2013
DOI: 10.3390/molecules181012290
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The Piancatelli Rearrangement: New Applications for an Intriguing Reaction

Abstract: Nearly forty years ago, at the University of Rome, Giovanni Piancatelli and co-workers discovered the acid-catalyzed water-mediated rearrangement of 2-furylcarbinols into 4-hydroxycyclopentenones. These motifs are core components of several pharmacologically active compounds and precursors of many natural products. The main features of this reaction are the simple experimental conditions, the stereochemical outcome and the generality of the procedure. Consequently, a re-emergence of this reaction has been seen… Show more

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Cited by 112 publications
(49 citation statements)
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“…Hydrogenation-decarbonylation of furfural to furan compounds (i.e.,m ethyl furan, dimethyl furan), [18,19] ring rearrangement of furfural to cyclopentanone (CPO) through the Piancatelli reaction, [20][21][22] or oxidation of furfural to carboxylic acids [23,24] are outstanding examples of furfural conversion into more stable forms that have been recently reported in the literature. In the so-called Sylvan process, methyl furan is condensed with different types of carbonyl compounds, such as acetone, butanal, or furfural, [25,26] to elongate the carbon chain and bring the products to the fuel range.…”
Section: Introductionmentioning
confidence: 99%
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“…Hydrogenation-decarbonylation of furfural to furan compounds (i.e.,m ethyl furan, dimethyl furan), [18,19] ring rearrangement of furfural to cyclopentanone (CPO) through the Piancatelli reaction, [20][21][22] or oxidation of furfural to carboxylic acids [23,24] are outstanding examples of furfural conversion into more stable forms that have been recently reported in the literature. In the so-called Sylvan process, methyl furan is condensed with different types of carbonyl compounds, such as acetone, butanal, or furfural, [25,26] to elongate the carbon chain and bring the products to the fuel range.…”
Section: Introductionmentioning
confidence: 99%
“…[29] Although the Piancatelli ring rearrangemento ff urfuryl alcoholr eadily occurs in hot liquid water withoutt he need for an additional catalyst, hydrogenation is required to first hydrogenate the CO group in furfural, as well as the resulting C=Cd ouble bond after the ring closure to obtain CPO. [20,22,30] Moreover,t he presence of acetic acid in the reaction mixture provides ap ositive effect on the yield of the desired products. [31,32] For example,o ver 75 %y ield of CPO has been reported over Pt/C or Ni/CNTs( carbon nanotubes).…”
Section: Introductionmentioning
confidence: 99%
“…[4] This transformation is based on the rearrangement of 2-furylcarbinols to furnish the corresponding4 -hydroxycyclopentenones and has become am ethodo fc hoice to access the framework of prostaglandind erivatives (Scheme 1). [5] However,t his reaction was essentially limitedt ot he use of water as an ucleophile until the last decade, in whichasurge of publications revealed its wide synthetic utility by extending the scope of the nucleophiles. [5b, 6] For instance, the group of Read de Alaniz reported, in 2010, an elegantd ysprosium(III)-catalyzed aza-Piancatellic yclization to generate 4-aminocyclopentenones, [6a] the framework of which can be found in complex bioactive molecules such as pactamycin.…”
Section: Introductionmentioning
confidence: 99%
“…This reaction has initially been reported by Piancatelli et al (Piutti & Quartieri, 2013) upon observing the ring rearrangement of 2-furylcarbinol in an acidic aqueous system and has subsequently been referred as a Piancatelli rearrangement. Basically, the ring rearrangement step does not need catalyst, just water and proper temperature to promote the water self-dissociation.…”
Section: Pino Hincapié and Lópezmentioning
confidence: 71%