Upgrading furanic platforms to α-enaminones: tunable continuous flow hydrogenation of bio-based cyclopentenones

Here we describe a tunable continuous flow hydrogenation of trans -4,5-diamino cyclopentenones (DCPs) allowing the selective stepwise synthesis of novel bifunctionalized cyclopentanones (up to 96% yield and >92% selectivity). Stability studies of the diamino cyclopentanone motif led to the develo...

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Bibliographic Details
Published in:Reaction chemistry & engineering 2023-01, Vol.8 (2), p.482-489
Main Authors: Cavaca, Lídia A. S, Coelho, Jaime A. S, Lucas, Susana D, Loureiro, Rui M. S, Gomes, Rafael F. A, Afonso, Carlos A. M
Format: Article
Language:English
Subjects:
Continuous flow
Cyclopentene
Deuteration
Furfural
Hydrogenation
Selectivity
Synthesis
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Summary:Here we describe a tunable continuous flow hydrogenation of trans -4,5-diamino cyclopentenones (DCPs) allowing the selective stepwise synthesis of novel bifunctionalized cyclopentanones (up to 96% yield and >92% selectivity). Stability studies of the diamino cyclopentanone motif led to the development of an elimination procedure yielding the corresponding α-enaminones in good yields. Deuteration of the cyclopentene scaffold can also be performed using D 2 O as a source of D 2 . A sequential process for the synthesis of α-enaminones directly from furfural is also described. The methodology allows the preparation of a previously reported ATP-sensitive potassium channel agonist in 71% yield. Continuous flow hydrogenation of trans- 4,5-diamino cyclopentenones to diamino cyclopentanones and base-promoted elimination originates α-enaminones. The strategy is applied to the short synthesis of reported ATP-sensitive potassium channel agonist.
ISSN:2058-9883
2058-9883
DOI:10.1039/d2re00292b