Synthesis of highly-functionalised pyridines via hetero-Diels–Alder methodology: reaction of 3-siloxy-1-aza-1,3-butadienes with electron deficient acetylenes

Fletcher, Matthew D.; Hurst, Timothy E.; Miles, Timothy J.; Moody, Christopher J.

doi:10.1016/j.tet.2006.03.051

Cited by 64 publications

(27 citation statements)

References 34 publications

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“…Fletcher et al obtained a set of highly functionalized pyridines via MW-assisted hetero-Diels-Alder methodology involving 3-silyloxy-1-aza-1,3-butadienes with electron-deficient acetylenes [101]. The reactivity of a range of α, β-unsaturated oximes (268) and hydrazones (269) was assessed in the synthesis of tri-and tetra-substituted pyridines bearing an oxygen functionality at C3 [Eq.…”

Section: Intermolecular Hetero-diels-alder Reactionsmentioning

confidence: 99%

Microwave‐Assisted Cycloaddition Reactions

Bougrin

Benhida

2012

Microwaves in Organic Synthesis

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Section: Intermolecular Hetero-diels-alder Reactionsmentioning

confidence: 99%

Microwave‐Assisted Cycloaddition Reactions

Bougrin

Benhida

2012

Microwaves in Organic Synthesis

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“…[91] A series of oxime-or hydrazone-based 3-siloxy-1-azabutadienes underwent hetero-Diels-Alder reactions with electron-deficient alkynes to give 3-siloxypyridines (Scheme 26). Although the yields are modest, the starting Diels-Alder components are readily available and the reaction provides a very rapid entry into 2,3,5,6-tetrasubstituted pyridines bearing oxygen substituents at C-3.…”

Section: Synthesis Of the Pyridine Ringmentioning

confidence: 99%

From Amino Acids to Heteroaromatics—Thiopeptide Antibiotics, Nature's Heterocyclic Peptides

2007

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Amino acids, the building blocks of proteins, also serve as precursors to a wide range of other naturally occurring substances including alkaloids, antibiotics, and, the subject of this Review, heterocyclic peptides. Simple alpha-amino acids are converted into complex arrays of heteroaromatic rings that display interesting and potent biological activity. The thiopeptide antibiotics, with their complex molecular architectures, are wonderful examples. In this Review we show how organic chemists have developed innovative methods for the synthesis of the heterocyclic ring systems, including routes inspired by the likely biosynthetic processes, and successfully assembled such building blocks into the final target molecule by application of orthogonal protecting groups and coupling methodologies.

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“…The pyridine dicarbonitrile substructure was therefore chosen as a basic structural scaffold for the design of a reaction-based library [7]. Thus, the synthesis of highly substituted pyridines has attracted much attention, and a number of procedures have been developed using a variety of protocols, such as hetero-Diels-Alder reaction of 3-siloxy-1-aza-1,3-butadienes with electron-deficient acetylenes [8], three-component condensation of aldehyde, malononitrile, and thiol [9], ruthenium-catalyzed cycloisomerization of 3-azadienynes [10], Mannich reaction of aldehydes and iminium salts [11] and Vilsmeier-Haack reaction of Rhydroxyketenedithioacetals [12]. Among these, one of the very convenient approaches which attracted our attention is the three-component condensation of aldehyde, malononitrile, and thiol to the highly substituted pyridines developed by Evdokimov et al [9].…”

Section: Introductionmentioning

confidence: 99%