Synthesis of 4-ylidenebutenolides and 4-oxo-2-enoic acid methyl esters from 5-methoxy-2-furyl carbinols

D’Auria, Maurizio; Piancatelli, Giovanni; Scettri, Arrigo

doi:10.1016/0040-4020(80)88034-3

Cited by 19 publications

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“…Moreover, 5-nitro-2-furyl-derivatives result in no reaction even under harsh conditions, while the 5-methoxy and 5-chloro-2-furylcarbinols lead to the formation of 4-ylidenebutenolides [16][17][18].…”

Section: An Overview Of the Piancatelli Rearrangementmentioning

confidence: 99%

The Piancatelli Rearrangement: New Applications for an Intriguing Reaction

2013

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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 recently, including developments of the Piancatelli rearrangement with some interesting inter-and intramolecular variants. This review will mainly focus on the general aspects of the reaction along with its more recent applications.

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Section: An Overview Of the Piancatelli Rearrangementmentioning

confidence: 99%

The Piancatelli Rearrangement: New Applications for an Intriguing Reaction

2013

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“…This confirms that furan is the intermediate in both transformations. When a similar Lewis acid-mediated reaction is performed in DCM : H 2 O (3 : 1), butenolide 5e is formed exclusively instead of Piancatelli rearrangement product 7 , 13 which indicates that the ethyl group is eliminated via S N 2 attack by the nucleophile on the ethyl group rather than an addition–elimination mechanism (see Page S37 in the ESI†).…”

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confidence: 99%