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Benzyne‐Induced Ring Opening Reactions of DABCO: Synthesis of 1,4‐Disubstituted Piperazines and Piperidines
Author(s) -
Seo Jeongseob,
Kim Daegeun,
Ko Haye Min
Publication year - 2020
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.202000375
Subject(s) - dabco , chemistry , aryne , moiety , nucleophile , octane , ring (chemistry) , combinatorial chemistry , amine gas treating , medicinal chemistry , stereochemistry , organic chemistry , catalysis
Abstract The 2‐(4‐phenylpiperazin‐1‐yl)ethan‐1‐amine scaffold is a structurally important motif that occurs frequently in medicinal and pharmaceutical chemistry. Despite the significance of this moiety, general strategies for its synthesis to date have required multistep methods and have been very limited, such as the use of S N Ar‐type reactions. Herein, we describe a synthetic methodology employing benzynes, 1,4‐diazabicyclo(2.2.2)octane (DABCO), and nitrogen nucleophiles to access these privileged organic compounds. The established protocol proved to be a transition‐metal‐free, mild reaction that proceeded via a quaternary ammonium salt formed from the benzyne and DABCO.