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Intramolecular cyclizations leading to bridgehead bicyclics 2 . 5,5‐dialkylhydantoin derivatives
Author(s) -
Okada Katsuhide,
Kelley James A.,
Driscoll John. S.
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.5570140332
Subject(s) - chemistry , oxazole , alkylation , intramolecular force , bicyclic molecule , hydantoin , lactam , stereochemistry , mass spectrum , medicinal chemistry , organic chemistry , catalysis , ion
The effect of substituenls in the 5‐position on the course of hydantoin intramolecular alkylation reactions was studied. Dialkyl and diaryl substituted intermediates resulted in the same type product, 2,3‐dihydro‐6,6‐disubstituted imidazo[2,1‐ b ]oxazole‐5(6 H )ones, indicating alkylation on oxygen rather than nitrogen. The mass spectral and nmr characteristics of these bicyclic compounds are discussed.