Apparent Alkyl Transfer and Phenazine Formation via an Aryne Intermediate

Panagopoulos, Andria M.; Steinman, Doug; Goncharenko, Alexandra; Geary, Kyle; Schleisman, Carlene; Spaargaren, Elizabeth; Zeller, Mat­thias; Becker, Daniel P.

doi:10.1021/jo302795w

Cited by 11 publications

(4 citation statements)

References 30 publications

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“…Yield: 52%, orange crystals, mp. 79-80 °C, purification: silica gel 60, petroleum ether/ethyl acetate 9:1, analytical data are in complete accordance with literature values [40].…”

Section: General Procedures For the Synthesis Of 29 And 30supporting

confidence: 85%

Synthesis and in Silico Evaluation of Novel Compounds for PET-Based Investigations of the Norepinephrine Transporter

et al. 2015

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Since the norepinephrine transporter (NET) is involved in a variety of diseases, the investigation of underlying dysregulation-mechanisms of the norepinephrine (NE) system is of major interest. Based on the previously described highly potent and selective NET ligand 1-(3-(methylamino)-1-phenylpropyl)-3-phenyl-1,3-dihydro-2H-benzimidaz-ol-2-one (Me@APPI), this paper aims at the development of several fluorinated methylaminebased analogs of this compound. The newly synthesized compounds were computationally

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“…Yield: 52%, orange crystals, mp. 79-80 °C, purification: silica gel 60, petroleum ether/ethyl acetate 9:1, analytical data are in complete accordance with literature values [40].…”

Section: General Procedures For the Synthesis Of 29 And 30supporting

confidence: 85%

Synthesis and in Silico Evaluation of Novel Compounds for PET-Based Investigations of the Norepinephrine Transporter

et al. 2015

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“…The analysis data were consistent with those in a previous report. 61 Synthesis of 2-c (C 6 H 5 -NMe-C 6 H 4 -NH 2 ). SnCl 2 (91.2 g, 0.48 mol), 2-b (13.7 g, 0.06 mol), hydrochloric acid (100 mL, 37 wt%) and anhydrous ethanol (80 mL) were added to a round bottom flask of 1000 mL capacity.…”

Section: General Considerationsmentioning

confidence: 99%

“…The analysis data were consistent with a previous report. 61 Synthesis of ligand 2-L. 3,5-Di-tert-butylsalicylaldehyde (10.0 g, 43.0 mmol) was slowly added to a methanol solution of 2-c (8.30 g, 42.0 mmol) with 0.060 g of p-TsOH as a catalyst. The reaction mixture was stirred at room temperature for 24 h to produce a yellow suspension which was concentrated and filtered to give 2-L as a yellow solid (14.80 g, 35.7 mmol, 85% yield).…”

Section: General Considerationsmentioning

confidence: 99%

Influence of the N–H functionality on activating O,N,N-titanium complexes and controlling polyethylene molecular weights and distributions

Tian,

Gao,

Liu

et al. 2024

Inorg. Chem. Front.

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“…We therefore pursued deprotonation of L1, followed by transmetallation with iron halide, which was promising in producing paramagnetic products, but the mixtures were intractable. The formation of multiple species could be attributed, at least in part, to the deprotonated ligand undergoing a Smiles rearrangement (Panagopoulos et al, 2013).…”

Section: Synthesis Of Iron(ii) Complexesmentioning

confidence: 99%

Iron(II) complexes of dimethyltriazacyclophane

et al. 2018

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Treatment of the ortho-triazacyclophane 1,4-dimethyltribenzo[b,e,h][1,4,7]triazacyclonona-2,5,8-triene [(C6H5)3(NH)(NCH3)2, L1] with Fe[N(SiMe3)2]2 yields the dimeric iron(II) complex bis(μ-1,4-dimethyltribenzo[b,e,h][1,4,7]triazacyclonona-2,5,8-trien-7-ido)bis[(μ-1,4-dimethyltribenzo[b,e,h][1,4,7]triazacyclonona-2,5,8-trien-7-ido)iron(II)], [Fe(C20H18N3)4] or Fe2(L1)4 (9). Dissolution of 9 in tetrahydrofuran (THF) results in solvation by two THF ligands and the formation of a simpler monoiron complex, namely bis(μ-1,4-dimethyltribenzo[b,e,h][1,4,7]triazacyclonona-2,5,8-trien-7-ido-κN 7)bis(tetrahydrofuran-κO)iron(II), [Fe(C20H18N3)2(C4H8O)2] or (L1)2Fe(THF)2 (10). The reaction is reversible and 10 reverts in vacuo to diiron complex 9. In the structures of both 9 and 10, the monoanionic triazacyclophane ligand L1− is observed in only the less-symmetric saddle conformation. No bowl-shaped crown conformers are observed in the solid state, thus preventing chelating κ3-coordination to the metal as had been proposed earlier based on density functional theory (DFT) calculations. Instead, the L1− ligands are bound in either a η2-chelating fashion through the amide and one amine donor (for one of the four ligands of 9), or solely through their amide N atoms in an even simpler monodentate η1-coordination mode. Density functional calculations on dimer 9 revealed nearly full cationic charges on each Fe atom and no bonding interaction between the two metal centers, consistent with the relatively long Fe...Fe distance of 2.912 (1) Å observed in the solid state.

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Apparent Alkyl Transfer and Phenazine Formation via an Aryne Intermediate

Cited by 11 publications

References 30 publications

Synthesis and in Silico Evaluation of Novel Compounds for PET-Based Investigations of the Norepinephrine Transporter

Synthesis and in Silico Evaluation of Novel Compounds for PET-Based Investigations of the Norepinephrine Transporter

Influence of the N–H functionality on activating O,N,N-titanium complexes and controlling polyethylene molecular weights and distributions

Iron(II) complexes of dimethyltriazacyclophane

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