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Reactivity of the Sultam and Strained Alkyne Groups in 2‐Aminobenzenesulfonamide‐Containing Cyclononyne (ABSACN)
Author(s) -
Kaneda Kyosuke,
Naruse Risa,
Yamamoto Syota,
Satoh Teppei
Publication year - 2018
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201700687
Subject(s) - alkyne , chemistry , reactivity (psychology) , cycloaddition , pyrrole , mitsunobu reaction , ring (chemistry) , reagent , click chemistry , combinatorial chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
2‐Aminobenzenesulfonamide‐containing cyclononyne (ABSACN), which is a heterocycle that contains a sultam and strained alkyne group within the same ring, exhibits remarkable chemical reactivity in processes such as pyrrole transformations, Pauson–Khand cyclizations, click reactions, and Mitsunobu condensations. Herein, we introduce the synthesis and reactions of ABSACN, which focus on the sultam and alkyne functional groups, and study the unique characterization of prepared ABSACN derivatives by NMR and X‐ray crystallographic analyses. This work could lead to the efficient production of pharmaceutically relevant multiheterocyclic systems by using sequential cycloaddition reactions. ABSACN can also serve as a potential template for multifunctional clickable alkyne reagents.