Synthesis and structure of 3-(1-naphthylmethylene)-,3-(2-naphthylmethylene)-, 3-(9-anthrylmethylene)-, 3-(quinolin-5-ylmethylene)-, and 3-(quinoxalin-5-ylmethylene)-1,2-dihydro-3H-1,4-benzodiazepin-2-ones
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MELNIC, Elena; KRAVTSOV, Viktor; BACHINSKII, Sergey; ISHKOV, Yu.; PAVLOVSKY, Victor; ANDRONATI, Serghei. Synthesis and structure of 3-(1-naphthylmethylene)-,3-(2-naphthylmethylene)-, 3-(9-anthrylmethylene)-, 3-(quinolin-5-ylmethylene)-, and 3-(quinoxalin-5-ylmethylene)-1,2-dihydro-3H-1,4-benzodiazepin-2-ones. In: Materials Science and Condensed Matter Physics. Ediția a 9-a, 25-28 septembrie 2018, Chișinău. Chișinău, Republica Moldova: Institutul de Fizică Aplicată, 2018, p. 153.
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Materials Science and Condensed Matter Physics
Ediția a 9-a, 2018
Conferința "International Conference on Materials Science and Condensed Matter Physics"
Chișinău, Moldova, 25-28 septembrie 2018

Synthesis and structure of 3-(1-naphthylmethylene)-,3-(2-naphthylmethylene)-, 3-(9-anthrylmethylene)-, 3-(quinolin-5-ylmethylene)-, and 3-(quinoxalin-5-ylmethylene)-1,2-dihydro-3H-1,4-benzodiazepin-2-ones


CZU: 544+546+538.9
Pag. 153-153

Melnic Elena1, Kravtsov Viktor1, Bachinskii Sergey2, Ishkov Yu.3, Pavlovsky Victor2, Andronati Serghei2
 
1 Institute of Applied Physics,
2 A.V. Bogatsky Physico-Chemical Institute of the NAS of Ukraine,
3 Одеський національний університет імені І. І. Мечникова
 
Disponibil în IBN: 5 februarie 2019


Rezumat

The search on new candidates for selective ligands of benzodiazepine receptors, and potential analgesics, stimulate us to synthesize the naphthalide- and heteronaphthalide-1,4-benzodiazepines. Condensation of 1,4-benzodiazepin-2-one 1 with 1- and 2-naphthalene, 9-anthracene and a number of quinoline and quinoxaline carbaldehydes resulted in 3-substituted 1,4-benzodiazepin-2-ones 2- 10. The structure of compounds 2-10 was confirmed by mass spectrometry and 1H NMR spectroscopy, and for (3Z)-7-bromo-5-phenyl-3-(quinoxalin-5-ylmethylene)-1,3-dihydro-2H-1,4- benzodiazepin-2-one 10 also by the X-ray diffraction method. The compound 10 crystallizes in the triclinic P-1 space group, a=7.9689(6), b=10.8434(8), c=12.5840(9) Å; α=80.627(6), β=75.074(6), =81.439(6), V=1030.1(1) Å3, Z=2 with one molecule per asymmetric unit. The seven-membered benzodiazepine ring in the molecule has the boat conformation. The N(1)–H•••O=C(2)=2.893(4) Å hydrogen bonds unite the molecules into centrosymmetric dimer forming R22(8) supramolecular synthon. The double C2=O2, N4=C5, and C3=C12 bond distances are equal to 1.221 (3), 1.276 (3), and 1.342 (4) Å, respectively. The planar quinoxaline fragments of neighboring center-symmetry related molecules reside in parallel planes with interplanar separation 3.501 Å, nevertheless they do not revealed the pronounced stacking interaction: the shortest centroid•••centroid benzene/benzene and benzene/pyrazine distances equal 4.093 and 4.242 Å, respectively. The C-H•••N6= 3.397 Å interactions unite the dimeric associates in the chain along crystallographic axis c.  

BibTeX Export

@article{ibn_71603,
author = {Melnic, E.I. and Kravţov, V.H. and Bachinskii, S.Y. and Ishkov, Y.V. and Pavlovsky, V.I. and Andronati, S.A.},
title = {<p>Synthesis and structure of 3-(1-naphthylmethylene)-,3-(2-naphthylmethylene)-, 3-(9-anthrylmethylene)-, 3-(quinolin-5-ylmethylene)-, and 3-(quinoxalin-5-ylmethylene)-1,2-dihydro-3H-1,4-benzodiazepin-2-ones</p>},
collection = {Materials Science and Condensed Matter Physics},
year = {2018},
volume = {Ediția a 9-a},
pages = {153-153},
abstract = {(EN) <p>The search on new candidates for selective ligands of benzodiazepine receptors, and potential analgesics, stimulate us to synthesize the naphthalide- and heteronaphthalide-1,4-benzodiazepines. Condensation of 1,4-benzodiazepin-2-one <strong>1 </strong>with 1- and 2-naphthalene, 9-anthracene and a number of quinoline and quinoxaline carbaldehydes resulted in 3-substituted 1,4-benzodiazepin-2-ones <strong>2- 10</strong>. The structure of compounds <strong>2-10 </strong>was confirmed by mass spectrometry and 1H NMR spectroscopy, and for (3Z)-7-bromo-5-phenyl-3-(quinoxalin-5-ylmethylene)-1,3-dihydro-2H-1,4- benzodiazepin-2-one <strong>10 </strong>also by the X-ray diffraction method. The compound <strong>10 </strong>crystallizes in the triclinic <em>P-1 </em>space group, <em>a</em>=7.9689(6), <em>b</em>=10.8434(8), <em>c</em>=12.5840(9) &Aring;; &alpha;=80.627(6), <em>&beta;</em>=75.074(6), =81.439(6), <em>V</em>=1030.1(1) &Aring;3, Z=2 with one molecule per asymmetric unit. The seven-membered benzodiazepine ring in the molecule has the boat conformation. The N(1)&ndash;H&bull;&bull;&bull;O=C(2)=2.893(4) &Aring; hydrogen bonds unite the molecules into centrosymmetric dimer forming R22(8) supramolecular synthon. The double C2=O2, N4=C5, and C3=C12 bond distances are equal to 1.221 (3), 1.276 (3), and 1.342 (4) &Aring;, respectively. The planar quinoxaline fragments of neighboring center-symmetry related molecules reside in parallel planes with interplanar separation 3.501 &Aring;, nevertheless they do not revealed the pronounced stacking interaction: the shortest centroid&bull;&bull;&bull;centroid benzene/benzene and benzene/pyrazine distances equal 4.093 and 4.242 &Aring;, respectively. The C-H&bull;&bull;&bull;N6= 3.397 &Aring; interactions unite the dimeric associates in the chain along crystallographic axis <em>c</em>. &nbsp;</p>},
url = {https://ibn.idsi.md/vizualizare_articol/71603},
}