Thermally-induced intramolecular [2 + 2] cycloaddition of allene-methylenecyclopropanes: expedient access to two separable spiropolycyclic heterocycles

Li, Min; Wei, Yin; Shi, Min

doi:10.1039/d2qo01473d

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2024

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Cited by 4 publications

References 59 publications

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Synthesis of gem‐Difluorocyclobutane‐Fused Indolines via Ruthenium‐Catalyzed Defluorinative Annulation of Trifluoromethyl Carbenoids with 2‐Alkenylanilines

Tan,

Li,

et al. 2024

Adv Synth Catal

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A ruthenium‐catalyzed defluorinative annulation of 2‐alkenylanilines with α‐trifluoromethyl diazoester or diazoketones is described. The reaction has broad substrate scope, affording a range of gem‐difluorocyclobutane‐fused indolines in moderate to good yields with cis‐configuration. Mechanistic investigations indicate that the reaction proceeds through a sequential N‐H insertion/C‐F bond cleavage/[2 + 2] cycloadditon process. α‐Trifluoromethyl‐α‐diazo reagents serve as gem‐difluorinated C2 subunits by cleaving one C‐F bond.

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Synthesis of gem‐Difluorocyclobutane‐Fused Indolines via Ruthenium‐Catalyzed Defluorinative Annulation of Trifluoromethyl Carbenoids with 2‐Alkenylanilines

Tan,

Li,

et al. 2024

Adv Synth Catal

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A New Method of Constructing Methyleneindene and Quinoline Frameworks from Methylenecyclopropanes

Yang,

Shi,

Wei

2024

Chemistry An Asian Journal

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In this paper, we have established an operationally convenient protocol for the rapid construction of polysubstituted methyleneindene and quinoline derivatives under mild conditions. This new synthetic method is achieved through the conversion of acetyl‐substituted methylenecyclopropanes with TsOH·H2O and ortho‐amino‐substituted methylenecyclopropanes with aromatic aldehyde and TsOH·H2O, respectively. A variety of transformations of the obtained products was demonstrated. The plausible reaction mechanisms were also proposed.

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Thermal Cyclobutane Ring Formation

Almendros,

Aragoncillo

2024

Reference Module in Chemistry, Molecular Sciences and Chemical Engineering

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Thermally-induced intramolecular [2 + 2] cycloaddition of allene-methylenecyclopropanes: expedient access to two separable spiropolycyclic heterocycles

Cited by 4 publications

References 59 publications

Synthesis of gem‐Difluorocyclobutane‐Fused Indolines via Ruthenium‐Catalyzed Defluorinative Annulation of Trifluoromethyl Carbenoids with 2‐Alkenylanilines

Synthesis of gem‐Difluorocyclobutane‐Fused Indolines via Ruthenium‐Catalyzed Defluorinative Annulation of Trifluoromethyl Carbenoids with 2‐Alkenylanilines

A New Method of Constructing Methyleneindene and Quinoline Frameworks from Methylenecyclopropanes

Thermal Cyclobutane Ring Formation

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