Synthesis of 4‐Aminopyrimidines from 1,2,4‐Oxadiazoles, II A General Method for the Preparation of 4‐Substituted 6,7‐Dihydro‐9,10‐dialkoxy‐2H‐pyrimido[6,1‐a]isoquinolin‐2‐imine Hydrochlorides

Dezső Korbonits, PÁL Kiss, Imre Bata, Gergely Héja, KáLmáN Simon, P. Kolonits

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5′‐Substituted 1‐[(1,2,4‐oxadiazol‐3‐yl)methyl]‐3,4‐dihydroisoquinolines (7) were reduced by NaBH4selectively to give the corresponding tetrahydroisoquinolines (8) which underwent ring isomerization to pyrazolo[5,1‐a]isoquinolines (9). Catalytic hydrogenation of 7 in the presence of hydrogen chloride, in turn, gave by reductive cleavage of the N–O bond of the 1,2,4‐oxadiazole ring and subsequent dehydration, quite generally, 4‐substituted pyrimido[6,1‐a]isoquinolin‐2‐imine hydrochlorides (11).

Original languageGerman
Pages (from-to)1039-1043
Number of pages5
JournalChemische Berichte
Issue number6
Publication statusPublished - 1987

ASJC Scopus subject areas

  • Chemistry(all)

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