A new method for [c,d]pyridine peri-annelation: synthesis of azapyrenes from phenalenes and their dihydro derivatives

Аксенов, А. В.; Боровлев, И. В.; Аксенова, И. В.; Писаренко, С. В.; Kovalev, Dmitry

doi:10.1016/j.tetlet.2007.11.132

Cited by 51 publications

(30 citation statements)

References 13 publications

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“…High-resolution mass spectra (HRMS) were registered with a Bruker UHR-TOF Maxis™ Impact instrument using the ESI technique. Starting compounds 1a, b, [22] c, d [9e] ,e, f [9d] and 6a, 6b [9b] 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%

S_N^H‐ and S_N^ipso‐Arylamination of 1,3,7‐Triazapyrenes

et al. 2014

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The ability of the oxidative arylamination process to derivatize electron‐deficient 1,3,7‐triazapyrenes has been investigated. These triazapyrenes react with a wide range of sodium aryl(hetaryl) amides to give access to the corresponding 6‐aryl(hetaryl)amino‐1,3,7‐triazapyrenes in moderate to good yields. The reaction of 6,8‐dialkoxy‐1,3,7‐triazapyrene with sodium arylamides gives rise to 6,8‐bis(arylamino)‐1,3,7‐triazapyrenes or 6‐methoxy‐8‐arylamino‐1,3,7‐triazapyrenes, depending on the reaction conditions.

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Section: Methodsmentioning

confidence: 99%

S_N^H‐ and S_N^ipso‐Arylamination of 1,3,7‐Triazapyrenes

et al. 2014

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“…Microanalyses were carried out on a CHN-1 Elemental Analyzer. Compounds 1a,b were obtained by a known procedure [7]. Other chemicals used in this study were commercially available.…”

Section: Methodsmentioning

confidence: 99%

An oxidative alkylamination of 1,3,7‐triazapyrenes in the aqueous medium

Боровлев

Демидов

Saigakova

et al. 2011

Journal of Heterocyclic Chem

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“…In studying the reactivity of 1,3,7-triazapyrenes [8] relative to nucleophiles we unexpectedly found that they very readily undergo a double alkoxylation under unusual conditions. Reaction of 1,3,7-triazapyrene (1a) and its 2-methyl-substituted 1b with excess KOH and K 3 Fe(CN) 6 in aqueous methanol solution occurs at room temperature to give a high yield of the previously unknown 6,8-dimethoxy derivatives of this heterocycle (2a and 2b respectively).…”

mentioning

confidence: 99%

Oxidative S N H-alkoxylation of 1,3,7-triazapyrenes

Демидов

Боровлев

Писаренко

et al. 2010

Chem Heterocycl Comp

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The classic strategies for synthesizing alkoxy derivatives of nitrogen heterocycles are based on the nucleophilic substitution of good leaving groups. Among these are also nonoxidative methods occurring via a tele-mechanism. Hence heteroarenes with di-or trichloromethyl substituents react with alkoxide anions to give products of substitution of hydrogen in the ring by an alkoxy group [1][2][3][4].In the case of electron-deficient aza aromatic substrates a better alternative can be a direct oxidative nucleophilic substitution of hydrogen (ONSH [5]) by an alkoxy group since it does not need the preliminary introduction of good nucleofuges into the molecule. However, in the literature there are only individual examples of the successful alkoxylation of heterocycles via the ONSH process [6,7].In studying the reactivity of 1,3,7-triazapyrenes [8] relative to nucleophiles we unexpectedly found that they very readily undergo a double alkoxylation under unusual conditions. Reaction of 1,3,7-triazapyrene (1a) and its 2-methyl-substituted 1b with excess KOH and K 3 Fe(CN) 6 in aqueous methanol solution occurs at room temperature to give a high yield of the previously unknown 6,8-dimethoxy derivatives of this heterocycle (2a and 2b respectively). A similar reaction with 1a and ethyl or propyl alcohols gave the 6,8-diethoxy-(2c) and 6,8-dipropoxy-1,3,7-triazapyrene (2d). N N N R N N N R OR 1 1a,b R 1 OH, H 2 O KOH, K 3 Fe(CN) 6 2a-d R 1 O 2 a R = H, R 1 = Me (98%), b R = R 1 = Me (89%), c R = H, R 1 = Et (91%), d R = H, R 1 = Pr (69%)

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A new method for [c,d]pyridine peri-annelation: synthesis of azapyrenes from phenalenes and their dihydro derivatives

Cited by 51 publications

References 13 publications

S_N^H‐ and S_N^ipso‐Arylamination of 1,3,7‐Triazapyrenes

S_N^H‐ and S_N^ipso‐Arylamination of 1,3,7‐Triazapyrenes

An oxidative alkylamination of 1,3,7‐triazapyrenes in the aqueous medium

Oxidative S N H-alkoxylation of 1,3,7-triazapyrenes

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A new method for [c,d]pyridine peri-annelation: synthesis of azapyrenes from phenalenes and their dihydro derivatives

Cited by 51 publications

References 13 publications

SNH‐ and SNipso‐Arylamination of 1,3,7‐Triazapyrenes

SNH‐ and SNipso‐Arylamination of 1,3,7‐Triazapyrenes

An oxidative alkylamination of 1,3,7‐triazapyrenes in the aqueous medium

Oxidative S N H-alkoxylation of 1,3,7-triazapyrenes

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S_N^H‐ and S_N^ipso‐Arylamination of 1,3,7‐Triazapyrenes

S_N^H‐ and S_N^ipso‐Arylamination of 1,3,7‐Triazapyrenes