One-pot synthesis of 5-oxopyrrolidine-2-carboxamides via a tandem Ugi 4CC/SN cyclization starting from Baylis–Hillman bromides

Zeng, Xiao‐Hua; Wang, Hongmei; Wu, Lei; Ding, Ming‐Wu

doi:10.1016/j.tet.2013.03.058

Cited by 22 publications

(20 citation statements)

References 36 publications

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“…In this way, although Passerini adduct 7a was obtained with a high yield, Ugi adduct 8 could not be isolated, since a spontaneous cyclization took place yielding γ-lactame 9 (Scheme 3). This is the result of an intramolecular nucleophilic substitution, because of the nucleophilic character of the α carbon on the enol tautomer, as previously reported [18,19].…”

Section: Reactivity Of Keto and Enol Tautomerssupporting

confidence: 67%

“…Supplementary Materials: The following are available online at: 1 H, 19 F, 13 C, DEPT-135 NMR spectra and high-resolution mass spectra of the compounds, and X-ray crystallographic files in CIF format for compounds 5 (CCDC 2052029), 6 (CCDC 2052030), 9 (CCDC 2052031), 11b (CCDC 2052027) and 12c (CCDC 2052028).…”

Section: Discussionmentioning

confidence: 99%

“…Melting points were not corrected. 1 H, 19 F and 13 C NMR spectra were recorded in CDCl 3 , CD 3 CN or DMSO-d 6 on Varian Mercury Plus 300 (at 300 and 75 MHz, respectively) or Varian Unity Inova 400 (at 400 and 100 MHz, respectively) spectrometers (Varian, Inc., Palo Alto, United States of America); DEPT-135 experiments were performed to assign carbon-13 signals. Chemical shifts are reported in parts per million with respect to residual solvent protons and coupling constants in hertz.…”

Section: General Methodsmentioning

confidence: 99%

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Keto-Enol Tautomerism in Passerini and Ugi Adducts

et al. 2021

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The use of arylglyoxal as starting material in Passerini and Ugi reactions affords β-ketoamides. This has allowed to study keto-enol tautomerism in these systems and assess the way in which the presence of acyloxy or aminoacyl groups bound to the C2 position affects such tautomerism, and to investigate the reactivity of both the enol and carbonyl forms. In this work we also prove the versatility of the Passerini reaction, since depending on the conditions to which the corresponding adducts are subjected different products of synthetic interest can be obtained.

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Section: Reactivity Of Keto and Enol Tautomerssupporting

confidence: 67%

Section: Discussionmentioning

confidence: 99%

Section: General Methodsmentioning

confidence: 99%

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Keto-Enol Tautomerism in Passerini and Ugi Adducts

et al. 2021

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“…We have previously synthesized 2-aroyl-4-arylidene-5-oxopyrrolidines via tandem Ugi and cyclization reactions (see Figure 1) 16 and found they are biological isochores of Rhopaladins because of the five-membered nitrogen heterocycles with arylidene and aroyl groups. In order to study the anti-cervical cancer activity of these compounds, we decided to synthesize fluorine-containing ( E )-2-aroyl-4-(4-fluorobenzylidene)-5-oxopyrrolidines.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and cytotoxic effects on HeLa cervical cancer cells of (E)-2-aroyl-4-(4-fluorobenzylidene)-5-oxopyrrolidine

Wang

Zhu

Shou-heng

et al. 2020

Journal of Chemical Research

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Seven ( E)-2-aroyl-4-(4-fluorobenzylidene)-5-oxopyrrolidines were synthesized via a tandem Ugi 4CC/SN cyclization sequence starting from a Baylis-Hillman-derived acid, primary amines, arylglyoxals, and isocyanides in one pot. In addition, the cytotoxicity of these compounds on the cervical cancer cell line HeLa was studied by MTT assay. The results showed that most of the compounds could inhibit the proliferation of HeLa cells significantly.

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“…Ding and coworkers in 2013 reported the construction of 5‐oxopyrrolidine‐2‐carboxamides 31 via a tandem Ugi 4CC/S N cyclization strategy (Scheme 9). [44] Baylis‐Hillman bromides, primary amines, isocyanides, and arylglyoxals were used in Ugi condensation, followed by intramolecular substitution to afford 5‐oxopyrrolidine‐2‐carboxamides 31 in good‐to‐excellent yields.…”

Section: Base‐mediated Post‐ugi Transformationsmentioning

confidence: 99%

Advances in Base‐Mediated Post‐Ugi Transformations via Peptidyl Anion Trapping

et al. 2021

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Advances in base‐mediated post‐Ugi transformations are reported and discussed. The minireview encompasses reports showing the abstraction of an alpha proton adjacent to amide carbonyl in aldehyde‐derived Ugi adducts under basic conditions to perform intramolecular and intermolecular cyclizations. The methodologies have been broadly classified depending on the peptidyl anion trapping under metal‐free, metal‐catalyzed, microwave‐assisted, and external electrophile‐aided reaction conditions. A comprehensive analysis of the methods has been presented, highlighting the importance in synthetic and medicinal chemistry.

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One-pot synthesis of 5-oxopyrrolidine-2-carboxamides via a tandem Ugi 4CC/SN cyclization starting from Baylis–Hillman bromides

Cited by 22 publications

References 36 publications

Keto-Enol Tautomerism in Passerini and Ugi Adducts

Keto-Enol Tautomerism in Passerini and Ugi Adducts

Synthesis and cytotoxic effects on HeLa cervical cancer cells of (E)-2-aroyl-4-(4-fluorobenzylidene)-5-oxopyrrolidine

Advances in Base‐Mediated Post‐Ugi Transformations via Peptidyl Anion Trapping

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