Thermolysis of the reaction products from 2‐pyridylacetohydrazide and nitrous acid
- 1 October 1977
- journal article
- research article
- Published by Wiley in Journal of Heterocyclic Chemistry
- Vol. 14 (6) , 993-996
- https://doi.org/10.1002/jhet.5570140609
Abstract
2,3‐Dihydroimidazo[1,5‐α]pyridin‐3‐one (IV) was obtained by thermolysis of 2‐pyridylacetyl azide (II) which was prepared from 2‐pyridylacetohydrazide (I) on treatment with an equivalent mole of nitrous acid. Treatment of I with excess nitrous acid yielded α‐oximino‐α:‐(2‐pyridyl)‐acetylazide (V). Thermal decomposition of V gave 3‐(2‐pyridyl)‐1,2,4‐4H‐oxadiazolin‐5‐one (VII). 2‐Cyanopyridine (IX) was obtained from V by the action of alkali. 2,3‐Dihydroimidazo‐[1,5‐α ]pyridin‐3‐one (IV) was rearranged to VII upon treatment with nitrous acid. J. Chem. Soc., 14, 993 (1977)Keywords
This publication has 7 references indexed in Scilit:
- The oxidation of s‐triazolo[4,3‐b]pyridazines with selenium dioxideJournal of Heterocyclic Chemistry, 1976
- Kondensierte Isochinoline, XI. Imidazo[5,1‐a]isochinolineEuropean Journal of Inorganic Chemistry, 1975
- Imidazo[1,5-a]pyrazine systemThe Journal of Organic Chemistry, 1973
- The conversion of imidazo[1,5-a]pyridines into 3-(2-pyridyl)-1,2,4-oxadiazolesThe Journal of Organic Chemistry, 1967
- The tautomerism of heteroaromatic compounds with five-membered rings—VIIITetrahedron, 1965
- Notes - PyridineamidoximesThe Journal of Organic Chemistry, 1957
- Heterocyclic systems related to pyrrocoline. Part I. 2: 3a-DiazaindeneJournal of the Chemical Society, 1955