A versatile strategy for the synthesis of functionalized 2,2 `-bi- and 2,2 `: 6 `,2 `'-terpyridines via their 1,2,4-triazine analogues / Kozhevnikov VN,Kozhevnikov DN,Nikitina TV,Rusinov VL,Chupakhin ON,Zabel M,Konig B // JOURNAL OF ORGANIC CHEMISTRY. - 2003. - V. 68, l. 7. - P. 2882-2888.

ISSN/EISSN:

0022-3263 / нет данных

Type:

Article

Abstract:

A general synthetic route for the synthesis of functionalized bi- and terpyridines is reported. Functionalized 1,2,4-triazene 4-oxides 7 and 8-obtained from the reaction of hydrazones 1 with pyridine aldehydes and followed by oxidation-are functionalized by introduction of a cyano group via nucleophilic aromatic substitution. The thus-obtained 5-cyano-1,2,4-triazines 9 and 10 undergo facile inverse-electron-demand Diels-Alder reactions with enamines and alkenes to yield functionalized bi- and terpyridines, respectively. The substituent at position 6 of the 1,2,4-triazene 4-oxides must be aromatic or heteroaromatic in order to allow their facile synthesis, but other substituents and reagents may vary. Each step of the synthetic route allows diversification, which makes the approach particularly useful for the facile synthesis of a large variety of functionalized bi- and terpyridines.

Author keywords:

FLUORESCENCE; BIPYRIDINE; ROUTE

DOI:

10.1021/jo0267955

Web of Science ID:

ISI:000181953700045

Соавторы в МНС:

Другие поля

Поле	Значение
Month	APR 4
Publisher	AMER CHEMICAL SOC
Address	1155 16TH ST, NW, WASHINGTON, DC 20036 USA
Language	English
Keywords-Plus	FLUORESCENCE; BIPYRIDINE; ROUTE
Research-Areas	Chemistry
Web-of-Science-Categories	Chemistry, Organic
Author-Email	kozhevnikov\_v@htf.ustu.ru dnk@htf.ustu.ru burkhard.koenig@chemie.uni-regensburg.de
ResearcherID-Numbers	Kozhevnikov, Valery/B-1178-2010 Koenig, Burkhard/A-1362-2009
ORCID-Numbers	Kozhevnikov, Valery/0000-0001-7032-8886 Koenig, Burkhard/0000-0002-6131-4850
Number-of-Cited-References	20
Usage-Count-Since-2013	12
Journal-ISO	J. Org. Chem.
Doc-Delivery-Number	662NM