Saturated heterocycles, 162 [1]. synthesis and steric structures of 3,4‐disubstituted 1,6,7,11b‐tetrahydropyrimido[6,1‐a]isoquinolin‐2‐ones | Zendy

Fulöp Ferenc | Zendy; Semega Eva | Zendy; Bernáth Gábor | Zendy; Sohár Pál | Zendy

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Saturated heterocycles, 162 [1]. synthesis and steric structures of 3,4‐disubstituted 1,6,7,11b‐tetrahydropyrimido[6,1‐a]isoquinolin‐2‐ones

Author(s) -

Fulöp Ferenc,

Semega Eva,

Bernáth Gábor,

Sohár Pál

Publication year - 1990

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.5570270425

Subject(s) - chemistry , stereospecificity , steric effects , yield (engineering) , reagent , ring (chemistry) , tetrahydroisoquinoline , hydrazone , stereochemistry , medicinal chemistry , organic chemistry , catalysis , materials science , metallurgy

The reaction of 1‐(hydrazidomethyl)‐6,7‐dimethoxy‐1,2,3,4‐tetrahydroisoquinoline 3 with aromatic aldehydes yield hydrazones 4a,b or pyrimido[6,1‐ a ]isoquinolines 5a‐c depending upon the proportions of the reagents. With ketones, 3 gives only hydrazones 4a‐d and 7 , which can be transformed to pyrimidoisoquinolines 10a‐e and 11 with aldehydes. The ring closures are stereospecific; the relative configurations were determined by DNOE measurements.

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