Synthesis of 4-nitro-γ-carbolines by Graebe–Ullmann reaction

Shuvalov, Vladislav Yu.; Shestakov, Alexander N.; Kulakova, Lyudmila A.; Куратова, Анна К.; Воронцова, М. А.; Сагитуллина, Г. П.

doi:10.1007/s10593-019-02547-w

Cited by 3 publications

(2 citation statements)

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“…The classical Graebe-Ullmann synthesis [11] of γ-carbolines, one of the very early protocols in the domain, is based on the thermal decomposition of N-pyridylbenzotriazoles. Later, the reaction conditions were modified to make this reaction more versatile and operationally simple such as by the use of microwave irradiation [12].…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 1-indolyl-3,5,8-substituted γ-carbolines: one-pot solvent-free protocol and biological evaluation

Dudhe

Krishnan

Yadav

et al. 2021

Beilstein J. Org. Chem.

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1,5-Disubstituted indole-2-carboxaldehyde derivatives 1a–h and glycine alkyl esters 2a–c are shown to undergo a novel cascade imination-heterocylization in the presence of the organic base DIPEA to provide 1-indolyl-3,5,8-substituted γ-carbolines 3aa–ea in good yields. The γ-carbolines are fluorescent and exhibit anticancer activities against cervical, lung, breast, skin, and kidney cancer cells.

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Section: Introductionmentioning

confidence: 99%

Synthesis of 1-indolyl-3,5,8-substituted γ-carbolines: one-pot solvent-free protocol and biological evaluation

Dudhe

Krishnan

Yadav

et al. 2021

Beilstein J. Org. Chem.

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“…Monitoring of reactions and purity of the compounds obtained was by TLC on Silufol UV-254 plates, visualization under UV light. All chemicals were of analytical grade and purchased from Sigma-Aldrich Chemical Co. 2-Nitro-1-phenylethan-1-ones, 21` b c d substituted chalcones 15 , 22a–d and β-nitroenones 23a,b were synthesized according to the described procedures.…”

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confidence: 99%

Efficient Synthesis of Pyrido[3,4-c]cinnolines and Pyrido[3,2-c]cinnolines by Intramolecular Azo Coupling Reaction of 4,6-Diaryl-3-pyridine Diazonium Salts and Study of Their Antiviral Activity

Sagitullina,

Fisenko,

Shuvalov

et al. 2023

Synthesis

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A new method was proposed for the synthesis of pyrido[3,4-c]cinnolines and pyrido[3,2-c]cinnolines. Pyridine-3-diazonium tetrafluoroborates, containing donor methoxy groups in one of the aryl substituents, form pyridocinnolines at 0°C by intramolecular azo coupling reaction. The 2´-methoxy group in the aryl substituent of the pyridine-3-diazonium salt participates in the aromatic nucleophilic substitution reaction, which results in the elimination of the diazo group to form benzofuro[2,3-c]pyridine and benzofuro[3,2-b]pyridine. The intermediate and target reaction products were isolated in high yields.

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Carboline Regioisomers Based on Unified Synthetic Approaches

Arshad

Mordi

2023

Adv Synth Catal

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Carbolines are a prominent class of tricyclic alkaloids omnipresent in natural products and bioactive compounds. Four different carboline regioisomers are known (α-, β-, γ-, and δ-carbolines), which can be classified according to the nitrogen atom position inside the pyridine ring. As an emerging structural motif in drug discovery, a multitude of synthetic methods have been established for the construction of carboline frameworks, which in general requires customized approaches for the assembly of each regioisomer. Distinguishingly, their frameworks are also accessible from unified approaches, which are capable of generating multiple regioisomers, thus suitable for introducing diversity in isomeric carbolines. In this review, the construction of isomeric carbolines based on unified synthetic approaches is summarized.

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Synthesis of 4-nitro-γ-carbolines by Graebe–Ullmann reaction

Cited by 3 publications

References 2 publications

Synthesis of 1-indolyl-3,5,8-substituted γ-carbolines: one-pot solvent-free protocol and biological evaluation

Synthesis of 1-indolyl-3,5,8-substituted γ-carbolines: one-pot solvent-free protocol and biological evaluation

Efficient Synthesis of Pyrido[3,4-c]cinnolines and Pyrido[3,2-c]cinnolines by Intramolecular Azo Coupling Reaction of 4,6-Diaryl-3-pyridine Diazonium Salts and Study of Their Antiviral Activity

Carboline Regioisomers Based on Unified Synthetic Approaches

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