Stereoselective functionalisation of pinopyridine with anisidines and o-phenylenediamine

Stereoselective functionalisation of pinopyridine with anisidines and o-phenylenediamine Full article

Journal

Mendeleev Communications
ISSN: 0959-9436

Output data

Year: 2011, Volume: 21, Number: 5, Pages: 253-255 Pages count : DOI: 10.1016/j.mencom.2011.09.007

Authors

Vasilyev Eugene S. ¹ , Agafontsev Alexander M. ¹ , Kolesnik Vasilij D. ¹ , Gatilov Yurii V. ¹ , Tkachev Alexey V. ^1,2

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Dept Nat Sci, Novosibirsk 630090, Russia

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 441 nm. Structures of o-anisidine derivative and substituted pyridophenazine have been characterized by X-ray crystallography.

Vasilyev E.S. , Agafontsev A.M. , Kolesnik V.D. , Gatilov Y.V. , Tkachev A.V.
Stereoselective functionalisation of pinopyridine with anisidines and o-phenylenediamine
Mendeleev Communications. 2011. V.21. N5. P.253-255. DOI: 10.1016/j.mencom.2011.09.007 WOS Scopus РИНЦ

Published print:

Sep 1, 2011

Web of science	WOS:000296933500007
Scopus	2-s2.0-80053902250
Elibrary	18008724
OpenAlex	W2952097506