Methods of peri-annulation of five- and six-membered carbocyclic and nitrogen containing heterocyclic fragments

Аксенов, А. В.; Lyakhovnenko, A. S.; Aksenov, Nicolai A.; Аксенова, И. В.

doi:10.1134/s2079978012030016

Cited by 9 publications

(10 citation statements)

References 124 publications

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“…13 (8), 343 (M + , 34), 342 (29), 341 (M + , 100), 170 (22), 139 (16), 138 (11), 115 (17), 39 (15). HRMS (EI) m/z: [M + ] calcd for C 23 H 16 ClN 341.0966, found 341.0962, [M + ] calcd for C 23 H 16 37 ClN 343.0936, found 343.0939. 4-Chloro-3,5-bis(m-tolylethynyl)pyridine (2c).…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…1 H NMR (500 MHz, CDCl 3 ): δ 8.64 (s, 2H), 7.59 (dd, J = 8.6 Hz, J = 5.4 Hz, 4H), 7.09 (pt, J = 8.6 Hz, 4H). 13 (6), 351 (M + , 34), 350 (23), 349 (M + , 100), 286 (22), 174 (13), 144 (22), 143 (20), 75 (10), 57 The Journal of Organic Chemistry (8), 451 (M + , 35), 450 (25), 449 (M + , 100), 430 (10), 318 (13), 224 (12), 193 (10) (10), 375 (M + , 34), 374 (24), 373 (M + , 100), 358 (17), 251 (10), 224 (10), 187 (14), 143 (12), 99 (10) (13), 401 (M + , 37), 400 (30), 399 (M + , 100), 398 (37), 382 (13), 281 (12), 207 (12), 200 (24), 199 (15), 191 (10), 125 (11). HRMS (EI) m/z: [M + ] calcd for (8), 327 (M + , 43), 326 (20), 325 (M + , 100), 219 (11), 162 (13), 132 (12), 93 (10), 69 (15), 58 (16), 45 (57) 5, 129.7, 128.7, 128.3, 122.6, 119.3, 95.3, 85.7, 21.5.…”

Section: ■ Experimental Sectionmentioning

confidence: 99%

“…Synthetic strategies for the construction of azapyrenes have been previously reported on the basis of multistep procedures with a set of drawbacks, e.g., harsh conditions, expensive or complex starting materials, low selectivity, and only low functionalization potential. − With regard to 2-azapyrenes (naphtho[2,1,8- def ]isoquinolines), only the unsubstituted parent compound has been reported in the literature so far. 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 .…”

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: ■ Experimental Sectionmentioning

confidence: 99%

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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“…The incorporation of heteroatoms in PACs modifies the π–electron distribution, thus, leading to intriguing properties and potential applications . 1,2‐ or 1,3‐diazanaphthalenes, also known as perimidines or peridazines, respectively, as well as their acenaphth(yl)ene hetero analogues are major members of the group of peri ‐annelated heterocycles …”

Section: Introductionmentioning

confidence: 99%

“…Within the estimated chemical space, libraries of potentially useful drug leads have been and still are built up by diverse approaches , . Peri ‐fused N,O‐heterocycles, on the other hand, are much less known, . The 1,2‐oxazine core structure, for example, has been a long‐known research theme and its benzo analogue has also been targeted but to a limited extent ,,.…”

Section: Introductionmentioning

confidence: 99%

Naphthalene Peri Annelated N,N‐ and N,O‐Heterocycles: The Effect of Heteroatom‐Guided Peri‐Fusion on Their Structure and Reactivity Profiles‐A Theoretical Endoscopy

et al. 2018

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An endoscopy of the little known peri‐fused N,N and N,O‐heterocycles is described herein using the density functional theory (DFT/B3LYP), the 2nd order Møller–Plesset perturbation theory (MP2) and the 6–311++G(d,p) basis set. Their salient structure features, their reflection onto aromaticity, depicted by means of certain aromaticity indicators (HOMA, IA, ABO, PDI, FLU, NICS) and their reactivity profiles are the theme of this investigation. N and O atom(s) and their relative arrangement in the ring perturb the σ and π frames of the structures and ultimately introduce peri strain. The incorporation of N and O atoms in the annelated ring causes a limited π‐delocalization over the whole structure, a relatively low aromatic character and a weakly polarized double bond of the heteroring. Bond length variation, in the range of 0.01‐0.05 Å, dihedral angles deviating from planarity by 1.2‐4.1 Å and compressed fusion bonds, particularly peri ones, indicate a σ frame–triggered ring distortion of 0.6‐2.6° as an “outward” stretching of the lower part of a still planar structure except one. The heteroring, as a masked enamine, hydrazone, imine, vinyl ether, oxime or imino ether, clamped onto naphthalene scaffold, appears to be the best description of this type of structures. The nature of the heteroring dictates their reactivity profile. Those housing the masked hydrazine and oxime entities exhibit a “ring α‐effect”‐guided reactivity, consistent with preliminary experimental findings.

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Synthesis, Structures, and Optical Properties of Azahelicene Derivatives and Unexpected Formation of Azahepta[8]circulenes

Chen

Tanaka

Mori

et al. 2018

Chemistry A European J

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Polycyclic heteroaromatic compounds including pyrrole units are promising functional scaffolds owing to their electron-rich nature, bright fluorescence, and applicability to anion recognition at the pyrrolic hydrogen atom. We report herein the effective synthesis of pseudo-aza[5]helicene and aza[7]helicene derivatives, and unexpected formation of azahepta[8]circulenes by oxidative fusion reactions. By choosing reaction conditions and peripheral substituents attached at the terminal indole moieties, we obtained aza[7]helicenes 10 a-c and azahepta[8]circulenes 11 a,c selectively in moderate to good yields. Their solid-state structures have been revealed by X-ray diffraction analysis. UV/Vis absorption, emission, and cyclic voltammetry of these compounds were studied in comparison with those of previously reported tetraaza[8]circulene (TA8C), a symmetric and planar molecule. Furthermore, the enantiomeric separation of dimethyl-substituted aza[7]helicene 10 b was achieved, and the racemization kinetics have been elucidated both theoretically and experimentally. This work illustrates a wealth of advantages of pyrrole incorporation into the polycyclic aromatic scaffolds in terms of synthetic aspects, structural variation, and optical tuning.

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Methods of peri-annulation of five- and six-membered carbocyclic and nitrogen containing heterocyclic fragments

Cited by 9 publications

References 124 publications

Synthesis of 2-Azapyrenes and Their Photophysical and Electrochemical Properties

Synthesis of 2-Azapyrenes and Their Photophysical and Electrochemical Properties

Naphthalene Peri Annelated N,N‐ and N,O‐Heterocycles: The Effect of Heteroatom‐Guided Peri‐Fusion on Their Structure and Reactivity Profiles‐A Theoretical Endoscopy

Synthesis, Structures, and Optical Properties of Azahelicene Derivatives and Unexpected Formation of Azahepta[8]circulenes

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