کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
5212308 1383111 2017 13 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
4-(Azulen-1-yl) six-membered heteroaromatics substituted in 2- and 6- positions with 2-(2-furyl)vinyl, 2-(2-thienyl)vinyl or 2-(3-thienyl)vinyl moieties
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
4-(Azulen-1-yl) six-membered heteroaromatics substituted in 2- and 6- positions with 2-(2-furyl)vinyl, 2-(2-thienyl)vinyl or 2-(3-thienyl)vinyl moieties
چکیده انگلیسی


- 2,6-(diheteroarylvinyl)-4-(azulen-1-yl) six-member heterocyclic compounds were synthesized.
- Discussion of the maxima of absorption based on the molecular calculus.
- Description of the isosbestic points, calculi of the pKa values and presentation of the solvatochromic effect.
- Interaction with metal ions.
- Comparative presentation of the oxidation and reduction potentials.

The synthesis of pyrylium and pyridinium salts and pyridines with azulene-1-yl moieties in position 4 and two 2-heteroarylvinyl groups in positions 2 and 6 was accomplished. The pyrylium salts were obtained starting from pyranones and pyridines could be prepared from these salts by treating them with ammonium acetate. The general procedures for the synthesis of pyridinium salts, which occur with good results in less delocalized electronic systems, do not take place when applied to the above obtained pyrylium salts. Therefore, as starting material 4-(azulen-1-yl)-1-(n-butyl)-2,6-dimethylpyridinium perchlorate was used, which was condensed with heteroarylcarboxaldehydes. These compounds were completely characterized and some of their spectra were discussed. Their interaction with some metal ions was revealed, observing an affinity better than in the case of simple azulenepyridines. In the last part of the paper are presented redox potentials for several pyrylium salts and pyridines in comparison with those of the nonvinylogated derivatives.

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ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Tetrahedron - Volume 73, Issue 17, 27 April 2017, Pages 2488-2500
نویسندگان
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