Synthesis of cucurbitine derivatives: facile straightforward approach to methyl 3-amino-4-aryl-1-methylpyrrolydine-3-carboxylates

trans-4,5-Diamino-cyclopent-2-enones (CP) are usually prepared by Lewis acid-catalyzed condensation of furfural and a secondary amine in an organic solvent. The reaction proceeds through the formation of a Stenhouse salt (SS) intermediate followed by an electrocyclization reaction to afford the desired CP. Herein, we described the use of Cu(OTf) as a very efficient catalyst for the synthesis of CP in water at room temperature. Furthermore, the mild reaction conditions, catalyst reusability, and outstanding functional group tolerance suggest that this CP platform can be further used in chemical biology.

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“…The product was isolated in quantitative yield (178 mg) and 93% purity as a brown oil. The spectral data are in agreement with the literature …”

Section: Methodssupporting

confidence: 91%

Copper(II) Triflate As a Reusable Catalyst for the Synthesis of trans-4,5-Diamino-cyclopent-2-enones in Water

et al. 2018

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“…The Schiff bases synthesized (1a, [16] 1b, [17] 1c, [16] 1d, [16] 1e, [18] 1f, [19] 1g, [20] 1h, [21] 1i, [22] 1j, [23] 1k, [23] and 1l) [24] are known, and their characterization data were in agreement with those reported in literature.…”

Section: Methodssupporting

confidence: 88%

Stereoselective Synthesis of α‐Alkylidene β‐Oxo Amides by Palladium‐Catalyzed Carbonylation

et al. 2014

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A direct method to obtain α‐alkylidene β‐oxo amides by the palladium‐catalyzed carbonylation of α‐chloro ketones in the presence of aromatic imines has been described. The methodology can be applied to a variety of C‐aryl imines bearing N‐aryl or N‐alkyl substituents. The entire process is highly stereoselective and affords the α‐alkylidene β‐oxo amides only as (Z) isomers. A mechanistic hypothesis involving an acyl‐β‐lactam intermediate has also been proposed.

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“…This reaction is an important method for the formation of pyrrolidines [ 26 ] and has been used in the synthesis of natural products [ 27 , 28 ]. Among the vast number of procedures for making azomethine ylides [ 29 , 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 ], the decarboxylative condensation of α-amino acids with aldehydes, typically heated in toluene or DMF, was chosen [ 42 ]. Thus, the reaction of paraformaldehyde and sarcosine ( N -methylglycine) in refluxing toluene in the presence of the 2-cyanoacrylates 8 cleanly provided the desired pyrrolidines 7 , containing the 2-arylethyl amine motif ( Table 2 ).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Dihydrouracils Spiro-Fused to Pyrrolidines: Druglike Molecules Based on the 2-Arylethyl Amine Scaffold

et al. 2010

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The synthesis of a small library of dihydrouracils spiro-fused to pyrrolidines is described. These compounds are synthesized from β-aryl pyrrolidines, providing products with the 2-arylethyl amine moiety, a structural feature often encountered in compounds active in the central nervous system. The β-aryl pyrrolidines are synthesized through a three-step methodology that includes a Knoevenagel condensation reaction, a 1,3-dipolar cycloaddition reaction, and a nitrile reduction.

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Synthesis of cucurbitine derivatives: facile straightforward approach to methyl 3-amino-4-aryl-1-methylpyrrolydine-3-carboxylates

Cited by 35 publications

References 21 publications

Copper(II) Triflate As a Reusable Catalyst for the Synthesis of trans-4,5-Diamino-cyclopent-2-enones in Water

Copper(II) Triflate As a Reusable Catalyst for the Synthesis of trans-4,5-Diamino-cyclopent-2-enones in Water

Stereoselective Synthesis of α‐Alkylidene β‐Oxo Amides by Palladium‐Catalyzed Carbonylation

Synthesis of Dihydrouracils Spiro-Fused to Pyrrolidines: Druglike Molecules Based on the 2-Arylethyl Amine Scaffold

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