Tandem Reaction Progress Analysis as a Means for Dissecting Catalytic Reactions: Application to the Aza-Piancatelli Rearrangement
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چکیده
منابع مشابه
The Piancatelli rearrangement: new applications for an intriguing reaction.
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 s...
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Well-represented in natural products and biologically active molecules, the cyclopentenone scaffold has long been an inspiration for the development of new methodologies. In 1976, Piancatelli and co-workers reported a new method for the synthesis of 4-hydroxycyclopentenone derivatives by an acid-catalyzed rearrangement of suitable 2-furylcarbinols (Scheme 1). The overall transformation is belie...
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2-Furylcarbinols undergo a smooth aza-Piancatelli rearrangement followed by Friedel-Crafts alkylation with a bifunctional substrate, (1H-pyrrol-1-yl)aniline, in the presence of 10 mol% In(OTf)3 in acetonitrile at room temperature to afford the corresponding hexahydrobenzo[b]cyclopenta[f]pyrrolo[1,2-d][1,4]diazepin-11(4aH)-one scaffolds in good yields. This method offers significant advantages s...
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number of elegant approaches to construct azaspirocycles have been developed. The methods differ in the strategy used to address the two main synthetic challenges: construction of the tertiary carbon center bearing the nitrogen atom, and the formation of the spirocyclic ring system. Generally, the synthetic routes rely on a two-step process where the tertiary carbon center and the spirocycle ar...
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ژورنال
عنوان ژورنال: ACS Catalysis
سال: 2015
ISSN: 2155-5435,2155-5435
DOI: 10.1021/acscatal.5b01087