Eco-friendly, in-water, and catalyst-free assembly of acylethenylpyrroloimidazoindoles from 3<i>H</i>-indoles and acylpyrrolylacetylenes

Oparina, Ludmila A.; Belyaeva, Kseniya V.; Kolyvanov, Nikita A.; Ushakov, Igor A.; Tomilin, Denis N.; Sobenina, Lyubov N.; Kuzmin, Anton V.; Trofimov, Boris A.

doi:10.1039/d3nj05049a

New J. Chem.

2024

DOI: 10.1039/d3nj05049a

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Eco-friendly, in-water, and catalyst-free assembly of acylethenylpyrroloimidazoindoles from 3H-indoles and acylpyrrolylacetylenes

Ludmila A. Oparina,

Kseniya V. Belyaeva,

Nikita A. Kolyvanov

et al.

Abstract: The merging of fundamentally and biologically important heterocyclic structures such as pyrroles, indoles and imidazoles in molecule of dihydropyrrolo[1',2':3,4]imidazo[1,2-a]indoles functionalized by E-acylethenyl groups has been achieved in water on the...

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2024

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Cited by 3 publications

References 26 publications

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Annulation of 1-methylisoquinoline with pyrrolylacetylenic ketones: catalyst-free stereoselective synthesis of (E)-acylethenylpyrrolo[1’,2’:3,4]imidazo[2,1-a]isoquinolines

Belyaeva,

Nikitina,

Saliy

et al. 2024

Mendeleev Communications

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Annulation of 1-methylisoquinoline with pyrrolylacetylenic ketones: catalyst-free stereoselective synthesis of (E)-acylethenylpyrrolo[1’,2’:3,4]imidazo[2,1-a]isoquinolines

Belyaeva,

Nikitina,

Saliy

et al. 2024

Mendeleev Communications

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TEMPO/PhI(OAc)₂ promotes the α-aminophosphinoylation of alcohols with amines and H-phosphine oxides in aqueous medium

Huang,

Jin,

et al. 2024

Org. Biomol. Chem.

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Stereoselective Synthesis of Acylethenyl Tetrahydropyridino- and Deazepanopyrrolo[1,2-c]imidazolidines via Annulation of Cyclic Imines with Acylethynylpyrroles

Trofimov,

Oparina,

Belyaeva

et al. 2024

Synthesis

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A new and efficient strategy for the stereoselective synthesis of tetrahydropyridino- and deazepano-pyrrolo[1,2-c]imidazolidines has been developed. Annulation of acylethynylpyrroles with six- and seven-membered cyclic imines (MeCN/THF, 20-25 oC, 24-72 h) leads to tetrahydropyrrolo[1’,2’:3,4]imidazo[1,2-a]pyridines and hexahydropyrrolo[1’,2’:3,4]imidazo-[1,2-a]azepines with E-acylethenyl moiety in 29-96% yields.

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Eco-friendly, in-water, and catalyst-free assembly of acylethenylpyrroloimidazoindoles from 3H-indoles and acylpyrrolylacetylenes

Abstract: The merging of fundamentally and biologically important heterocyclic structures such as pyrroles, indoles and imidazoles in molecule of dihydropyrrolo[1',2':3,4]imidazo[1,2-a]indoles functionalized by E-acylethenyl groups has been achieved in water on the...

Cited by 3 publications

References 26 publications

Annulation of 1-methylisoquinoline with pyrrolylacetylenic ketones: catalyst-free stereoselective synthesis of (E)-acylethenylpyrrolo[1’,2’:3,4]imidazo[2,1-a]isoquinolines

Annulation of 1-methylisoquinoline with pyrrolylacetylenic ketones: catalyst-free stereoselective synthesis of (E)-acylethenylpyrrolo[1’,2’:3,4]imidazo[2,1-a]isoquinolines

TEMPO/PhI(OAc)₂ promotes the α-aminophosphinoylation of alcohols with amines and H-phosphine oxides in aqueous medium

Stereoselective Synthesis of Acylethenyl Tetrahydropyridino- and Deazepanopyrrolo[1,2-c]imidazolidines via Annulation of Cyclic Imines with Acylethynylpyrroles

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Eco-friendly, in-water, and catalyst-free assembly of acylethenylpyrroloimidazoindoles from 3H-indoles and acylpyrrolylacetylenes

Abstract: The merging of fundamentally and biologically important heterocyclic structures such as pyrroles, indoles and imidazoles in molecule of dihydropyrrolo[1',2':3,4]imidazo[1,2-a]indoles functionalized by E-acylethenyl groups has been achieved in water on the...

Cited by 3 publications

References 26 publications

Annulation of 1-methylisoquinoline with pyrrolylacetylenic ketones: catalyst-free stereoselective synthesis of (E)-acylethenylpyrrolo[1’,2’:3,4]imidazo[2,1-a]isoquinolines

Annulation of 1-methylisoquinoline with pyrrolylacetylenic ketones: catalyst-free stereoselective synthesis of (E)-acylethenylpyrrolo[1’,2’:3,4]imidazo[2,1-a]isoquinolines

TEMPO/PhI(OAc)2 promotes the α-aminophosphinoylation of alcohols with amines and H-phosphine oxides in aqueous medium

Stereoselective Synthesis of Acylethenyl Tetrahydropyridino- and Deazepanopyrrolo[1,2-c]imidazolidines via Annulation of Cyclic Imines with Acylethynylpyrroles

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Product

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TEMPO/PhI(OAc)₂ promotes the α-aminophosphinoylation of alcohols with amines and H-phosphine oxides in aqueous medium