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First Examples of Povarov Reaction of Cyclopentadienones
Author(s) -
Benmeddah Amel,
Bar Nathalie,
Villemin Didier,
Lohier JeanFrançois,
MostefaKara Bachir,
Legay Rémi
Publication year - 2018
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201800023
Subject(s) - quinoline , chemistry , regioselectivity , trifluoroacetic acid , formaldehyde , medicinal chemistry , organic chemistry , catalysis
We describe herein the first examples of Povarov reaction of tetrasubstituted cyclopentadienones in the preparation of quinoline compounds. Polycyclic compounds bearing tetrahydro‐3 H ‐cyclopenta[ c ]quinoline and dihydro‐1 H ‐cyclopenta[ c ]naphtha[2,3‐ h ]quinoline moieties have been synthesized by one pot reaction of tetrasubstituted cyclopentadienones with N ‐arylamines and formaldehyde in the presence of trifluoroacetic acid. The control of the regioselectivity was total as well with symmetrical and non symmetrical cyclopentadienones. The X‐ray structures of new quinolines were reported.