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New dehydration in the pyrrolo[1,2–6‐ b ]isoquinoline series. Preparation and structural identification of 3,5‐dihydrobenz[ f ]indolizin‐3‐one
Author(s) -
Rigo Benoít,
Tullier Etienne,
Barbry Didier,
Couturier Daniel,
Warin Vincent,
Lamiot Jocelyne,
Baert François
Publication year - 1990
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.5570270537
Subject(s) - chemistry , dehydration , isoquinoline , indolizine , dehydration reaction , nuclear magnetic resonance spectroscopy , stereochemistry , biochemistry
3,5‐Dihydrobenz[ f ]indolizin‐3‐one was prepared by a novel dehydration reaction involving the heating of 1,2,3,5,10,10a‐hexahydro[ f ]indolizine‐3,10‐dione with polyphosphoric acid. The structure of this new compound was established by X‐ray crystallography, by nmr spectroscopy and by reduction to the known products 1,2,3,5‐tetrahydrobenz[ f ]indolizin‐3‐one and 1,2,3,5,10,10a‐hexahydrobenz[ f ]indolizin‐3‐one.