Synthesis of multisubstituted pyrroles by ligand-controlled site-selective arylation and their transformation into multiarylated pyrrolines and pyrrolidines

Yamaguchi, Miyuki; Fujiwara, Sakiko; Mori, Yoshio; Konishi, Hideyuki; Manabe, Kei

doi:10.1016/j.tet.2022.132962

Cited by 6 publications

(2 citation statements)

References 80 publications

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“…The nonaromatic 2 H -pyrrole ring is an important heterocyclic system encountered in natural products and is also used as a valuable intermediate in organic synthesis . There are several strategies for the preparation of 2 H -pyrroles including dearomatization of 1 H -pyrroles, transformations of other pyrrole and azole derivatives, cycloaddition reactions of alkynes with isocyanides, and cyclization of alkynylated enaminones .…”

Section: Resultsmentioning

confidence: 99%

Stable 2-Azaallyl Salts as a Bridge between 2H-Azirines and Densely Functionalized 2H-Pyrroles

Pavlenko,

Agafonova,

Sakharov

et al. 2024

J. Org. Chem.

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An efficient protocol for the synthesis of stable 2azaallyl anion salts by the reaction of alkyl 2-bromo-2H-azirine-2carboxylates with trimethylsilyl cyanide/Bu 4 NF has been developed. The domino reaction proceeds in four steps via the cleavage of the azirine C−C bond to provide the tetrabutylammonium salts of stereochemically pure 2-azaallyl anions having U-configuration relative to the cyano groups. The anions with an ortho-substituted aryl group or styryl group exist as a mixture of two geometrical isomers across the N2−C3 bond. 2-Azaallyl anion salts have been shown to be convenient substrates for the one-pot synthesis of densely functionalized 2H-pyrroles by the alkylation−cyclization sequence.

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Section: Resultsmentioning

confidence: 99%

Stable 2-Azaallyl Salts as a Bridge between 2H-Azirines and Densely Functionalized 2H-Pyrroles

Pavlenko,

Agafonova,

Sakharov

et al. 2024

J. Org. Chem.

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“…35) If the reactions of chloroarenes are applicable to those of chlorogroup-containing pharmaceuticals, they can have potential synthetic applications in the late-stage derivatization of these compounds. [36][37][38][39] Thus, the reaction with 2 was conducted for pharmaceuticals having a chloroarene moiety (Table 3). The desired products (14)(15)(16)(17) were obtained in moderate to good yields.…”

Section: Resultsmentioning

confidence: 99%

Palladium-Catalyzed C–H Arylation of [1,1′-Biphenyl]-2-ols with Chloroarenes

Kinoshita

Yamaguchi

Sasou

et al. 2023

CHEMICAL & PHARMACEUTICAL BULLETIN

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Palladium-catalyzed, hydroxy-group-directed C-H arylation of [1,1′-biphenyl]-2-ols with chloroarenes was performed. The reaction showed a broad substrate scope and was successfully applied to pharmaceuticals containing a chloro group. Using 2-heteroarylphenols instead of [1,1′-biphenyl]-2-ols also yielded the desired products. The arylated product was further transformed into a triphenylene derivative.

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Recent Advances in Synthetic Methods for 2H‐Pyrroles

Choi,

Kim

2023

Adv Synth Catal

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The compound, 2H‐pyrrole, is a key scaffold contained in natural products, bioactive compounds, pharmaceuticals, and organic functional materials. However, the development of efficient synthetic strategies for 2H‐pyrroles is challenging. This is because 2H‐pyrroles, owing to their nonaromatic nature, are easily converted into the thermodynamically more stable 1H‐pyrroles. Recently, efficient and straightforward synthetic strategies for 2H‐pyrroles have been developed, including the dearomatization of 1H‐pyrrole, oxidation of pyrrolines or pyrrolidines, ring construction via catalytic cycloaddition, and rearrangement of 3H‐pyrroles. In this review, we summarize the progress in the research on 2H‐pyrrole synthesis since 2000 and briefly discuss the synthesis reaction mechanisms.

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Synthesis of multisubstituted pyrroles by ligand-controlled site-selective arylation and their transformation into multiarylated pyrrolines and pyrrolidines

Cited by 6 publications

References 80 publications

Stable 2-Azaallyl Salts as a Bridge between 2H-Azirines and Densely Functionalized 2H-Pyrroles

Stable 2-Azaallyl Salts as a Bridge between 2H-Azirines and Densely Functionalized 2H-Pyrroles

Palladium-Catalyzed C–H Arylation of [1,1′-Biphenyl]-2-ols with Chloroarenes

Recent Advances in Synthetic Methods for 2H‐Pyrroles

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