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Acid‐catalyzed rearrangements of 6‐( p ‐tolyhydrazino)‐2‐thiouraeil
Author(s) -
Wright G. E.,
Gambino J.
Publication year - 1979
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.5570160244
Subject(s) - chemistry , intramolecular force , catalysis , thiouracil , medicinal chemistry , diamine , stereochemistry , amino acid , organic chemistry , biochemistry , medicine , thyroid
The action of acid on 6‐( p ‐tolylhydrazino)‐2‐thiouracil gives appreciable amounts of the stable Fischer intermediate, 5‐(2 ‐amino‐5 ‐tolyl)‐6‐amino‐2‐thiouracil. This compound undergoes intramolecular cyclization at high temperatures, and represents the first reported isolation of a diamine intermediate derived from a Fischer‐type indolization reaction.