A Thermally Induced Hydride Transfer from an Amine to an Allene Triggers an Annulation Reaction, Giving Dihydrofuropyridinones

Abstract2‐Propargyl alcohols are widely used in organic reactions. Their great success is rooted in the presence of multiple functional groups. This review will focus on six types of mechanisms: (i) 2‐propargyl alcohols as carbocation precursors, (ii) alkynes as electrophiles, (iii) alcohols as nucleophiles, (iv) fracture via ketones or elimination into alkene intermediates, (v) oxidation into alkynyl‐ortho‐quinone methides or carbonyl intermediates, and (vi) ring expansions. Reactions involving alkanes, alkenes, alkynes, arenes, alcohols, amines, amides, ketones, CO2, hydrazine, iodobenzene, azides, carbenes, arylboronic acids, etc. will be discussed. We hope that this review will help to promote future research in this area.magnified image

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2‐Propargyl Alcohols in Organic Synthesis

Qian

Huang

et al. 2019

Adv Synth Catal

139

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Convenient Access to 2,3‐Disubstituted‐cyclobut‐2‐en‐1‐ones under Suzuki Conditions and Their Synthetic Utility

Alcaide

Almendros

Lázaro‐Milla

2019

Chemistry A European J

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A regioselective synthesis of general applicability has been designed for the one‐pot preparation of 2,3‐disubstituted‐cyclobutenones from iodoalkynes through cyclobutenylation, Suzuki CC coupling, and ketone formation. This one‐pot methodology has been applied to the selective synthesis of an orally active cyclooxygenase II inhibitor. Furthermore, the obtained cyclobut‐2‐en‐1‐ones were used as synthons in several transformations, such as, the preparation of β‐lactams, phthalazines, cyclohexa‐2,5‐dien‐1‐ones, and cyclopent‐3‐en‐1‐ones.

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Redox-Neutral Cascade Dearomatization of Indoles via Hydride Transfer: Divergent Synthesis of Tetrahydroquinoline-Fused Spiroindolenines

Shen

Xiao

et al. 2019

J. Org. Chem.

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The redox-neutral cascade dearomatization of indoles with o-aminobenzaldehydes has been realized via the hydride transfer strategy, achieving the condition-and substrate-controlled divergent synthesis of tetrahydroquinoline-fused spiroindolenines. The integration of hydride transfer-involved C(sp 3 )−H functionalization with dearomatization provides a promising platform for the construction of structurally diverse molecules.

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A Thermally Induced Hydride Transfer from an Amine to an Allene Triggers an Annulation Reaction, Giving Dihydrofuropyridinones

Abstract: A thermal rearrangement leading to dihydrofuropyridinones and related polycyclic ring systems from furanones and cyclobutenones is described. A key feature of the reaction is the thermally induced hydride transfer from a 3°-amine to a conjugated allene to trigger cyclization.

Cited by 9 publications

References 62 publications

2‐Propargyl Alcohols in Organic Synthesis

2‐Propargyl Alcohols in Organic Synthesis

Convenient Access to 2,3‐Disubstituted‐cyclobut‐2‐en‐1‐ones under Suzuki Conditions and Their Synthetic Utility

Redox-Neutral Cascade Dearomatization of Indoles via Hydride Transfer: Divergent Synthesis of Tetrahydroquinoline-Fused Spiroindolenines

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