Amination of chloro-substituted heteroarenes with adamantane-containing amines

Abel, Anton S.; Grigorova, O. K.; Averin, Alexei D.; Maloshitskaya, O. A.; Бутов, Г. М.; Savelyev, E. N.; Orlinson, B. S.; Новаков, И. А.; Beletskaya, I. P.

doi:10.1007/s11172-016-1516-7

Cited by 4 publications

(4 citation statements)

References 21 publications

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“…Catalyst-free monoamination of 2,6-dichloropyrazine 2 and 1,3-dichloroisoquinoline 3 with a wide scope of adamantane-containing amines was studied earlier [31]. The known protocol [31] was employed for the synthesis of N-(2-(1-adamantyloxy)ethyl)-6chloropyrazin-2-amine 6 and N-[2-(1-adamantyloxy)ethyl]-3-chloroisoquinolin-1-amine 7 in 82 and 89% yields (Scheme 3) for further studies of the substitution of the chlorine in these compounds. The synthesis of adamantane-containing 4,6-diaminopyrimidines was studied using a model compound 5a with Pd(dba) 2 as a precatalyst (Scheme 4, Table 1).…”

Section: Resultsmentioning

confidence: 99%

“…For the aforementioned reasons, the aim of this work is the elaboration of the approach to adamantane-containing 4,6-diaminopyrimidines, 2,6-diaminopyrazines, and 1,3-diaminoisoquinolines. Selective monoamination of the corresponding dichloroheteroarenes can be accomplished in high yields under catalyst-free conditions [31]. Non-catalytic introduction of the second amino group is seriously hindered by the electron donor effect of the first amino group.…”

Section: Introductionmentioning

confidence: 99%

“…HRMS (MALDI-TOF): m/z [M + H] + calcd for C 16 H 23 ClN 3 : 292.1575; observed: 292.1540. Syntheses of N-(2-(1-Adamantyloxy)ethyl)-6-chloropyrazin-2-amine (6) and N-[2-(1-Adamantyloxy)ethyl]-3-chloroisoquinolin-1-amine (7) were previously reported in ref [31]…”

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confidence: 99%

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Mono- and Diamination of 4,6-Dichloropyrimidine, 2,6-Dichloropyrazine and 1,3-Dichloroisoquinoline with Adamantane-Containing Amines

et al. 2021

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N-heteroaryl substituted adamantane-containing amines are of substantial interest for their perspective antiviral and psychotherapeutic activities. Chlorine atom at alpha-position of N-heterocycles has been substituted by the amino group using convenient nucleophilic substitution reactions with a series of adamantylalkylamines. The prototropic equilibrium in these compounds was studied using NMR spectroscopy. The introduction of the second amino substituent in 4-amino-6-chloropyrimidine, 2-amino-chloropyrazine, and 1-amino-3-chloroisoquinoline was achieved using Pd(0) catalysis.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Mono- and Diamination of 4,6-Dichloropyrimidine, 2,6-Dichloropyrazine and 1,3-Dichloroisoquinoline with Adamantane-Containing Amines

et al. 2021

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“…99.9%) owing to its high acid density and highly exposed sulfamic acid sites. Notably, the ketal yield and acid density gradually decreases from 99.9% to 89.5% and 2.12 to 1.93 mmolg -1 with PVC-DTA-SO3H to PVC-PHA-SO3H, respectively, which should be due to a fact that the increase of the steric hindrance of the amination reagent reduced the nucleophilic substitution reaction activity of the amino group with PVC [54][55][56][57] and the growth of the amino-linked carbon chain reduces its nucleophilic ability [58,59], resulting in a decrease in the number of amino groups grafted on the PVC carbon chain, which eventually led to a decrease in the number of sulfonic acid groups connected by the chlorosulfonation reaction.…”

Section: The Ketalization Reaction Under Different Conditionsmentioning

confidence: 97%

Sulfamic acid functionalized PVC: a remarkably efficient heterogeneous reusable catalyst for the acid-catalyzed reactions

Wang,

Zhang,

Liu

et al. 2023

Res Chem Intermed

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Sulfamic acid functionalized polyvinyl chloride catalysts (PVC-N-SO3H, N=EDA, DTA, TTA, TPA, PHA) were prepared as efficient heterogeneous solid acid catalysts via two-steps treatment processes. The prepared catalysts were characterized by X-ray diffraction analysis (XRD), TG thermograms/derivative thermogravimetric (TG/DTG), transmission electron microscope (TEM), elemental mappings and energy-dispersive spectroscopy analyses (STEM-EDS), and FT-IR measurements (FT-IR) as well as acid-base back-titration. The acetalization of aldehydes (ketones) and alcohols to acetal (ketal) was selected to evaluate the acid catalytic performance of PVC-N-SO3H. The results showed that PVC-EDA-SO3H exhibit excellent activity and reusability due to its highly exposed sulfonic acid sites, high surface acid density (2.28 mmol g -1 ) for the conversion of aldehydes (ketones) to acetal (ketal). This new solid acid has obvious advantages in reusability and catalytic activity over traditional homogeneous concentrated sulfuric acid and heterogeneous sulfonated resin catalysts. Furthermore, PVC-EDA-SO3H exhibited an excellent catalytic performance in the synthesis of 12 acetals (ketals) as well as a good compatibility in the hydroxyalkylation of phenol with formaldehyde to bisphenol F (BPF) and the esterification reaction of oleic acid and methanol to biodiesel. More importantly, it could also be recovered easily and used repeatedly at least nine times without an obvious decrease in the activity.

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1,3-Dehydroadamantane and Its Derivatives: A Versatile Synthetic Platform for the Preparation of Functional Compounds with a Cage Structure. A Review

Mokhov,

Butov,

Novakov

2023

Dokl Chem

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Amination of chloro-substituted heteroarenes with adamantane-containing amines

Cited by 4 publications

References 21 publications

Mono- and Diamination of 4,6-Dichloropyrimidine, 2,6-Dichloropyrazine and 1,3-Dichloroisoquinoline with Adamantane-Containing Amines

Mono- and Diamination of 4,6-Dichloropyrimidine, 2,6-Dichloropyrazine and 1,3-Dichloroisoquinoline with Adamantane-Containing Amines

Sulfamic acid functionalized PVC: a remarkably efficient heterogeneous reusable catalyst for the acid-catalyzed reactions

1,3-Dehydroadamantane and Its Derivatives: A Versatile Synthetic Platform for the Preparation of Functional Compounds with a Cage Structure. A Review

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