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Synthesis of 1,3,4‐Trisubstituted Isoquinolines by Iodine‐Mediated Electrophilic Cyclization of 2‐Alkynyl Benzyl Azides
Author(s) -
Fischer Dirk,
Tomeba Hisamitsu,
Pahadi Nirmal K.,
Patil Nitin T.,
Yamamoto Yoshinori
Publication year - 2007
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/anie.200701392
Subject(s) - electrophile , reagent , iodine , chemistry , combinatorial chemistry , substrate (aquarium) , organic chemistry , catalysis , oceanography , geology
The I's have it : A series of 2‐alkynyl benzyl azides have been smoothly converted into 1,3,4‐trisubstituted isoquinolines in moderate to excellent yields by an iodonium‐mediated synthesis (see scheme). Depending on the structure of the substrate, iodine, Barluenga reagent (Py 2 IBF 4 /HBF 4 ), or N ‐iodosuccinimide has been employed as the I + source.