β-(Cycloalkylamino)ethanesulfonyl azides as novel water-soluble reagents for the synthesis of diazo compounds and heterocycles
Sign Up to like & getrecommendations! Published in 2019 at "Chemistry of Heterocyclic Compounds"
DOI: 10.1007/s10593-019-02609-z
Abstract: Novel water-soluble sulfonyl azides were synthesized, which are basic by nature. The obtained compounds were used as donors of the diazo group in the diazo transfer reaction. Due to their good solubility in water and… read more here.
Keywords: novel water; water; water soluble; ethanesulfonyl azides ... See more keywords
Highly efficient Mukaiyama-Mannich addition of α-diazo silyl enolate with nitrones catalyzed by MgI2 etherate
Sign Up to like & getrecommendations! Published in 2020 at "Tetrahedron"
DOI: 10.1016/j.tet.2020.131167
Abstract: Abstract Functionalized diazo hydroxylamines are prepared by an efficient Mukaiyama-Mannich addition of α-diazo silyl enolate with nitrones under mild reaction conditions. This protocol provides a variety of 1,2-addition adducts in good to excellent yields, which… read more here.
Keywords: mukaiyama mannich; efficient mukaiyama; addition; mannich addition ... See more keywords
N-Triftosylhydrazones: A New Chapter for Diazo-Based Carbene Chemistry.
Sign Up to like & getrecommendations! Published in 2022 at "Accounts of chemical research"
DOI: 10.1021/acs.accounts.2c00186
Abstract: ConspectusOver recent decades, N-sulfonylhydrazones have attracted significant attention in academic and industrial contexts owing to their ease of preparation, versatile reactivity, high stability, and practicality. In particular, the use of N-sulfonylhydrazones as precursors for diazo… read more here.
Keywords: chemistry; carbene chemistry; organic reactions; diazo ... See more keywords
Tumor-Targeted Delivery of 6-Diazo-5-oxo-l-norleucine (DON) Using Substituted Acetylated Lysine Prodrugs.
Sign Up to like & getrecommendations! Published in 2019 at "Journal of medicinal chemistry"
DOI: 10.1021/acs.jmedchem.8b02009
Abstract: 6-Diazo-5-oxo-l-norleucine (DON) is a glutamine antagonist with robust anticancer efficacy; however, its therapeutic potential was hampered by its biodistribution and toxicity to normal tissues, specifically gastrointestinal (GI) tissues. To circumvent DON's toxicity, we synthesized a… read more here.
Keywords: diazo oxo; oxo norleucine; diazo; tumor targeted ... See more keywords
Probing the Mechanism of Photoaffinity Labeling by Dialkyldiazirines through Bioorthogonal Capture of Diazoalkanes.
Sign Up to like & getrecommendations! Published in 2020 at "Organic letters"
DOI: 10.1021/acs.orglett.0c02714
Abstract: Dialkyldiazirines have emerged as reagents of choice for biological photoaffinity labeling studies. The mechanism of crosslinking has dramatic consequences for biological applications where instantaneous labeling is desirable, as carbene insertions display different chemoselectivity and are… read more here.
Keywords: mechanism photoaffinity; probing mechanism; photoaffinity; diazo ... See more keywords
Cu(I)-Catalyzed Coupling and Cycloisomerization of Diazo Compounds with Terminal Yne-Alkylidenecyclopropanes: Synthesis of Functionalized Cyclopenta[ b]naphthalene Derivatives.
Sign Up to like & getrecommendations! Published in 2018 at "Organic letters"
DOI: 10.1021/acs.orglett.8b01812
Abstract: A Cu(I)-catalyzed coupling and cycloisomerization of diazo compounds with terminal yne-alkylidenecyclopropanes (ACPs) has been presented. This reaction starts from the formation of an allenic intermediate in the Cu(I)-catalyzed cross-coupling reaction of a diazo compound with… read more here.
Keywords: coupling cycloisomerization; cycloisomerization diazo; yne; cycloisomerization ... See more keywords
Chiral Nickel(II) Complex Catalyzed Enantioselective Doyle-Kirmse Reaction of α-Diazo Pyrazoleamides.
Sign Up to like & getrecommendations! Published in 2018 at "Journal of the American Chemical Society"
DOI: 10.1021/jacs.7b12486
Abstract: Although high enantioselectivity of [2,3]-sigmatropic rearrangement of sulfonium ylides (Doyle-Kirmse reaction) has proven surprisingly elusive using classic chiral Rh(II) and Cu(I) catalysts, in principle it is due to the difficulty in fine discrimination of the… read more here.
Keywords: enantioselective doyle; kirmse reaction; doyle kirmse; nickel complex ... See more keywords
Rh(i)-Catalyzed intramolecular [2 + 2 + 1] cycloaddition of diynes with the N-terminal of the diazo group
Sign Up to like & getrecommendations! Published in 2019 at "Organic Chemistry Frontiers"
DOI: 10.1039/c9qo00403c
Abstract: A Rh(i) catalyzed [2 + 2 + 1] cycloaddition of intramolecular diynes and a diazo moiety has been reported, in which the dediazoniation does not occur and the terminal nitrogen of the diazo moiety serves… read more here.
Keywords: diynes terminal; diazo; cycloaddition; catalyzed intramolecular ... See more keywords
Iron catalysts with N-ligands for carbene transfer of diazo reagents.
Sign Up to like & getrecommendations! Published in 2020 at "Chemical Society reviews"
DOI: 10.1039/d0cs00221f
Abstract: Transition-metal-catalyzed carbene transfer reactions, involving diazo compounds and their precursors, are powerful tools for creating new C-C bonds. Depending on the involved catalytic system, the carbene insertion can efficiently be driven towards a specific functional… read more here.
Keywords: iron catalysts; carbene transfer; diazo; catalysts ligands ... See more keywords
Exploiting the umpolung reactivity of diazo groups: direct access to triazolyl-azaarenes from azaarenes.
Sign Up to like & getrecommendations! Published in 2022 at "Chemical communications"
DOI: 10.1039/d2cc01897g
Abstract: The present work documents electrophilic substitution of azaarenes, mainly isoquinolines, with hypervalent iodine diazo reagents (HIDR) followed by formal [3+2]-dipolar cycloaddition in a tandem fashion. Other azaarenes viz. pyridines and phenanthridines too could be successfully… read more here.
Keywords: reactivity diazo; triazolyl azaarenes; exploiting umpolung; umpolung reactivity ... See more keywords