Brønsted acid catalyzed Prins-Ritter reaction for selective synthesis of terpenoid-derived 4-amidotetrahydropyran compounds

Sidorenko, A.Yu.; Kurban, Yu.M.; Peixoto, Andreia F.; Li-Zhulanov, Nikolai S.; Sánchez-Velandia, J.E.; Aho, Atte; Wärnå, Warna J.; Gu, Yanlong; Волчо, К. П.; Салахутдинов, Н. Ф.; Murzin, Dmitry Yu.; Агабеков, В. Е.

doi:10.1016/j.apcata.2022.118967

Cited by 11 publications

(4 citation statements)

References 51 publications

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“…From the results it is possible to notice that carbon based catalysts are the most efficient, rendering yields higher than 50 %, independently of the functionalization, which is in accordance with the recently published results on the Prins‐Ritter reaction of (−)‐isopulegol with benzaldehyde and acetonitrile [25] . A curious fact transversal to all experiments, was the dimerization of 1 a , to bis(1‐phenylethyl)ether 4 .…”

Section: Resultssupporting

confidence: 88%

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Sulfonic Acid‐Functionalized (Bio)Materials as Catalysts for Efficient Amide Bond Synthesis

et al. 2023

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Sulfonic acid carbon-(bio)based and natural clays-based catalysts were prepared and investigated for the first time as heterogeneous catalysts for amide bond synthesis by a Ritter reaction. The different SO 3 H-catalysts were screened using benzyl alcohol and acetonitrile as model substrates, and MWCNT-CSP revealed to be an efficient catalyst, affording the amide in 75 % yield. The practical utility of the catalysts was demonstrated by a diverse range of amides, obtained from alcohols and nitriles, in moderate to good yields. Biomass derived platform alcohols, such as 5-HMF and furfuryl alcohol, were also tested as potential building blocks for the synthesis of biopolymers. The SO 3 H-catalysts revealed to be a highly efficient and environmentally friendly alternative to the conventional acid catalysts commonly used in the Ritter reaction.

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Section: Resultssupporting

confidence: 88%

“…The catalysts were previously characterized from different Techniques, [21–23] and the main physical‐chemical properties are presented in SI, Table S1 (adapted [25] ). The catalysts K10‐CSP and MWCNTs‐CSP present the highest specific surface area (S BET ), 155 and 181 m 2 /g, respectively.…”

Section: Resultsmentioning

confidence: 99%

Sulfonic Acid‐Functionalized (Bio)Materials as Catalysts for Efficient Amide Bond Synthesis

et al. 2023

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“…[19,20] Among several other tandem Ritter reactions reported, Prins-Ritter reaction is extensively studied, wherein Prins cyclisation followed by Ritter reaction is applied for the efficient synthesis of amide substituted tetrahydropyrans. [21][22][23] Further in a recent study, Prins-Ritter reaction of cyclobutene alcohols produced complex diastereoselective tricyclic amide derivatives. [24] Henry-Ritter reactions are reported to access one pot synthesis of N-(β-Nitro) amides from aldehyde, nitro compounds and nitriles.…”

Section: Introductionmentioning

confidence: 94%

“…Schmidt‐Ritter Reaction converts aldehyde to nitrile which intern reacts with carbocation to produce the desired amide in single step [19,20] . Among several other tandem Ritter reactions reported, Prins‐Ritter reaction is extensively studied, wherein Prins cyclisation followed by Ritter reaction is applied for the efficient synthesis of amide substituted tetrahydropyrans [21–23] . Further in a recent study, Prins‐Ritter reaction of cyclobutene alcohols produced complex diastereoselective tricyclic amide derivatives [24] .…”

Section: Introductionmentioning

confidence: 99%

Acid Catalyzed Multicomponent Reaction to Access Functionalized N‐Benzhydryl Amides: A Tandem Ritter Reaction

Karu,

Malapaka

2023

Eur J Org Chem

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Acid catalyzed multicomponent reaction (MCR) for the synthesis of N‐benzhydryl amide derivatives from aldehydes, N,N‐disubstituted arylamines and nitriles is reported. The reaction is compatible with electronically differentiating aryl/heteroaryl aldehydes/acetals, different nucleophiles (cyclic and acyclic N,N‐disubstituted arylamines,β‐naphthols, 1,3 dicarbonyl, 1,3,5‐trimethoxy benzene), alkyl nitriles, aryl/heteroaryl nitriles in catalytic TFA/TfOH through tandem Ritter reaction. The one‐pot MCR with broad substrate scope generated a wide variety of sterically hindered N‐substituted amides and is successfully applied for the synthesis of isoindolinone.

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Chiral N-(dialkyloctahydro-2H-chromen-4-yl)acetamides: synthesis and analgesic activity

Li-Zhulanov,

Kuznetsova,

Gatilov

et al. 2023

Russ Chem Bull

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Brønsted acid catalyzed Prins-Ritter reaction for selective synthesis of terpenoid-derived 4-amidotetrahydropyran compounds

Cited by 11 publications

References 51 publications

Sulfonic Acid‐Functionalized (Bio)Materials as Catalysts for Efficient Amide Bond Synthesis

Sulfonic Acid‐Functionalized (Bio)Materials as Catalysts for Efficient Amide Bond Synthesis

Acid Catalyzed Multicomponent Reaction to Access Functionalized N‐Benzhydryl Amides: A Tandem Ritter Reaction

Chiral N-(dialkyloctahydro-2H-chromen-4-yl)acetamides: synthesis and analgesic activity

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