pyridone Derivatives from 7‐Hydroxy‐7‐polyfluoroalkylhexahydroimidazo[1,2‐a]pyridin‐5‐ones

Synthesis of Pyridone Derivatives from 7‐Hydroxy‐7‐polyfluoroalkylhexahydroimidazo[1,2‐a]pyridin‐5‐ones

Multicomponent Domino Cyclization of Ethyl Trifluoropyruvate with Methyl Ketones and Amino Alcohols as A New Way to γ-Lactam Annulated Oxazacycles

Multicomponent Domino Reactions for the Synthesis of Variable Hydrogenated Imidazo[1,2‐a]pyridines

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Three‐Component Synthesis of 7‐Hydroxy‐7‐polyfluoroalkylhexahydroimidazo[1,2‐a]­pyridin‐5(1H)‐ones

Cited by 19 publications

References 74 publications

Synthesis of Pyridone Derivatives from 7‐Hydroxy‐7‐polyfluoroalkylhexahydroimidazo[1,2‐a]pyridin‐5‐ones

Synthesis of Pyridone Derivatives from 7‐Hydroxy‐7‐polyfluoroalkylhexahydroimidazo[1,2‐a]pyridin‐5‐ones

Multicomponent Domino Cyclization of Ethyl Trifluoropyruvate with Methyl Ketones and Amino Alcohols as A New Way to γ-Lactam Annulated Oxazacycles

Multicomponent Domino Reactions for the Synthesis of Variable Hydrogenated Imidazo[1,2‐a]pyridines

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Three‐Component Synthesis of 7‐Hydroxy‐7‐polyfluoroalkylhexahydroimidazo[1,2‐a]pyridin‐5(1H)‐ones