Synthesis of Pyridoisoindoles through Diazotization Followed by Intramolecular Cyclization from Pyridinylarylacetates in One Pot | Zendy

Kim CheolEui | Zendy; Baek Yonghyeon | Zendy; Kim Sung Hong | Zendy; Lee Phil Ho | Zendy

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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].

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