The Nenitzescu reaction (review)

Граник, В. Г.; Lyubchanskaya, V. M.; Mukhanova, T. I.

doi:10.1007/bf00780660

Cited by 18 publications

(10 citation statements)

References 44 publications

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“…1- 4 We studied the reactions of p quinones with drotaverine, which is a well known spasmolytic agent widely used in medicine as hydrochloride. 1- 4 We studied the reactions of p quinones with drotaverine, which is a well known spasmolytic agent widely used in medicine as hydrochloride.…”

mentioning

confidence: 99%

Annelation of drotaverine by p-quinones to form hydroxyindolo- and hydroxybenzindoloisoquinoline derivatives

2005

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1 (3,4 Diethoxybenzyl) 6,7 diethoxy 3,4 dihydroisoquinoline (drotaverine, 1a) reacts with p benzoquinone (2) and p naphthoquinone (3) in nitromethane or during fusion to give 5 (3,4 diethoxyphenyl) 7,8 diethoxy 3 hydroxy 5a,10,11,12 tetrahydroindolo[2,1 a]iso quinoline (4) and 7 (3,4 diethoxyphenyl) 9,10 diethoxy 5 hydroxy 7a,12,13,14 tetra hydrobenz[g]indolo[2,1 a]isoquinoline (5), respectively. Compounds 4 and 5 are smoothly alkylated at the oxygen atom in the presence of bases. The structure of one alkylation product, viz., 3 allyloxy 5 (3,4 diethoxyphenyl) 7,8 diethoxy 5a,10,11,12 tetrahydroindolo[2,1 a]iso quinoline, was established by X ray diffraction analysis.

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confidence: 99%

Annelation of drotaverine by p-quinones to form hydroxyindolo- and hydroxybenzindoloisoquinoline derivatives

2005

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“…For our Nenitzescu reaction [10][11][12][13][14], pyridine-2,4,6-triamine (5) was dissolved in ethanol and 2 eq. of 1,4-benzoquinone (4) added carefully [15].…”

Section: Methodsmentioning

confidence: 99%

Unexpected formation of pyridodiindole derivatives with cytotoxic activity via double nenitzescu reaction

Willemann

Waibel

Troschütz

et al. 2008

Journal of Heterocyclic Chem

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“…На основе анализа литературных данных [7,[17][18][19] Направление 1 включает протонирование атома азота и замыкание цикла с образованием интермедиата (В), которое образуется за счет атаки неподеленной пары электронов кислорода карбонильной группы по электронодефицитному α-положению енамина. В результате последующего отщепления ариламина образуется конечный продукт -производное бензофурана (III).…”

Section: схемаunclassified

Synthesis of Benzofuran Derivatives on the Basis of N-Acyl-1,4-Benzoquinone Monoimines

Konovalova

Avdeenko

Lysenko

et al. 2017

Odesa National University Herald. Chemistry

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В результате реакции Неницеску N-ароил-, N-бензилиденацетил-и N-ариламинокарбонил-1,4-бензохинонмоноиминов с 4-(4-толуидино)пент-3-ен-2-оном в одну стадию при комнатной температуре в уксусной кислоте получены 3-ацетил-5ациламидо-2-метилбензофураны. Наличие протонов в реакционной среде значительно облегчает протонирование интермедиатов, образующихся в ходе реакции. Производные индола в апротонных растворителях получить не удалось. Ключевые слова: 3-ацетил-5-ациламидо-2-метилбензофуран, 4-(4-толуидино)пент-3ен-2-он, реакция Неницеску, N-ацил-1,4-бензохинонмоноимины.

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The Nenitzescu reaction (review)

Cited by 18 publications

References 44 publications

Annelation of drotaverine by p-quinones to form hydroxyindolo- and hydroxybenzindoloisoquinoline derivatives

Annelation of drotaverine by p-quinones to form hydroxyindolo- and hydroxybenzindoloisoquinoline derivatives

Unexpected formation of pyridodiindole derivatives with cytotoxic activity via double nenitzescu reaction

Synthesis of Benzofuran Derivatives on the Basis of N-Acyl-1,4-Benzoquinone Monoimines

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