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Synthesis of Pyridoisoindoles through Diazotization Followed by Intramolecular Cyclization from Pyridinylarylacetates in One Pot
Author(s) -
Kim CheolEui,
Baek Yonghyeon,
Kim Sung Hong,
Lee Phil Ho
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201500433
Subject(s) - chemistry , trifluoromethanesulfonate , intramolecular force , diazo , azide , copper , catalysis , combinatorial chemistry , organic chemistry
A robust synthetic method for a variety of pyridoisoindoles from pyridinylarylacetates has been developed through diazotization using 4‐methylbenzenesulfonyl azide and 1,8‐diazabicyclo[5.4.0]undec‐7‐ene followed by intramolecular cyclization via elimination of a nitrogen molecule under copper(II) trifluoromethanesulfonate‐catalyzed conditions in a one‐pot process. The intramolecular cyclization also took place efficiently with diazo substrates to produce pyridoisoindoles in good to excellent yields under metal‐free conditions or catalytic conditions [1.0 mol% copper(II) trifluoromethanesulfonate, 25 °C].