Gold‐Catalyzed Synthesis of 1,3‐Diaminopyrazoles from 1‐Alkynyltriazenes and Imines

Jeanbourquin, Loïc; Scopelliti, Rosario; Fadaei‐Tirani, Farzaneh; Severin, Kay

doi:10.1002/hlca.201700186

Cited by 12 publications

(5 citation statements)

References 34 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In an interesting approach toward the functionalization of alkynes, the group of Severin employed 1-alkynyltriazenes 108 and imines 109 as substrates in a gold-catalyzed synthesis of 1,3-diaminopyrazoles 110 (Scheme ). They found that 1-alkynyltriazenes can be activated by an electrophilic gold species in a manner similar to that of more traditional ynamides. To account for the formation of 110 , the authors proposed that imine 109 initially adds to Au(I)-activated alkynyltriazene 111 .…”

Section: Carbon π-Systems With Electron-donating Groupsmentioning

confidence: 99%

Gold-Catalyzed Reactions of Specially Activated Alkynes, Allenes, and Alkenes

et al. 2020

View full text Add to dashboard Cite

This review describes the gold-catalyzed reactions of specially activated alkynes, allenes, and alkenes. Such species are characterized by the presence of either electron-donating or electron-withdrawing groups as substituents of the carbon π-system. They are intrinsically polarized, and when compared to their nonspecially activated counterparts can therefore be involved in gold-catalyzed transformations featuring increased regio-, stereo-, and chemoselectivities. The chemistry of specially activated carbon π-systems under homogeneous gold catalysis is extremely rich and varied. The reactivity observed with nonspecially activated unsaturated systems can often be transposed to specially activated ones without loss of efficiency. However, specially activated carbon π-systems also exhibit specific reactivities that cannot be attained with regular substrates. In this family of carbon π-systems, ynamides and their analogs, along with alkynyl carbonyl derivatives, are the classes of substrates that have retained the most attention. This review provides an overview of the chemistry developed with all classes of specially activated carbon π-systems by discussing their general and specific reactivities, presenting and commenting on their gold-catalyzed transformations as well as their applications.

show abstract

Section: Carbon π-Systems With Electron-donating Groupsmentioning

confidence: 99%

Gold-Catalyzed Reactions of Specially Activated Alkynes, Allenes, and Alkenes

et al. 2020

View full text Add to dashboard Cite

show abstract

“…In the presence of gold catalysts, propargyl‐based alkynyl triazenes can undergo coupling reactions with imines to give 1,3‐diaminopyrazole derivatives in moderate to good yields (Scheme 8). [25] As in the case of the ZnCl 2 ‐induced rearrangement of allenyl triazenes (Scheme 7), the N 3 R 2 group is involved in the transformation. This finding shows that alkynyl triazenes can undergo transformations which are distinct from those of other activated alkynes such as ynamides.…”

Section: Alkynyl Triazenesmentioning

confidence: 99%

Vinyl and Alkynyl Triazenes: Synthesis, Reactivity, and Applications

Suleymanov

Severin

2020

Angewandte Chemie

Self Cite

View full text Add to dashboard Cite

Aromatic compounds containing triazenyl groups (N3RR′) have a profound impact on synthetic organic and medicinal chemistry. In contrast, the chemistry of vinyl and alkynyl triazenes was a largely uncharted territory until recently. The situation has changed over the last five years, and it has become apparent that vinyl and alkynyl triazenes are highly interesting compounds with a unique reactivity. The electron‐donating properties of the triazenyl group provide alkynyl triazenes with an ynamide‐like reactivity, which can be exploited in reactions of the triple bond. Vinyl triazenes, on the other hand, can be used for electrophilic vinylation reactions. The foundation for this new triazene chemistry are synthetic pathways which allow preparing vinyl and alkynyl triazenes in few steps from readily available starting materials. In this Minireview, we summarize recent developments in this area.

show abstract

“…Over the past years, the use of 1-alkynyl triazenes in organic synthesis has been receiving a growing interest. 12 a ,23,24 Leveraging on their ynamide-like reactivity profile, 25 we herein report three sets of convenient protocols that allow the fully chemo- and regio-divergent formations of tetrafluoro-alkyl triazenes, difluoro-alkyl triazenes and α-difluoro acyl triazenes from 1-alkynyl triazenes (Scheme 1c). Such fluorinated 1-alkyl and 1-acyl triazenes expand the chemical space for medicinal chemistry studies involving triazene molecules.…”

Section: Introductionmentioning

confidence: 99%