Synthesis of 2-Aminoimidazolones and Imidazolones by (3 + 2) Annulation of Azaoxyallyl Cations

DiPoto, Maria C.; Wu, Jimmy

doi:10.1021/acs.orglett.7b03719

Cited by 71 publications

(21 citation statements)

References 33 publications

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“…In their paper the authors demonstrated that the protection of indole was crucial to obtain (+/-)-minfiensine 126. While this type of cycloaddition has been extended to alkynes, 137 most of the efforts mainly focused on the cycloaddition with dipolarophiles bearing a heteroatom in the double (C=O, C=N, C=S) or the triple (C≡N) bond, to form 132 [138][139][140][141][142] by reaction with an aldehyde or a ketone, 131 [143][144] by reaction with an isothiocyanate or 129 and 130 145 by reaction with a nitrile. These reactions are mainly performed in fluorinated solvents such as HFIP.…”

Section: Aza-oxyallyl Cations In [3+2]-cycloadditions and Recent Devementioning

confidence: 99%

α-Halogenoacetamides: versatile and efficient tools for the synthesis of complex aza-heterocycles

2019

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Section: Aza-oxyallyl Cations In [3+2]-cycloadditions and Recent Devementioning

confidence: 99%

α-Halogenoacetamides: versatile and efficient tools for the synthesis of complex aza-heterocycles

2019

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“…Transition metal dialkylcyanamide complexes attract significant attention for the past decades due to structural features of NCNAlk 2 ligands, which is differ from those of conventional nitrile ligands NCR (R=Alk, Ar) . Moreover, coordinated dialkylcyanamides exhibit excitingly different reaction behavior as compared to the conventional nitrile ligands, and metal‐involving reactions of NCNR 2 ’s allow the atom‐economic synthesis of aminosubstituted five‐membered heterocycles, e. g. 5‐amino‐1,2,4‐oxadiazoles,, 5‐amino‐2,3‐dihydro‐1,2,4‐oxadiazoles,, 5‐aminotetrazoles, 2‐amionooxazoles, 2‐aminoimidazolones, and 1,2,4‐oxadiazol‐5‐imines, and six‐membered heterocycles, e. g. aminopyridines, and aminopyrimidines …”

Section: Introductionmentioning

confidence: 99%

Cyclometalated Iridium(III) Complexes Featuring Disubstituted Cyanamides

et al. 2018

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The neutral cyclometalated iridium(III) complexes [Ir(ppy) 2 Cl (NCNR 2 )] [ppy = 2-phenylpyridinato-C 2 ,N, R = Me 3 a, Et 3 b, 1 = 2 C 5 H 10 3 c] were prepared via the reaction of the chlorobridged dimer [Ir 2 (ppy) 4 (μ-Cl) 2 ] (1) with corresponding dialkylcyanamides NCNR 2 (2 a-c) and 3 a-c were isolated in 74-85% yields. The cationic cyclometalated iridium(III) complex [Ir (ppy) 2 (NCNMe 2 ) 2 ](OTf) (4) was obtained by replacement of chloride ligands with NCNMe 2 in 1 in the presence of AgOTf. UV/Vis absorption and emission properties of 3 a À c and 4 were studied; these complexes exhibit luminescence in the solid state upon photoexcitation (340 nm, 77 K). The characteristic feature of the X-ray structures of 3 a-c is a deviation of the fragment Ir-N-C from linearity by 13.8(5)-22.8(3)°. Quantum chemical DFT calculations and topological analysis of the electron density distribution within the formalism of Bader's theory (AIM method) performed for 3 a-c demonstrated that the Ir-N-C fragments in the optimized equilibrium structures of [Ir(ppy) 2 Cl(NCNR 2 )] significantly deviate from the linearity (by 19.8-30.7°) and indicated that the Ir-N contacts between the metal centers and dialkylcyanamide ligands are relatively weak (24-30 kcal/mol) and have a closed-shell dative interactions character. The charge decomposition analysis (CDA) shows existence of {M} ! L donation with almost negligible contribution of the {M}!L back-donation in 3 a-c.

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“…With regard to [3 + 2] cycloaddition processes, azaoxyallyl cation intermediates were key players in syntheses of γ-lactams, [208] pyrroloindolines, [209a- [212] imidazolones, [213] thiazolidin-4ones, [214] and oxazolidin-4-ones. [215a-e] On the other hand, azaoxyallyl cations were three-atom components in [3 + 1] cycloadditions with sulfur ylides giving βlactams (Scheme 192).…”

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confidence: 99%

The Fascinating Chemistry of α‐Haloamides

et al. 2020

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The aim of this review is to highlight the rich chemistry of α‐haloamides originally mainly used to discover new C−N, C−O and C−S bond forming reactions, and later widely employed in C−C cross‐coupling reactions with C(sp3), C(sp2) and C(sp) coupling partners. Radical‐mediated transformations of α‐haloamides bearing a suitable located unsaturated bond has proven to be a straightforward alternative to access diverse cyclic compounds by means of either radical initiators, transition metal redox catalysis or visible light photoredox catalysis. On the other hand, cycloadditions with α‐halohydroxamate‐based azaoxyallyl cations have garnered significant attention. Moreover, in view of the important role in life and materials science of difluoroalkylated compounds, a wide range of catalysts has been developed for the efficient incorporation of difluoroacetamido moieties into activated as well as unactivated substrates.

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Synthesis of 2-Aminoimidazolones and Imidazolones by (3 + 2) Annulation of Azaoxyallyl Cations

Cited by 71 publications

References 33 publications

α-Halogenoacetamides: versatile and efficient tools for the synthesis of complex aza-heterocycles

α-Halogenoacetamides: versatile and efficient tools for the synthesis of complex aza-heterocycles

Cyclometalated Iridium(III) Complexes Featuring Disubstituted Cyanamides

The Fascinating Chemistry of α‐Haloamides

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