CeCl3·7H2O/AcCl-catalyzed Prins–Ritter reaction sequence: a novel synthesis of 4-amido tetrahydropyran derivatives

Yadav, J. S.; Reddy, B. V. Subba; Kumar, G. G. K. S. Narayana; Reddy, G. Madhusudhan

doi:10.1016/j.tetlet.2007.05.056

Cited by 72 publications

(22 citation statements)

References 26 publications

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“…1 H-NMR and silica gel Acquired 1 H, 13 C NMR and FT IR spectral data of obtained products were in accordance with published one [36].…”

Section: Experimental Section Materialssupporting

confidence: 81%

“…We verified the both model synthetic procedures with published catalysts according to the general procedure published in the articles [35,36]. Syntheses were then carried out with Ce(III) supported on above described resin and the results were compared in terms of the reaction time and the yield relative to the used catalytic system.…”

Section: Resultsmentioning

confidence: 98%

“…Catalytic system used in this case featured the 10 mol% of cerium trichloride heptahydrate CeCl 3 .7H 2 O. The second model synthesis was domino synthesis of 4-amidotetrahydropyrane derivatives published previously in [36], where 5 mol% of CeCl 3 .7H 2 O was used as a catalyst.…”

Section: Resultsmentioning

confidence: 99%

“…General procedure for preparation of 4-amidotetrahydropyranes [36]: A mixture of 1.2 mmol of but-3-en-1-ol, 1 mmol of 4-X-benzaldehyde, and 1.5 mmol of acetyl chloride, in role of activator for Prins-Ritter domino synthesis [36], with 0.05 mmol of appropriate catalytic system (Table 2) in 5 mL of acetonitrile as a solvent and nucleophilic reagent, was stirred at room temperature until disappearance of carbonyl compound from the reaction mixture. The reaction was monitored by TLC.…”

Section: General Synthetic Proceduresmentioning

confidence: 99%

“…The combined organic layers were dried with anhydrous Na 2 SO 4 and purified with Figure 2, for mechanism detail the ref. [36]). The electron effect of substituent X in the used 4-X-benzaldehydes on the reaction results was the same as described above for α-aminophosphonate formation.…”

Section: General Synthetic Proceduresmentioning

confidence: 99%

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Kabachnik-Fields and Prins- Ritter Synthesis: Application of Ce(III) Supported on a Weakly Acidic Cation-exchanger Resin in Comparative Study

2015

J Chem Appl

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We described results of comparative studies of the application of Ce(III) cation supported on macroporous weakly acidic polyacrylate resin as catalyst in two model three-component domino syntheses, i.e. Kabachnik-Fields domino synthesis of α-aminophosphonates, and Prins-Ritter domino synthesis of 4-amidotetrahydropyrane derivatives, respectively. It was discovered that cation Ce(III) supported on a weak acid macroporous cation-exchanger shown in the studied reactions at least the same or better catalytic activity as salt CeCl3.7H2O, eventually doped by NaI. Further, we found that reactivity of the low reactive 4-methoxybenzaldehyde as carbonyl compounds in the presence of Ce(III) catalyst increases, while the reactivity of the highly reactive 4-nitrobenzaldehyde in this case strongly decreases due to its low coordination with the catalyst. Finally, the presented synthetic protocols using cerium(III) supported on low-cost industrial resin further increases green impact of studied domino syntheses of α-aminophosphonates, and 4-amidotetrahydropyrane derivatives.

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“…1 H-NMR and silica gel Acquired 1 H, 13 C NMR and FT IR spectral data of obtained products were in accordance with published one [36].…”

Section: Experimental Section Materialssupporting

confidence: 81%

Section: Resultsmentioning

confidence: 98%

Section: Resultsmentioning

confidence: 99%

Section: General Synthetic Proceduresmentioning

confidence: 99%

Section: General Synthetic Proceduresmentioning

confidence: 99%

See 3 more Smart Citations

Kabachnik-Fields and Prins- Ritter Synthesis: Application of Ce(III) Supported on a Weakly Acidic Cation-exchanger Resin in Comparative Study

2015

J Chem Appl

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Alcohol as a Reagent in Homogeneous Catalysis

Han

Sun

Xia

et al. 2017

Solvents as Reagents in Organic Synthesis

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Indium(III) Triflate‐Catalyzed Efficient Prins‐Type Cyclization of β‐Allenols and Aldehydes

et al. 2016

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We report here an indium(III) triflate (In(OTf)3)‐catalyzed Prins‐type cyclization of disubstituted β‐allenols in the presence of aldehydes in dichloromethane (CH2Cl2) affording different 3,6‐dihydro‐2H‐pyran at room temperature or 45 °C. The high efficiency of the reaction and easily available nature of the starting materials/catalyst make it useful in synthesizing different dihydropyran derivatives. A rationale for the formation of all the products was proposed.magnified image

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CeCl3·7H2O/AcCl-catalyzed Prins–Ritter reaction sequence: a novel synthesis of 4-amido tetrahydropyran derivatives

Cited by 72 publications

References 26 publications

Kabachnik-Fields and Prins- Ritter Synthesis: Application of Ce(III) Supported on a Weakly Acidic Cation-exchanger Resin in Comparative Study

Kabachnik-Fields and Prins- Ritter Synthesis: Application of Ce(III) Supported on a Weakly Acidic Cation-exchanger Resin in Comparative Study

Alcohol as a Reagent in Homogeneous Catalysis

Indium(III) Triflate‐Catalyzed Efficient Prins‐Type Cyclization of β‐Allenols and Aldehydes

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