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Thermolysis of the reaction products from 2‐pyridylacetohydrazide and nitrous acid
Author(s) -
Iwao Masatomo,
Kuraishi Tsukasa
Publication year - 1977
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570140609
Subject(s) - nitrous acid , chemistry , thermal decomposition , azide , decomposition , medicinal chemistry , nitrous oxide , alkali metal , organic chemistry
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)‐1,2,4‐4 H ‐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)