Sequential Morita–Baylis–Hillman/Achmatowicz reactions: an expeditious access to pyran-3(6H)-ones with a unique substitution pattern

Guidotti, Bruno Boni; Coelho, Fernando

doi:10.1016/j.tetlet.2015.09.120

Cited by 6 publications

(4 citation statements)

References 84 publications

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“…The characterization data and spectra are supplied as supplementary information (Figure S1–Figure S67) available with this manuscript. The characterization data of 1(a – c) and 2(a – c) matched with published literature [22,24,29] …”

Section: Resultssupporting

confidence: 70%

“…The characterization data of 1(a-c) and 2(a-c) matched with published literature. [22,24,29] Reaction conditions: DABCO (1 eq. ), methyl acrylate (2.5 eq.…”

Section: Resultsmentioning

confidence: 99%

“…[22,23] The MBH adducts of furanics with acrylates have been used as a molecular scaffold to synthesize novel pyran-3(6H)-ones that are present in various bioactive natural products. [24] However, the systematic synthesis of the MBH adducts of 5-substituted-2furaldehydes, renewably prepared from biomass-derived hexose sugars and polymeric carbohydrates, has never been attempted. A systematic study of MBH reaction involving 5-substituted-2furaldehydes will help to understand their reactivity patterns better and expand their derivative chemistry.…”

Section: Introductionmentioning

confidence: 99%

“…Interestingly, the adducts between HMF or FUR with acrylates have been reported to demonstrate the substrate scope during methodology developments of MBH reaction [22,23] . The MBH adducts of furanics with acrylates have been used as a molecular scaffold to synthesize novel pyran‐3(6H)‐ones that are present in various bioactive natural products [24] . However, the systematic synthesis of the MBH adducts of 5‐substituted‐2‐furaldehydes, renewably prepared from biomass‐derived hexose sugars and polymeric carbohydrates, has never been attempted.…”

Section: Introductionmentioning

confidence: 99%

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Renewable synthesis of novel acrylates from biomass‐derived 5‐substituted‐2‐furaldehydes by Morita‐Baylis‐Hillman reaction

Anchan

Dutta

2023

ChemistrySelect

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Biomass‐derived furfurals are becoming increasingly popular as renewable chemical building blocks for synthesizing specialty chemicals. Morita‐Baylis‐Hillman (MBH) reaction is a classic carbon‐carbon bond‐forming transformation between the α‐position of an activated alkene and a carbon electrophile (e. g., aldehyde) using a nucleophilic catalyst, such as a tertiary amine or phosphine. The MBH reaction is highly atom economical, affords excellent yields of adducts under mild reaction conditions, introduces substantial molecular complexity, and enjoys broad substrate scope. In this work, several novel MBH adducts have been synthesized starting from biomass‐derived 5‐substituted‐2‐furaldehydes and acrylates using 1,4‐diazabicyclo[2.2.2]octane (DABCO) as the organocatalyst. This work reports the first systematic study of the MBH reaction of 5‐substituted‐2‐furaldehydes and acrylates. A general synthetic protocol for the high‐yielding synthesis of MBH adducts has been developed. The reactions were performed at room temperature under solvent‐free conditions, and the spectroscopically pure products were produced in good to excellent isolated yields. Moreover, DABCO was recovered from the reaction mixture and successfully recycled.

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Section: Resultssupporting

confidence: 70%

“…The characterization data of 1(a-c) and 2(a-c) matched with published literature. [22,24,29] Reaction conditions: DABCO (1 eq. ), methyl acrylate (2.5 eq.…”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Renewable synthesis of novel acrylates from biomass‐derived 5‐substituted‐2‐furaldehydes by Morita‐Baylis‐Hillman reaction

Anchan

Dutta

2023

ChemistrySelect

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ChemInform Abstract: Sequential Morita—Baylis—Hillman/Achmatowicz Reactions: An Expeditious Access to Pyran‐3(6H)‐ones with a Unique Substitution Pattern.

Guidotti

Coelho

2016

ChemInform

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Baylis–Hillman Acetates in Synthesis: Copper(I)/tert‐Butyl Hydroperoxide Promoted One‐Pot Oxidative Intramolecular Cyclization Protocol for the Preparation of Pyrrole‐Fused Compounds and the Formal Synthesis of (±)‐Crispine A

et al. 2016

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A convenient one‐pot protocol for the synthesis of benzo‐fused and indole‐fused indolizines from Baylis–Hillman acetates was developed. This strategy involves CuBr/tert‐butyl hydroperoxide promoted oxidation, intramolecular cyclization, and aromatization as key steps. The efficacy of this methodology was demonstrated by the formal synthesis of (±)‐crispine A, a biologically active molecule.

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Sequential Morita–Baylis–Hillman/Achmatowicz reactions: an expeditious access to pyran-3(6H)-ones with a unique substitution pattern

Cited by 6 publications

References 84 publications

Renewable synthesis of novel acrylates from biomass‐derived 5‐substituted‐2‐furaldehydes by Morita‐Baylis‐Hillman reaction

Renewable synthesis of novel acrylates from biomass‐derived 5‐substituted‐2‐furaldehydes by Morita‐Baylis‐Hillman reaction

ChemInform Abstract: Sequential Morita—Baylis—Hillman/Achmatowicz Reactions: An Expeditious Access to Pyran‐3(6H)‐ones with a Unique Substitution Pattern.

Baylis–Hillman Acetates in Synthesis: Copper(I)/tert‐Butyl Hydroperoxide Promoted One‐Pot Oxidative Intramolecular Cyclization Protocol for the Preparation of Pyrrole‐Fused Compounds and the Formal Synthesis of (±)‐Crispine A

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