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Borovik, V. P.; Shkurko, O. P.

doi:10.1023/a:1021688616234

Cited by 7 publications

(10 citation statements)

References 3 publications

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“…The compound is hygroscopic. 13 C NMR, δ: 108.41 (C(4а)); 111.89 (C(8)); 118.52 (C(4b)); 120.91 (C(6)); 121.55 (C(5)); 127.39 (C(7)); 128.56 (C m , C o ); 130.20 (C p ); 137.34 (C i ); 138.37 (C(8а)); 157.17 (C(9a)); 159.28 (C(4)); 163.56 (C(2)).…”

Section: Bis(4 Phenyl 9h Pyrimido[45 B]indol 2 Yl) Disulfide (4)mentioning

confidence: 99%

“…The 1 H and 13 C NMR data were reported previously. 13 9 Methyl 4 phenylpyrimido[4,5 b]indole (10). Pyrimido indole 6 (0.10 g, 0.4 mmol) was added to a solution of sodium ethoxide prepared from sodium (0.019 g, 0.8 mmol) and an hydrous ethanol (10 mL), the mixture was stirred for 10 min and concentrated to dryness in vacuo at 35 °C.…”

Section: Phenyl 9h Pyrimido[45 B]indole (6)mentioning

confidence: 99%

“…2)). 13 C NMR, δ: 27.60 (Me); 110.08 (C(4а)); 110.33 (C(8)); 118.11 (C(4b)); 120.98 (C(6)); 121.83 (C(5)); 127.67 (C(7)); 128.57 (C m ); 128.65 (C o ); 129.92 (C p ); 138.03 (C i ); 139.66 (C(8а)); 154.00 (C(2)); 155.36 (C(9a)); 158.74 (C(4)).…”

Section: Phenyl 9h Pyrimido[45 B]indole (6)mentioning

confidence: 99%

“…The reductive desulfurization of disulfide 4 with Raney nickel led to 4 phenyl 9H pyrimido [4,5 b]in dole (6) in a good yield. Previously, 13 we isolated this compound as a minor product upon the reaction of 2 chloropyrimidoindole 5 with hydrazine hydrate and upon hydrogenation of the corresponding 2 nitramino derivative.…”

mentioning

confidence: 99%

“…This reaction proceeds with difficulty, its completion re quiring heating in DMSO for many hours. The retarda tion of nucleophilic substitution in the pyrimidoindole series (in relation to chloro and nitramino derivatives) 13 with respect to the pyrimidine analogs attests to substan tial deactivating effect of the electron releasing pyrrole fragment on the reactivity of the pyrimidoindole mol ecule. This conclusion is also confirmed by data on the mobility of the MeSO 2 group (see below).…”

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confidence: 99%

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Synthesis of 2-thio derivatives of 4-phenyl-9H-pyrimido[4,5-b]indole

2006

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The reaction of 3 benzylidene 2 ethoxyindolenine tetrafluoroborate with thiourea gives a mixture of 4 phenylpyrimido [4,5 b]indole 2(1H ) thione, its 3,4 dihydro derivative, and the corresponding disulfide, the product ratio depending on the reaction conditions. A number of transformations of the resulting compounds, in particular, those giving 2 alkylthio pyrimido indole derivatives are described. Key words: 4 phenyl 9H pyrimido[4,5 b]indole 2(1H ) thione, 2 alkylthio derivatives of 4 phenyl 9H pyrimido[4,5 b]indole, alkylation, oxidation, nucleophilic substitution, desulfu rization.The functional derivatives of pyrimido[4,5 b]indole, in particular, synthetically most available 2 and 4 amino substituted derivatives, possess a broad spectrum of bio logical activities and present interest as a base for the development of new medicines. 1-3 The corresponding thio derivatives may also attract attention as biologically active substances, since compounds possessing antioxi dant, antihypoxic, and hepatoprotector activities have been found in the series of related heterocyclic systems, 1,2,4 triazino[5,6 b] and [6,5 b]indoles. 4-6 In order to extend the range of functional derivatives of 4 phenyl pyrimido[4,5 b]indole and to study their properties, we attempted to synthesize its 2 thio derivatives.Previously, we carried out the reaction of 3 ben zylidene 2 ethoxyindolenine tetrafluoroborate (1) with thiourea, which yielded a product identified as 4 phenyl pyrimido[4,5 b]indole 2,4(1H ) thione (2) 7 (Scheme 1). A repeated detailed study of the reaction showed that this product is actually a mixture of thione 2, its 3,4 dihydro derivative 3, and disulfide 4. Similar analytical and spec troscopic characteristics of compounds 2-4, their poor solubility in most organic solvents, similar chromato graphic behaviors of thiones 2 and 3, and easy transfor mation into disulfide 4 make separation and identifica tion of these compounds a difficult task. The presence of both thiones in the mixture can be detected by mass spec trometry, whereas disulfide 4 is not detected due to its very low volatility. All three components of the mixture can be observed by HPLC with mass selective detection (HPLC MSD). In addition, the presence of disulfide 4 can be determined by TLC.

