1,3,7-Triazapyrene: the first case of hetarylation of benzene and its analogs

Демидов, О. П.; Боровлев, И. В.; Saigakova, N. A.

doi:10.1007/s10593-013-1331-0

Cited by 7 publications

(4 citation statements)

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“…1 (27), 383 (M + , 100), 382 (59), 369 (13), 368 (46), 367 (17), 366 (11), 364 (12), 352 (10), 91 (18) ): ṽ = 762 (s), 787 (vs), 888 (m), 1016 (s), 1090 (s), 1259 (m), 1397 (w), 1445 (w), 1484 (w), 1556 (w), 1599 (w), 2918 (w), 2961 (w), 3025 (w). MS (EI, 70 eV): m/z = 398 (29), 397 (M + , 100), 396 (43), 383 (15), 382 (50), 381 (14), 380 (12), 365 (12), 364 (12), 182 (16), 91 (17). HRMS (EI) m/z: [M + ] calcd for C 30 H 23 N 397.1825, found 397.1814.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…This compound has been prepared by thermal cyclization, by using a lengthy nine step-sequence, by PPA (polyphosphoric acid)-induced Beckmann rearrangement, and by peri -annulation with sym -triazines . In the course of the development of Pd-catalyzed cross-coupling reactions, ,− a number of di- and triazapyrenes and related molecules have been published. ,− Recently, the group of Kozaki published an intramolecular Cu(I)-catalyzed C–H functionalization approach, while Han et al applied the classical Bischler–Napieralski cyclization of amide precursors …”

Section: Introductionmentioning

confidence: 99%

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Synthesis of 2-Azapyrenes and Their Photophysical and Electrochemical Properties

et al. 2020

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A series of 5,7,9-substituted 2-azapyrenes were synthesized for the first time. The synthesis relies on Brønsted acid promoted benzannulation of alkyne precursors prepared by palladium-catalyzed cross-coupling reactions. The synthetic strategy is efficient and the scope covers a variety of functional groups. The electrochemical behavior and photophysical properties of the products were investigated by UV−vis and fluorescence spectroscopy, cyclic voltammetry, and DFT calculations.

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Section: ■ Experimental Sectionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis of 2-Azapyrenes and Their Photophysical and Electrochemical Properties

et al. 2020

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“…A mixture of the corresponding 1,3,7‐triazapyrene , 2‐methyl‐1,3,7‐triazapyrene , 6‐(4′‐tolyl)‐1,3,7‐triazapyrene , or 6‐(4′‐methoxyphenyl)‐1,3,7‐triazapyrene (0.5 mmol), water (5 mL), KOH (9 mmol), K 3 Fe(CN) 6 (3 mmol), and the appropriate alcohol (5 mL) was stirred vigorously at room temperature during the time indicated in the succeeding text for each compound. In the middle of the process, the extra portion of K 3 Fe(CN) 6 (3 mmol) was added.…”

Section: Methodsmentioning

confidence: 99%

Ureas as a New Nucleophilic Reagents for S_NAr Amination and Carbamoyl Amination Reactions in 1,3,7‐Triazapyrene Series

Боровлев

Демидов

Amangasieva

et al. 2016

Journal of Heterocyclic Chem

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The ability of urea anions to react as nucleophiles with alkoxy derivatives of 1,3,7‐triazapyrenes has been investigated. It was found that against all expectations, the products of the substitution of an alkoxy groups (SNipso) by amino group were isolated in good yields. The reactions proceed in anhydrous dimethyl sulfoxide solution at room temperature. But when anions of the mono‐substituted ureas containing bulky substituents were used, the first products of the earlier unknown SNAr reactions of alkyl carbamoyl amination were obtained.

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“…IR spectra were recorded on a Shimadzu IRTracer-100 as thin films. Starting compounds 1a,g, 40 1b,c, 26 1d,e, 25 and 1f 41 were obtained by known procedures. Sodium hydride as a 60% w/w dispersion in mineral oil was used as such (Merck).…”

Section: Methodsmentioning

confidence: 99%

Ureas as new nucleophilic reagents for SNH amination and carbamoyl amination reactions in the 1,3,7-triazapyrene series

Боровлев¹,

Демидов²,

Amangasieva³

et al. 2016

Arkivoc

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The ability of urea anions to react as nucleophiles with 1,3,7-triazapyrenes has been investigated. It was found that, against all expectations, the products of the substitution of hydrogen (S N H ) by an amino group were isolated in good yields. The reactions proceed in anhydrous DMSO solution at room temperature. However, when anions of mono substituted ureas containing bulky substituents were used, the products of previously unknown S N H reactions of alkyl carbamoyl amination were obtained.

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1,3,7-Triazapyrene: the first case of hetarylation of benzene and its analogs

Cited by 7 publications

References 7 publications

Synthesis of 2-Azapyrenes and Their Photophysical and Electrochemical Properties

Synthesis of 2-Azapyrenes and Their Photophysical and Electrochemical Properties

Ureas as a New Nucleophilic Reagents for S_NAr Amination and Carbamoyl Amination Reactions in 1,3,7‐Triazapyrene Series

Ureas as new nucleophilic reagents for SNH amination and carbamoyl amination reactions in the 1,3,7-triazapyrene series

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1,3,7-Triazapyrene: the first case of hetarylation of benzene and its analogs

Cited by 7 publications

References 7 publications

Synthesis of 2-Azapyrenes and Their Photophysical and Electrochemical Properties

Synthesis of 2-Azapyrenes and Their Photophysical and Electrochemical Properties

Ureas as a New Nucleophilic Reagents for SNAr Amination and Carbamoyl Amination Reactions in 1,3,7‐Triazapyrene Series

Ureas as new nucleophilic reagents for SNH amination and carbamoyl amination reactions in the 1,3,7-triazapyrene series

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Ureas as a New Nucleophilic Reagents for S_NAr Amination and Carbamoyl Amination Reactions in 1,3,7‐Triazapyrene Series