Abstract:
Benzylic oxidation of pinopyridine with SeO2 affords the corresponding keto derivative (71% yield) whose reductive amination with o- and p-anisidines proceeds stereoselectively to give 8R-amino derivatives; the reaction with o-phenylenediamine results in achiral pyridophenazine derivative possessing intense blue fluorescence at 441nm. Structures of o-anisidine derivative and substituted pyridophenazine have been characterized by X-ray crystallography.
Document Type:
Article
Language: English
Citation:
E. S. Vasilyev, A. M. Agafontsev, V. D. Kolesnik, Yu. V. Gatilov, A. V. Tkachev, “Stereoselective functionalisation of pinopyridine with anisidines and o-phenylenediamine”, Mendeleev Commun., 21:5 (2011), 253–255
Linking options:
https://www.mathnet.ru/eng/mendc2934
https://www.mathnet.ru/eng/mendc/v21/i5/p253
This publication is cited in the following 4 articles:
Diana Yu. Pobedinskaya, Oleg P. Demidov, Ivan V. Borovlev, Elena K. Avakyan, Gulminat A. Amangasieva, “Synthesis of pyrido[2,3-a]phenazines by intramolecular cyclization of 7-arylamino-8-nitrosoquinolines”, Chem Heterocycl Comp, 55:7 (2019), 684
E. S. Vasilyev, I. Yu. Bagryanskaya, A. V. Tkachev, “Syntheses of chiral nopinane-annelated pyridines of C2 and D2-symmetry: X-ray structures of the fused derivatives of 4,5-diazafluorene, 4,5-diaza-9H-fluoren-9-one, and 9,9'-bi-4,5-diazafluorenylidene”, Mendeleev Commun., 27:2 (2017), 128–130
Stanislav V. Larionov, Tatyana E. Kokina, Victor F. Plyusnin, Lyudmila A. Glinskaya, Alexey V. Tkachev, Yuliya A. Bryleva, Nataliya V. Kuratieva, Mariana I. Rakhmanova, Evgene S. Vasilyev, “Synthesis, structure and photoluminescence of Zn(II) and Cd(II) complexes with pyridophenazine derivative”, Polyhedron, 77 (2014), 75
Eugene S. Vasilyev, Alexander M. Agafontsev, Vasilij D. Kolesnik, Yurii V. Gatilov, Alexey V. Tkachev, “ChemInform Abstract: Stereoselective Functionalization of Pinopyridine with Anisidines and o‐Phenylenediamine.”, ChemInform, 43:10 (2012)
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