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Ковтуненко, В. А.; Kucherenko, T. T.; Шишкин, Олег В.; Kisel, V. M.

doi:10.1023/a:1021737714997

Chemistry of Heterocyclic Compounds

2002

DOI: 10.1023/a:1021737714997

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В. А. Ковтуненко

T. T. Kucherenko

Олег В. Шишкин

et al.

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2003

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Cited by 9 publications

(12 citation statements)

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“…We have previously reported 2-(4-oxo-3,4-dihydrothieno[2,3-d]-and - [3,2-d]pyrimidin-2-ylmethyl)-benzoic acids 1 and 2 [2] and 2-(4-oxo-3,4-dihydro-2-quinazolinylmethyl)benzoic acid 3 [3]. This work continues our investigation of thienopyrimidines and quinazolones.…”

supporting

confidence: 69%

Condensed isoquinolines 32. Synthesis of 4H-thieno-[3′,2′:5,6]-and-[2′,3′: 5,6]pyrimido-[1,2-b]isoquinolines and 6,12-dihydro-5H-isoquino-[2,3-a]quinazoline-5,12-dione derivatives

Zadorozhny

Ковтуненко

Туров

et al. 2008

Chem Heterocycl Comp

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dione respectively. NMR spectroscopy showed that an intramolecular acylation of the above acids occurs at the atom N-1 of the pyrimidinone part of the bicycle.We have previously reported 2-(4-oxo-3,4-dihydrothieno[2,3-d]-and -[3,2-d]pyrimidin-2-ylmethyl)-benzoic acids 1 and 2 [2] and 2-(4-oxo-3,4-dihydro-2-quinazolinylmethyl)benzoic acid 3 [3]. This work continues our investigation of thienopyrimidines and quinazolones.The attempted esterification of acids 1-3 by a classical method [4] (heating an alcohol suspension in the presence of concentrated sulfuric acid) gave yellow crystalline materials whose properties differed from the starting materials although not being the esters. Hence like the starting acid they dissolve in a 2N solution of base but, in contrast, are completely insoluble in 2N hydrochloric acid. According to TLC data their chromatographic mobility is markedly greater than the starting acids and esters. The elemental analytical data and chromato-mass spectra of the products obtained point to the loss of a molecule of water from the starting acids, i.e. that an intramolecular acylation had occurred under these reaction conditions. It was found that the sulfuric acid dehydrating agent originally used by us was not a totally suitable reagent since cyclization is accompanied by a vigorous tarring of the reaction product and this significantly lowers the yields. A smoother dehydration occurs upon refluxing a suspension of the acids 1-3 in acetic anhydride.

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supporting

confidence: 69%

Condensed isoquinolines 32. Synthesis of 4H-thieno-[3′,2′:5,6]-and-[2′,3′: 5,6]pyrimido-[1,2-b]isoquinolines and 6,12-dihydro-5H-isoquino-[2,3-a]quinazoline-5,12-dione derivatives

Zadorozhny

Ковтуненко

Туров

et al. 2008

Chem Heterocycl Comp

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“…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.…”

mentioning

confidence: 99%

“…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].…”

mentioning

confidence: 99%

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

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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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“…However, it should be noted that these data may correspond also to a compound with the isomeric structure 8, the formation of which is theoretically possible under conditions when the reactive center for reaction with anthranilic acid is the imino group of salt 4f. From a comparative analysis of the positions of the aromatic protons of the acid 7a, the anthranilic acids 3a,f, and 2-alkylquinazolines [8] corresponding signals were found in strong field at 6.68 (1H, d) and 6.52 (1H, t) for the aromatic protons H-3 and H-5 of the anthranilic acid 3a, which is the evidence of the formation of the structure 7a. It was established in a separate experiment that heating compound 7a in N-methylpyrrolidone-2 in the presence of hydrogen bromide gave isoquinoquinazoline 1f.…”

mentioning

confidence: 95%

Condensed isoquinolines 22. Synthesis and properties of 6,11-dihydro-13H-isoquino-[3,2-b]quinazolin-13-ones

Потиха

2007

Chem Heterocycl Compd

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Keywords: anthranilic acid, o-bromomethylphenylacetonitrile, 6,11-dihydro-13H-isoquino[3,2-b]-quinazol-13-one, rearrangement.Derivatives of the isoquino[3,2-b]quinazoline series are relatively inaccessible and consequently have been little studied. Currently the syntheses of just two derivatives of this heterosystem have been described -6,11-dihydro-13H-isoquino[3,2-b]quinazolin-6-one [2] and 6,11-dihydro-13H-isoquino[3,2-b]quinazolin-13-one (1) [3,4]. Antifungal activity of the latter has been observed [3]. A relatively simple method for the synthesis of derivatives of isoquino[3,2-b]quinazolin-13-one 1 consists of the thermal rearrangement of the isomeric derivatives of 7,12-dihydro-5H-isoquino-[2,3-a]quinazolin-5-one (2) [4,5]. We have previously studied [1] the reaction of o-bromomethylphenylacetonitrile (o-BMPA) with anthranilic acids and their esters, by which a series of Ar-substituted isoquino[2,3-a]quinazolines were obtained. These, in their turn, opened a route to Ar-substituted isoquino [3,2-b]quinazolines, which are difficult to obtain by other methods. In this paper we have studied the characteristics of this reaction, determined by the structure of the substituted anthranilic acids 3a-f.As has been shown earlier [6,7], the reaction of o-BMPA with anthranilic acids and their functional derivatives is a multistep process including the formation of 2-aryl-1,4-dihydro-3(2H)-isoquinolinium bromides 4. In the case of esters of anthranilic acids, isolation of the intermediates was difficult because of their high reactivity which led directly to the cyclic product 2a. In the case of the acids 3a-c, formation of the isoquinolinimines 4a-c was not successfully recorded [1].

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Untitled

Cited by 9 publications

References 5 publications

Condensed isoquinolines 32. Synthesis of 4H-thieno-[3′,2′:5,6]-and-[2′,3′: 5,6]pyrimido-[1,2-b]isoquinolines and 6,12-dihydro-5H-isoquino-[2,3-a]quinazoline-5,12-dione derivatives

Condensed isoquinolines 32. Synthesis of 4H-thieno-[3′,2′:5,6]-and-[2′,3′: 5,6]pyrimido-[1,2-b]isoquinolines and 6,12-dihydro-5H-isoquino-[2,3-a]quinazoline-5,12-dione derivatives

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

Condensed isoquinolines 22. Synthesis and properties of 6,11-dihydro-13H-isoquino-[3,2-b]quinazolin-13-ones

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