TRIAZOLOPYRIDINES .16. LITHIATION OF 3-CYANO[1,2,3]TRIAZOLO[1,5-A]-PYRIDINE

Authors
JONES G MOUAT DJ PITMAN MA LUNT E LYTHGOE DJ
Citation
G. Jones et al., TRIAZOLOPYRIDINES .16. LITHIATION OF 3-CYANO[1,2,3]TRIAZOLO[1,5-A]-PYRIDINE, Tetrahedron, 51(40), 1995, pp. 10969-10978
Citations number
8
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
51
Issue
40
Year of publication
1995
Pages
10969 - 10978
Database
ISI
SICI code
0040-4020(1995)51:40<10969:T.LO3>2.0.ZU;2-I
Abstract
Various methods for the synthesis of 3-cyanotriazolopyridine 8 by diaz o transfer to 2-pyridylacetonitrile are described. Lithiation of the t riazolopyridine 8 using LDA or TMPA followed by quenching with TMS chl oride, gave the 4-mono-, the 7-mono-,and the 4,7- di TMS derivatives 1 4, 18, and 15, and the amidines 16 and 17, in contrast to the previous ly reported regiospecific attack at position 7. A Grignard reaction on compound 8 gave 3-propionyl triazolopyridine, 13.