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Premium Terminal Acetylenic Iminium Salts: Cycloaddition Reactions with Azides Leading to 1,2,3‐Triazoles and Bicyclic 1,2,3‐Triazolium Salts
Author(s)
Keim Michael,
Maas Gerhard
Publication year2019
Publication title
european journal of organic chemistry
Resource typeJournals
PublisherWiley
Terminal acetylenic iminium triflate salts [HC≡C‐C(R)=N + Me 2 TfO – ] represent very potent dipolarophiles which undergo [3+2] cycloadditions with aryl and benzyl azides at very mild and uncatalyzed conditions, yielding 1,4‐disubstituted 1,2,3‐triazoles with complete regioselectivity. Addition of nucleophiles at the iminium group of the cycloadducts leads to diverse 1‐aryl‐(or benzyl‐)‐4‐dimethylaminomethyl‐1,2,3‐triazoles. The first formed cycloaddition adducts subsequently react with a second molecule of the acetylenic iminium salt by a consecutive Michael addition/1,5‐cyclization to form 2,4‐dihydropyrrolo[1,2‐ c ][1,2,3]triazol‐7‐ium triflates. Further transformations of the latter salts are described, among them the conversion into a mesoionic carbene, isolated as a monomeric silver(I) complex.
Subject(s)bicyclic molecule , catalysis , chemistry , combinatorial chemistry , computer science , cycloaddition , iminium , medicinal chemistry , organic chemistry , telecommunications , terminal (telecommunication)
Language(s)English
SCImago Journal Rank0.825
H-Index155
eISSN1099-0690
pISSN1434-193X
DOI10.1002/ejoc.201801749

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