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Section: Bis(4 Phenyl 9h Pyrimido[45 B]indol 2 Yl) Disulfide (4)mentioning

confidence: 99%

Section: Phenyl 9h Pyrimido[45 B]indole (6)mentioning

confidence: 99%

Section: Phenyl 9h Pyrimido[45 B]indole (6)mentioning

confidence: 99%

mentioning

confidence: 99%

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confidence: 99%

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Synthesis of 2-thio derivatives of 4-phenyl-9H-pyrimido[4,5-b]indole

2006

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Fe₃O₄‐SAHPG‐Pd⁰ nanoparticles: A ligand‐free and low Pd loading quasiheterogeneous catalyst active for mild Suzuki–Miyaura coupling and CH activation of pyrimidine cores

Azizollahi

Garcı́a-López

2020

Applied Organom Chemis

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This paper reports a green magnetic quasiheterogeneous efficient palladium catalyst in which Pd 0 nanoparticles have been immobilized in self-assembled hyperbranched polyglycidole (SAHPG)-coated magnetic Fe 3 O 4 nanoparticles (Fe 3 O 4-SAHPG-Pd 0). This catalyst has been used for effective ligandless Pd catalyzed Suzuki-Miyaura coupling reactions of different aryl halides with substituted boronic acids at room temperature and in aqueous media. Herein, SAHPG is used as support; it also acts as a reducing agent and stabilizer to promote the transformation of Pd II to Pd 0 nanoparticles. Also, this environmental friendly quasiheterogeneous catalyst is employed for the first time in the synthesis of new pyrimido[4,5-b]indoles via oxidative addition/C H activation reactions on the pyrimidine rings, which were obtained with higher yield and faster than when Pd(OAc) 2 was used as the catalyst. Interestingly, the abovementioned catalyst could be recovered in a facile manner from the reaction mixture by applying an external magnet device and recycled several times with no significant decrease in the catalytic activity.

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Synthesis of Functional 2‐Substituted 4‐Phenyl‐9H‐pyrimido[4,5‐b]indoles.

Borovik

Shkurko

2003

ChemInform

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Fused pyrimidine derivativesFused pyrimidine derivatives R 0515 Synthesis of Functional 2-Substituted 4-Phenyl-9H-pyrimido[4,5-b]indoles. -In contrast to a previously developed procedure for the synthesis of pyrimidoindoles, a better yield of 2-oxo derivative (II) is obtained by diazotization of aminopyrimidoindole (I) without additional purification. 2-Oxo derivative (II) and 2-chloro derivative (III) serve as key compounds for the preparation of a number of functional derivatives. Likewise of interest for the synthesis of 2-substituted pyrimidoindoles is the preparation of 2-nitramino derivative (XII) according to a procedure analogous to that described previously. An attempted preparation of 2-hydrazinopyrimidoindole from (XII) fails, only hydrogenolysis and elimination of the hydrazine group occur. -(BOROVIK, V. P.; SHKURKO*, O. P.; Russ.

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Cited by 7 publications

References 3 publications

Synthesis of 2-thio derivatives of 4-phenyl-9H-pyrimido[4,5-b]indole

Synthesis of 2-thio derivatives of 4-phenyl-9H-pyrimido[4,5-b]indole

Fe₃O₄‐SAHPG‐Pd⁰ nanoparticles: A ligand‐free and low Pd loading quasiheterogeneous catalyst active for mild Suzuki–Miyaura coupling and CH activation of pyrimidine cores

Synthesis of Functional 2‐Substituted 4‐Phenyl‐9H‐pyrimido[4,5‐b]indoles.

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Untitled

Cited by 7 publications

References 3 publications

Synthesis of 2-thio derivatives of 4-phenyl-9H-pyrimido[4,5-b]indole

Synthesis of 2-thio derivatives of 4-phenyl-9H-pyrimido[4,5-b]indole

Fe3O4‐SAHPG‐Pd0 nanoparticles: A ligand‐free and low Pd loading quasiheterogeneous catalyst active for mild Suzuki–Miyaura coupling and CH activation of pyrimidine cores

Synthesis of Functional 2‐Substituted 4‐Phenyl‐9H‐pyrimido[4,5‐b]indoles.

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Fe₃O₄‐SAHPG‐Pd⁰ nanoparticles: A ligand‐free and low Pd loading quasiheterogeneous catalyst active for mild Suzuki–Miyaura coupling and CH activation of pyrimidine cores