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Quinazolines and 1,4‐benzodiazepines. LXXIII. The ring expansion of 2‐chloromethylquinazoline 3‐oxides with nitromethane
Author(s) -
Fryer R. Ian,
Earley James V.,
Gilman Norman W.,
Zally William
Publication year - 1976
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.5570130303
Subject(s) - nitromethane , chemistry , ring (chemistry) , halogen , nucleophile , medicinal chemistry , ion , organic chemistry , catalysis , alkyl
The reaction of 2‐chloromethylquinazoline 3‐oxides (3) with the anion of nitromethane gave the 2‐nitromethylene benzodiazepine oxides (4) as a result of ring expansion. Other nucleophiles led only to products derived from substitution of the halogen. The ring expansion of 2,2‐dichloro‐1,2‐dihydroquinazolines with nitromethane anion is also described.
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