New Push-Pull Fluorophores on the Basis of 6-Alkoxy-2,2'-Bipyridines: Rational Synthetic Approach and Photophysical Properties

Savchuk, Maria I.; Khasanov, Albert F.; Kopchuk, Dmitry S.; Krinochkin, Alexey P.; Nikonov, Igor L.; Starnovskaya, Еkaterina S.; Shtaitz, Yaroslav K.; Коvalev, Igor S.; Zyryanov, Grigory V.; Чупахин, О. Н.

doi:10.1007/s10593-019-02495-5

Cited by 15 publications

(2 citation statements)

References 35 publications

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“…[3,4] The wide opportunities for the pre-functionalization of 1,2,4-triazine cycle by means of S N H /S N ipso reactions should be also considered. Thus, S N ipso reactions between 5cyano-1,2,4-triazines and various O-, N-, C-nucleophiles such as alcohols, [5] aliphatic and aromatic amines, [6] CÀ H-active compounds [7] etc. are widely used for the one-step obtaining 5-Nu-1,2,4-triazines.…”

Section: Introductionmentioning

confidence: 99%

Highly Regioselective Synthesis of 3,6‐Diaryl‐2‐(het)arylpyridines by aza‐Diels‐Alder Reactions between 6‐H‐1,2,4‐Triazine Dienes and 2‐Amino‐4‐aryloxazole‐Based Dienophiles

et al. 2023

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A solvent-free reaction between C6-unsubstituted 5-aryl-1,2,4triazines and 2-amino-4-aryloxazoles at high temperature was studied. The reaction proceeds via inverse electron demand aza-Diels-Alder reaction between the oxazole moiety as dienophile and the 1,2,4-triazine moiety as diene with the highly regioselective formation of 3,6-diarylpyridines in up to 60 % isolated yield. The structure of one of the key-products was proven by the X-ray diffraction analysis, and the mechanism of the transformation was proposed. The reaction proceeds well for both 6-aryl and 6-hetaryl-1,2,4-triazines in the presence of the electron acceptor substituent at the position 3. In the case of the donor substituent in position 3, the pyridine yields are significantly reduced. In the case of 5,6-nonsubstituted 1,2,4-triazines, the triazine cycle is degraded without product formation. The high regioselectivity of the reaction as well as solvent-free conditions are valuable advantages of the present synthetic approach.

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Section: Introductionmentioning

confidence: 99%

Highly Regioselective Synthesis of 3,6‐Diaryl‐2‐(het)arylpyridines by aza‐Diels‐Alder Reactions between 6‐H‐1,2,4‐Triazine Dienes and 2‐Amino‐4‐aryloxazole‐Based Dienophiles

et al. 2023

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“…This is due to the easy availability of 5-cyano-1,2,4-triazines obtained via the nucleophilic substitution of hydrogen process [6]. Thus, the possibility of the substitution of the C5-cyano group by the residues of such nucleophiles as alcohols [7][8][9], amines [7,10,11], anilines [12][13][14], lithiumcarboranes [15], various CH acid residues [16,17], hydrazides of carboxylic acids [18,19] etc. was demonstrated earlier.…”

Section: Introductionmentioning

confidence: 99%

A convenient synthetic approach to 5-(het)arylhydrazine substituted 1,2,4-triazines

et al. 2020

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Neutral Lanthanide Complexes of 3‐Aryl‐6‐(quinolin‐2‐yl)picolinic Acids: Synthesis and Photophysical Studies

et al. 2020

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A convenient synthetic method has been developed for the synthesis of 3‐aryl‐6‐(quinolin‐2‐yl)picolinic acids having a cyclopentene fragment condensed to the pyridine ring. In addition, based on these new ligands neutral lanthanide complexes were obtained, and their photophysical properties were studied. It was observed that newly obtained quinoline‐based chelates exhibited a significant bathochromic shift of their absorption maxima compared to the previously described chelates based on 5‐aryl‐2,2′‐bipyridines.

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New Push-Pull Fluorophores on the Basis of 6-Alkoxy-2,2'-Bipyridines: Rational Synthetic Approach and Photophysical Properties

Cited by 15 publications

References 35 publications

Highly Regioselective Synthesis of 3,6‐Diaryl‐2‐(het)arylpyridines by aza‐Diels‐Alder Reactions between 6‐H‐1,2,4‐Triazine Dienes and 2‐Amino‐4‐aryloxazole‐Based Dienophiles

Highly Regioselective Synthesis of 3,6‐Diaryl‐2‐(het)arylpyridines by aza‐Diels‐Alder Reactions between 6‐H‐1,2,4‐Triazine Dienes and 2‐Amino‐4‐aryloxazole‐Based Dienophiles

A convenient synthetic approach to 5-(het)arylhydrazine substituted 1,2,4-triazines

Neutral Lanthanide Complexes of 3‐Aryl‐6‐(quinolin‐2‐yl)picolinic Acids: Synthesis and Photophysical Studies

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