Modular synthesis of triazoles from 2-azidoacrylamides having a nucleophilic amino group

Abstract

Assembling methods using 2-azidoacrylamides having a nucleophilic amino group are disclosed. Divergent transformations of the amine-type trivalent platform were accomplished with a wide variety of electrophiles to provide a broad...

Chemoselective Reactions of Functionalized Sulfonyl Halides

“…Being a strong electron‐withdrawing group, the SO 2 F fragment is considered as one of the best double bond activators for the nucleophilic conjugate (Michael) addition [60] . Indeed, alkenyl sulfonyl fluorides readily react with a huge variety of C ‐, [60–64] N ‐, [43,62,64–67] S ‐, [25,64,67,68] or P ‐nucleophiles [69] (Scheme 4). For example, Michael addition to the simplest vinyl sulfonyl fluoride was used for the preparation of [ 18 F]‐labelled amino acids [70] and modification of s ‐tetrazine building blocks [71] .…”

Iterative click reactions using trivalent platforms for sequential molecular assembly

“…2 We have developed a variety of trivalent platforms for efficient molecular assembly by sequential click reactions. 3–5 In particular, we recently succeeded in the synthesis of trivalent platform 1a that served in the sequential click conjugation by the SuFEx reaction, 6 copper-catalyzed azide–alkyne cycloaddition (CuAAC), 7 and thia-Michael reaction, 8 where the triazole formation remarkably enhanced the Michael reactivity of acrylamides (Fig. 1B).…”

Click assembly through selective azaylide formation

“…Trivalent platforms having three clickable functional groups for assembling modules gain attention from diverse research fields including pharmaceutical sciences and chemical biology due to the great importance of multifunctional molecules. 1–4 Despite recent emerging advances in sequential click reactions, it is not easy to perform click assembly without deprotection due to the limited trivalent platforms. Herein, we disclose an efficient assembly of functional modules using a new trivalent platform through selective robust azaylide formations by Staudinger reaction.…”