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8,11 a‐methanocycloocta[ d,e ]quinazolines: Diisophoranes incorporating the pyrimidine ring system
Author(s) -
Kurzer Frederick,
Langer Stanley S.
Publication year - 1989
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.5570260535
Subject(s) - chemistry , ring (chemistry) , pyrimidine , tricyclic , nucleophilic substitution , nucleophile , carbon skeleton , stereochemistry , spectral properties , medicinal chemistry , organic chemistry , computational chemistry , catalysis
The interaction of 1‐chloro(or hydroxy)diisophor‐2(7)‐en‐3‐one 1 or 3 with guanidines or ureas produces good yields of substituted 8,11a‐methanocycloocta[ d,e ]quinazolines 5‐11 , involving a nucleophilic SN 1 ‐substitution at the 1‐bridgehead and dehydrative cyclisation at the 3‐keto‐group of the tricyclic reactants 1, 3. The structure assigned to members of this novel heterocyclic bridged ring‐system is based on both chemical and carbon nmr spectral evidence. The synthesis provides further variants of the incorporation of a fused heterocyclic ring into the tricyclo[7.3.1.0 2,7 ]tridecane carbon skeleton. A related condensed [1,3]oxazine 16 is similarly accessible.