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Теренин, В. И.; Sumtsova, E. A.; Вацадзе, С. З.; Kabanova, E. V.; Leshcheva, I. F.; Плешкова, А. П.; Зык, Н. В.

doi:10.1023/a:1026158724018

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“…[207,208] and dipyrrolo[1,2-a;2',1'-c]pyrazines [209][210][211][212][213][214][215][216] in electrophilic substitution reactions (protonation, acylation, aminomethylation, nitration, formylation, phosphorylation) was investigated systematically. [207,208] and dipyrrolo[1,2-a;2',1'-c]pyrazines [209][210][211][212][213][214][215][216] in electrophilic substitution reactions (protonation, acylation, aminomethylation, nitration, formylation, phosphorylation) was investigated systematically.…”

Section: Rshmentioning

confidence: 99%

Chemistry of heterocyclic compounds at the Department of Organic Chemistry, Chemical Faculty, M. V. Lomonosov State University. (Review)

Yurovskaya

2005

Chem Heterocycl Compd

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Section: Rshmentioning

confidence: 99%

Chemistry of heterocyclic compounds at the Department of Organic Chemistry, Chemical Faculty, M. V. Lomonosov State University. (Review)

Yurovskaya

2005

Chem Heterocycl Compd

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“…Nitration was carried out by treatment with a mixture of nitric acid (d = 1.42 g/ml) and acetic anhydride at -10°C. The nitronium ion attacks the free α-position of the pyrrole ring to form the mononitro and dinitro derivatives [3].We have studied nitration reactions of pyrrolo[1,2-a]pyrazines containing alkyl and aralkyl substituents at the 1 and 6 positions of the heterocycle when treated with a nitrating mixture, with acetyl nitrate, and with nitric acid. N N R N N R O 2 N N N R NO 2 N N R NO 2 O 2 N HNO 3 conc.…”

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Nitration of Pyrrolo[1,2-a]pyrazines

Теренин

Butkevich

Плешкова

2005

Chem Heterocycl Compd

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Pyrrolodiazine derivatives have attracted the attention of researchers because they have a broad spectrum of physiological activity. Azole and azine moieties are encountered in many natural biologically active compounds such as alkaloids and biogenic amines. The bicyclic aromatic system of pyrrolo[1,2-a]pyrazine has been poorly studied due to the relative difficulty of obtaining it, its low reactivity relative to electrophiles, and also the ambiguous reaction pathways of these compounds [1]. The relative stability of the pyrrolo[1,2-a]pyrazine system with respect to treatment with weak electrophilic reagents is suggested by the fact that the unsubstituted pyrrolo[1,2-a]pyrazine, when boiled with excess acetic anhydride for 24 h, forms 6-acetylpyrrolo[1,2-a]pyrazine in only 16% yield [2].Earlier we studied the nitration reaction for asymmetrically substituted dipyrrolo[1,2-a;2',1'-c]pyrazine systems. Nitration was carried out by treatment with a mixture of nitric acid (d = 1.42 g/ml) and acetic anhydride at -10°C. The nitronium ion attacks the free α-position of the pyrrole ring to form the mononitro and dinitro derivatives [3].We have studied nitration reactions of pyrrolo[1,2-a]pyrazines containing alkyl and aralkyl substituents at the 1 and 6 positions of the heterocycle when treated with a nitrating mixture, with acetyl nitrate, and with nitric acid. N N R N N R O 2 N N N R NO 2 N N R NO 2 O 2 N HNO 3 conc. H 2 SO 4 1a-d 2a-d 3a-d 4a-d + + + 1-4 a R = Me; b R = Et; c R = Pr; d R = i-Pr __________________________________________________________________________________________ 1 M.

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Dipyrrolo[1,2‐a;2′,1′‐c]pyrazines. Part 6. Electrophilic Substitution in a Series of Dipyrrolo[1,2‐a;2′,1′‐c]pyrazine and 5,6‐Dihydrodipyrrolo[1,2‐a;2′,1′‐c]pyrazine Derivatives. Phosphorylation of Dipyrrolo[1,2‐a;2′,1′‐c]pyrazines.

et al. 2004

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2',1'-c]pyrazine and 5,6-Dihydrodipyrrolo[1,2-a;2',1'-c]pyrazine Derivatives. Phosphorylation of Dipyrrolo[1,2-a;2',1'-c]pyrazines. -The phosphorylation of the title dipyrrolopyrazine derivatives (I) with PCl3 occurs regioselectively and gives rise only to the monosubstituted products (IV). Similar phosphorylation using PBr 3 instead of PCl 3 leads to complex mixtures of both monosubstitution and disubstitution products. -(TERENIN, V. I.; SUMTSOVA, E. A.; VATSADZE, S. Z.; KABANOVA, E. V.; LESHCHEVA, I. F.; PLESHKOVA, A. P.; ZYK, N. V.; Chem. Heterocycl. Compd. (N. Y.) 39 (2003) 7, 943-952; Lomonosov Moscow State Univ., Moscow 119899, Russia; Eng.) -Staver 18-161

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Cited by 4 publications

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Chemistry of heterocyclic compounds at the Department of Organic Chemistry, Chemical Faculty, M. V. Lomonosov State University. (Review)

Chemistry of heterocyclic compounds at the Department of Organic Chemistry, Chemical Faculty, M. V. Lomonosov State University. (Review)

Nitration of Pyrrolo[1,2-a]pyrazines

Dipyrrolo[1,2‐a;2′,1′‐c]pyrazines. Part 6. Electrophilic Substitution in a Series of Dipyrrolo[1,2‐a;2′,1′‐c]pyrazine and 5,6‐Dihydrodipyrrolo[1,2‐a;2′,1′‐c]pyrazine Derivatives. Phosphorylation of Dipyrrolo[1,2‐a;2′,1′‐c]pyrazines.

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