Premium
Two Novel Thermal Biradical Cyclizations in Theory and Experiment: New Synthetic Routes to 6 H ‐Indolo[2,3‐ b ]quinolines and 2‐Aminoquinolines from Enyne‐Carbodiimides
Author(s) -
Schmittel Michael,
Steffen JensPeter,
Engels Bernd,
Lennartz Christian,
Hanrath Michael
Publication year - 1998
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/(sici)1521-3773(19980918)37:17<2371::aid-anie2371>3.0.co;2-n
Subject(s) - enyne , regioselectivity , alkyne , chemistry , aminoquinolines , hydrogen atom , medicinal chemistry , stereochemistry , combinatorial chemistry , organic chemistry , catalysis , alkyl
The regioselectivity of the biradical cyclization of enyne‐carbodiimides 1 can easily be controlled by variation of R 1 at the alkyne terminus. Attachment of a hydrogen atom (R 1 =H) leads to C 2 –C 7 cyclization and formation of biradical 2 , whereas C 2 –C 6 cyclization to provide biradical 3 is observed with R 1 =Me 3 Si or Ph.