Fused isoquinolines: 3-aryl-2,3,4,5-tetrahydro-1H-pyrrolo[2,3-c]isoquinoline-1,5-dione-2-spiro-4′-(1′-alkyl-1′,4′-dihydropyridine)s

Kucherenko, T. T.; Gutsul, R. M.; Kisel, V. M.; Ковтуненко, В. А.

doi:10.1016/j.tet.2003.10.009

Cited by 10 publications

(13 citation statements)

References 10 publications

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“…2-(Cyanomethyl)benzoic acid (1) on condensation with benzylamine [2], aniline [3], and substituted anilines [4] behaves as 1,5-dielectrophilic synthon and gives derivatives of 3-aminoisocarbostyrene. On interaction with anthranilic acid or its esters acid 1 behaves as a monofunctional compound to give derivatives of 2-[(3,4-dihydro-4-oxo-2-quinazolinyl)methyl]benzoic acid [5].…”

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confidence: 99%

Condensed isoquinolines 27*. Synthesis and oxidation reactions of 5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-one

Потиха

Gutsul

Туров

et al. 2008

Chem Heterocycl Comp

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Keywords: 2-aminobenzylamine, [6,6′]bi[isoquino[3,2-b]quinazoline], dibenzo[b,f][1,8]naphthyridine, isoquino[3,2-b]quinazoline, 2-(cyanomethyl)benzoic acid, oxidation, rearrangement.2-(Cyanomethyl)benzoic acid (1) on condensation with benzylamine [2], aniline [3], and substituted anilines [4] behaves as 1,5-dielectrophilic synthon and gives derivatives of 3-aminoisocarbostyrene. On interaction with anthranilic acid or its esters acid 1 behaves as a monofunctional compound to give derivatives of 2-[(3,4-dihydro-4-oxo-2-quinazolinyl)methyl]benzoic acid [5].In the present work we have investigated the condensation of acid 1 with 2-aminobenzylamine (2). This reaction was studied previously [6, 7], but the structure of the condensation product -5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-one (3) was not shown conclusively.We have found that compound 3 can be obtained in higher yield (82%) by boiling the reagents in butanol for 5 h than by carrying out the reaction in anyl (6 h, 68% yield [6, 7]. Prolongation the reaction is considerably decreased by using DMF (2 h) as the solvent and the reaction product does not require further purification. However, as a result of unexpected oxidation, the yield of compound 3 in the last case was considerably reduced (<50%).The reaction of 2-(cyanomethyl)benzoic acid with 2-aminobenzylamine may lead to condensation products with either an angular structure -5,6-dihydro-12H-isoquino[2,3-a]quinazolin-12-one (4) or a linear structure -5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-one (3). It is not possible using IR and 1 H NMR spectra to determine unequivocally the structures of 3 and 4, it can only be said that an enamine structure is present: ν NH 3250 cm -1 , δ NH 9.72 (s) and δ =CH 5.85 ppm (s). In addition the absence of coupling between the protons of the amino and methylene groups (5.06 ppm, 2H, s) indicates the formation of compound 3. _______ * For Communication 26 see [1].

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confidence: 99%

Condensed isoquinolines 27*. Synthesis and oxidation reactions of 5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-one

Потиха

Gutsul

Туров

et al. 2008

Chem Heterocycl Comp

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“…На образование спиросочленен-ной системы указывают, в частности, характерный сигнал спиро-углерода 5-C в области 70-80 м.д. и типичная для 1,4-дигидропиридинов [13] карти-на поглощения в спектре ЯМР Для соединения 2h, которое является предста-вителем ряда 8-алкил-1,2,8-триазаспиро [4.5]дека-2,6,9-триенов, был проведен РСА, который одно-значно подтвердил ортогональность спиросочле-ненных плоскостей (рис. ).…”

Section: таблицаunclassified

“…Внут-римолекулярный вариант этой реакции, сопро-вождаемый спироциклизацией, использовался при синтезе алкалоида науклефина [9,10] и сложных гетероциклических систем [11,12]. Возможность образования новой С-N связи в рамках этого под-хода, сопровождаемая гетероциклизацией, была впервые показана в наших работах [13,14].…”

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The synthetic method for 1-(phenyl)alkyl-3-acyl-1,2,8-triazaspiro[4.5]decanes

Kovtunenko¹,

Потиха²,

Bulda³

et al. 2016

J. org. pharm. chem.

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confidence: 99%

“…the starting 3-aminoisocarbostyryls in different chemical shift ranges and differ in their multiplicity (for 1d,e) [1, 2,9]: 10.5-10.7 (s, H-2), 5.4-5.9 (s, H-4), 7.6-7.9 (s, 3-NH, 1a-c) and 5.4-5.9 ppm (t, 3-NH, 1d,e). The signal for 3-NH proton is lacking in the spectra of the alkylation products, indicating the formation of compounds with structure 2.…”

mentioning

confidence: 99%

Alkylation of 3-aminoisocarbostyryl derivatives

Потиха

Gutsul²,

Ковтуненко

et al. 2011

Chem Heterocycl Comp

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In this work, we continued our study of the chemical properties of uncondensed derivatives of 3-aminoisoquinolin-1(2H)-one (3-aminoisocarbostyryl) [1,2] and examined the reaction of alkyl halides with isocarbostyryls substituted at the 3-amino group. The alkylation of 3-aminoisocarbostyryls has been studied previously predominantly for condensed systems (reactions with alkyl halides [3-6] and dimethyl sulfate [7]). Only the 1,4-conjugate addition of olefins to 3-aminoisoquinolin-1(2H)-one has been described for uncondensed derivatives [8].Electrophilic substitution in 3-aminocarbostyryls, which are ambident nucleophiles, leads to different products depending both on the structure of the reagents and reaction conditions [3][4][5][6][7]. Thus, heating solutions of 3-(arylamino)isoquinolin-1(2H)-ones 1a-c and 3-(alkylamino)isoquinolin-1(2H)-ones 1d and 1e in acetonitrile with phenacyl bromide or alkyl halides (MeI, EtI, benzyl chloride) leads to a complex mixture of reaction products, which failed to be separated. The same result was obtained in an attempt to carry out the reaction by fusion of a mixture of reagents (with phenacyl bromide and benzyl chloride) or heating of the mixture in the presence of i-OPrNa in 2-propanol (according to mass-spectrometric and 1 H NMR spectral data).We have found that compounds 1a,b,d,e react with alkyl halides (MeI, EtI, and benzyl chloride) in DMF solution at room temperature in the presence of NaH and are converted into 3-(alkylanilino)isoquinolin-1(2H)-ones 2a and 2b and 3-(dialkylamino)isoquinolin-1(2H)-ones 2c-e.Isoquinolinones 2a-e were isolated from the reaction product mixtures as pure compounds and their structures were established using 1 H NMR spectroscopy (Tables 1-3).

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Fused isoquinolines: 3-aryl-2,3,4,5-tetrahydro-1H-pyrrolo[2,3-c]isoquinoline-1,5-dione-2-spiro-4′-(1′-alkyl-1′,4′-dihydropyridine)s

Cited by 10 publications

References 10 publications

Condensed isoquinolines 27*. Synthesis and oxidation reactions of 5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-one

Condensed isoquinolines 27*. Synthesis and oxidation reactions of 5,13-dihydro-11H-isoquino[3,2-b]quinazolin-11-one

The synthetic method for 1-(phenyl)alkyl-3-acyl-1,2,8-triazaspiro[4.5]decanes

Alkylation of 3-aminoisocarbostyryl derivatives

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