Reaction of 6-oxo-, thioxo-2,3-dimethylthieno[2,3-d]pyrimidin-4-ones with electrophelic reagents

Shodiev, M.; Urakov, B. A.; Mukarramov, N. I.; Shakhidoyatov, Kh. M.

doi:10.1007/bf00532040

Cited by 6 publications

(5 citation statements)

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“…However, as can be seen from Table 1, the differences between the calculated charges on the relevant atoms of the common thienopyrimidine moiety of compounds 1-4 (this work) and 21 (see Ref. 1), except for C (2), which is bonded to the H atom in compounds 1 and 2 and to the C atom in tricyclic compounds 2-4, do not exceed 0.01-0.02 e and only for N(3), they reach 0.04 e, and, hence, this cannot serve for interpretation of the differ ences between the behaviors of these compounds.…”

Section: Resultsmentioning

confidence: 67%

Quantum chemical studies of pyrimidin-4-ones

et al. 2015

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Quantum chemical calculations of energies, electronic structures, and molecular geome tries of 3,5,6 trimethylthieno[2,3 d]pyrimidin 4 one (1), tricyclic 2,3 tri , 2,3 tetra , and 2,3 pentamethylene substituted 5,6 dimethylthieno[2,3 d]pyrimidin 4 ones (2-4), carboxy lic acids 5-8 resulting from oxidation of compounds 1-4 at the methyl group in position 5 of thienopyrimidine, methyl esters of these acids (9-12), and products of ipso nitration of esters (13-16) were performed in terms of the HF and DFT (B3LYP) approximations with the 3 21G basis set. Also, calculations for mixed anhydrides of nitric acid and carboxylic acids 17-20 were carried out. The possible causes of differences in the behaviors of 3 unsubstituted and 3 substituted thieno[2,3 d]pyrimidin 4 ones were discussed.Key words: thieno[2,3 d]pyrimidin 4 ones, nitric acid oxidation, ipso substitution, quan tum chemical calculations, Hartree-Fock method (HF), DFT/B3LYP 3 21G method.

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Section: Resultsmentioning

confidence: 67%

Quantum chemical studies of pyrimidin-4-ones

et al. 2015

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“…Yield: 65%, mp 117-119ºС, R f =0.58 (C 6 H 6 /CH 3 OH, 5:1, at RT). On the literary [23] data the ratio of reagents -8:urea (thiourea) was 1:4 (1:1.5). Thus, it was revealed, that increase twice of urea or thiourea amounts promoted essential increase of reaction products 3, 4.…”

Section: -Methyl-3-nitrothieno[23-d]tetrahydroazepino[12-a]pyrimidmentioning

confidence: 97%

“…It allows entering of new functional groups into a molecule, instead of other groups. Reactions are in part investigated on an example of 2-oxo-, -thioxo-5,6dimethylthieno [2,3-d]pyrimidin-4(3H)-ones [23].…”

Section: Introductionmentioning

confidence: 99%

“…It was earlier revealed, that bicyclic thieno [2,3-d]pyrimidin-4(3H)-ones (such as 2-oxo-,thioxo-5,6-dimethylthieno [2,3-d]pyrimidin-4(3H)-ones) at interaction with nitrating mixture (NM) are exposed to electrophilic ipso-substitution of one or two methyl groups with formation 5-or 6-mononitro-and 5,6-dinitro derivatives in good yields [23]. Recently it has been revealed, that tricyclic 2,3-dimethylthieno[2,3-d]pyrimidin-4-ones, containing electron-donating methylene chains (5-7) under action of NM are exposed to oxidation of methyl groups at C-3 up to carboxylic groups instead of the expected ipso-substitution of methyl groups by nitro group [24].…”

Section: Introductionmentioning

confidence: 99%

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Thieno[2,3-d]Pyrimidin-4-Ones. Part 3.* Electrophilic Ipso-Substitution Reactions of Methyl and Methoxycarbonyl Groups

Элмурадов

2013

ACSJ

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Interactions of 5,6-dimethyl-(1), 3,5,6-trimethylthieno[2,3-d]pyrimidin-4(3H)-ones (2) and 2,3-dimethyl-(5-7), 2-methyl-3-methoxycarbonylthieno[2,3-d]dihydropyrrolo-, tetrahydropyrido-, tetrahydroazepino[1,2-a]pyrimidin-4-ones (14-16) with nitrating mixture were investigated. For the first time it is shown, that in dependence on the presence of substituent in position 2 and 3 of pyrimidine and thiophene rings reaction goes in various directions; by electrophilic ipso-substitution of methyl groups at C-5 by nitro group, or its oxidation up to carboxyl groups with formation corresponding 5-carboxy derivatives. It is revealed, that at absence of the substituent in position 3 (compound 1) the electrophilic ipso-substitution of methyl group by nitro group with formation of 5-nitro derivative took

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“…Among heterocyclic compounds the thieno[2,3-d]pyrimidin-4-ones (Melik-Ogandzhanyan et al, 1985;Csukonyi et al, 1986;Shvedov et al, 1975;Shakhidoyatov 1983;Gevald et al, 1966;Kapustina et al, 1992;Peet et al, 1986;Shodiyev et al, 1993) make up a large group of substances that have various physiological activities (Kapustina et al, 1992;Blaskiewich et al, 1975;Wähäla et al, 2005;Lilienkampf et al, 2007;Han et al, 2007;Moore et al, 2006). The structure of the synthesized compound has been investigated by 1 H NMR and XRD analysis.…”

Section: S1 Commentmentioning

confidence: 99%

9-Furfurylidene-2,3-dimethyl-6,7,8,9-tetrahydro-4H-thieno[2′,3′:4,5]pyrimidino[1,2-a]pyridin-4-one

et al. 2010

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The title compound, C17H16N2O2S, was obtained by condensation of 2,3-dimethylthieno[2′,3′:4,5]pyrimidino[1,2-a]pyridin-4-one with furfural in the presence of sodium hydroxide. One of the methylene groups of the tetrahydropyrido ring is disordered over two positions in a 0.87 (1):0.13 (1) ratio. The thieno[2,3-d]pyrimidin-4-one unit and the furan ring are both planar (r.m.s. deviation = 0.535 Å), and coplanar with each other, forming a dihedral angle of 5.4 (1)°. Four weak intermolecular hydrogen bonds (C—H⋯O and C—H⋯N) are observed in the structure, which join molecules into a network parallel to (101).

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Reaction of 6-oxo-, thioxo-2,3-dimethylthieno[2,3-d]pyrimidin-4-ones with electrophelic reagents

Cited by 6 publications

References 1 publication

Quantum chemical studies of pyrimidin-4-ones

Quantum chemical studies of pyrimidin-4-ones

Thieno[2,3-d]Pyrimidin-4-Ones. Part 3.* Electrophilic Ipso-Substitution Reactions of Methyl and Methoxycarbonyl Groups

9-Furfurylidene-2,3-dimethyl-6,7,8,9-tetrahydro-4H-thieno[2′,3′:4,5]pyrimidino[1,2-a]pyridin-4-one

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