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Synthesis of fused hydantoins by intramolecular amidoalkylation
Author(s) -
Zaugg H. E.,
Arendsen D. L.
Publication year - 1974
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.5570110526
Subject(s) - chemistry , halogenation , intramolecular force , ring (chemistry) , catalysis , medicinal chemistry , chloride , organic chemistry , combinatorial chemistry , stereochemistry
Several 1‐(2‐arylcthyl)hydantoins 2 have been cyclized through their 5‐bromo derivatives. The hydantoins 2a and 2b , unsubstituted in the 5‐posilion, require stannic chloride catalysis of the cyclization to 3a and 3b , respectively. However, the 5‐phenyl analog 2c (n = 2) cyclizes spontaneously and essentially quantitatively to 5 during bromination. This reaction is limited to the formation of a 6‐membered ring.
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