Chemistry of 3-acyl-2-haloindoles (Review)

Денькина, С. В.; Суздалев, К. Ф.

doi:10.1007/s10593-013-1181-9

Cited by 5 publications

(1 citation statement)

References 72 publications

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“…10 2-Haloindole-3-carbaldehydes are available and versatile reagents for the synthesis of numerous indole derivatives. 11 Inspired by our previous works concerning the synthesis of pyrimido [1,2-a]indole 12 and oxazolo[3,2-a]-indole 13 systems, we aimed to obtain imidazo [1,2-a]indoles using 2-chloroindole-3-carbaldehyde 11 as the starting compound. First we introduced a two-carbon fragment at the indole nitrogen atom by alkylation of indole-3-carbaldehyde 11 with 2-bromo-1,1-diethoxyethane and obtained the diethyl acetal 12 (Scheme 1).…”

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Synthesis of Imidazo[1,2-a]Indoles from 2-Chloroindole-3-Carbaldehyde

Суздалев

Vikrischuk

Prikhodko

et al. 2016

Chem Heterocycl Comp

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A two-step approach towards the synthesis of imidazo[1,2-a]indoles from 2-chloroindole-3-carbaldehyde has been developed. It comprises the N-alkylation of indole ring by 2-bromo-1,1-diethoxyethane followed by a treatment with aromatic amine hydrochlorides. The reaction proceeds as a nucleophilic substitution of the chlorine atom at position 2 of the indole ring followed by cyclization along with the condensation at the aldehyde group. Imidazo[1,2-a]indoles were isolated as protonated Schiff bases. Their structure was proved by 1 H and 13 C NMR spectroscopy and X-ray structural analysis.

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confidence: 99%

Synthesis of Imidazo[1,2-a]Indoles from 2-Chloroindole-3-Carbaldehyde

Суздалев

Vikrischuk

Prikhodko

et al. 2016

Chem Heterocycl Comp

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ChemInform Abstract: Chemistry of 3‐Acyl‐2‐haloindoles

Денькина¹,

Суздалев²

2013

ChemInform

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A simple and facile synthesis of tricyclic-fused pyrimido[4,5-b]indol-2-amines

Gao

Wang

2017

Mol Divers

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In the present investigation, a simple and facile synthetic strategy for the construction of a series of structurally interesting tricyclic-fused N-alkyl-9H-pyrimido[4,5-b]indol-2-amines has been successfully achieved. Our synthesis, based on the annulation reaction between readily available 2-chloroindole-3-carbaldehydes or 3-acetyl-2-chloroindoles and guanidine nitrate using KOH as the base in refluxing EtOH medium, has the attractive features such as mild and economical reaction conditions and easy handing with lesser impact on the environment.

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Chemistry of 3-acyl-2-haloindoles (Review)

Cited by 5 publications

References 72 publications

Synthesis of Imidazo[1,2-a]Indoles from 2-Chloroindole-3-Carbaldehyde

Synthesis of Imidazo[1,2-a]Indoles from 2-Chloroindole-3-Carbaldehyde

ChemInform Abstract: Chemistry of 3‐Acyl‐2‐haloindoles

A simple and facile synthesis of tricyclic-fused pyrimido[4,5-b]indol-2-amines

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