Thermal decomposition of o-azidodiphenylmethane leading to 6H-azepino[1,2-a]-indole

Krbechek, L. O.; Takimoto, H. H.

doi:10.1021/jo01275a068

Cited by 21 publications

(6 citation statements)

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“…5-Hydroxy-4-octanone oxime (HB I ), a short-chain (C 8 ) analog of Lix63, was synthesized and purified according to procedures described elsewhere. [39][40][41] The final purified product was characterized by 1 H-NMR and FT-IR, and the results were consistent with those reported in the literature. 41 Nickel sulfate hexahydrate (98.5% purity), used to prepare nickel sulfate stock solution, was purchased from Sinopharm Chemical Reagent Co., Ltd. All other reagents were of analytical grades and used without further purification.…”

Section: Experimental Reagentssupporting

confidence: 82%

The Coordination Structure of the Extracted Nickel(II) Complex with a Synergistic Mixture Containing Lix63 and Versatic10

Zhu

et al. 2017

J Chinese Chemical Soc

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In the present work, the nickel(II) synergist complex with isobutyric acid (HLI ) and 5‐hydroxy‐4‐octanone oxime (HBI ), which were the corresponding short‐chain analogs of the active synergistic mixture of Versatic10 (HL) and Lix63 (5,8‐diethyl‐7‐hydroxy‐6‐dodecanoneoxime, HB), was prepared and studied by single‐crystal X‐ray diffraction (XRD). The crystal structure of the nickel(II) synergist complex showed that the composition of the complex was Ni(LI )2(HBI )2 with a cis‐form octahedron geometry structure. Both intra‐ and intermolecular hydrogen bonding were observed in the crystal lattice. Compared with the free ligands, similar band shifts of Fourier transform infrared (FT‐IR) spectra assigned to the stretching vibration of carbon–oxygen single bond (CO), the stretching vibration of carbon–nitrogen double bond (CN), and the disappearance of the scissoring vibration of α‐hydroxy (OH) were correspondingly found in both the nickel(II) synergist complex and the extracted nickel(II) complex in the nonpolar organic phase. Combined with the results from ESI‐MS, XRD, and slope analysis, it was concluded that the major species of the extracted nickel(II) complex in the nonpolar organic phase might possess a similar coordination structure [Ni(HB)2(L)2] as the nickel(II) synergist complex, along with the neutral complex [Ni(HB)(B)2].

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Section: Experimental Reagentssupporting

confidence: 82%

The Coordination Structure of the Extracted Nickel(II) Complex with a Synergistic Mixture Containing Lix63 and Versatic10

Zhu

et al. 2017

J Chinese Chemical Soc

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“…(1) The Efect of Metal Catalysts.--The dramatic role of a trace of iron powder encouraged us to look closer at this catalytic effect. A variety of transition metals, metal salts, metal complexes, co-ordinatively unsaturated metal complexes, zero-valent metal carbonyls, and Lewis acids, were investigated in the conversion of anthranil (10) into the acridones (1 1) and (12), no attempt being made to analyse the acridone ratio (see Table 2). Several very interesting points emerge: (a) all the catalysts had some beneficial effect on the conversion of the anthranil into products.…”

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“…(b) In almost all cases the acridone formation was accompanied by reductive ring-cleavage of the anthranil (10) to the 2-aminobenzophenone (13). While, in general, the amine was the minor product, in certain cases it was the major [copper (expt.…”

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“…Figure.The products (%) from heating 3-(p-tolyl)anthranii(10) under reflux in trichlorobenzene for 4 h with metal acetylacetonates 0 = acridone, Cl = amine, A = anthranil…”

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“…Reagents: i, heat. The effects of varying the reaction conditions are shown in Table1of 3-(p-tolyl)anthranil(10) under different conditions (see Scheme 4) 0 * TCB = 1,2,4-trichlorobenzene.X=N,Y=CH,…”

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An in-depth study of the azidobenzophenone–anthranil–acridone transformation

Hawkins¹,

Meth‐Cohn²

1983

J. Chem. Soc., Perkin Trans. 1

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The title transformation, particularly the conversion of anthranils into acridones, is shown to be critically sensitive to temperature, solvent, substituent, and metal catalysts. Thus the conversion of 3-(p-tolyl) anthranil into an acridone gives a ratio of 2and 3-methyl derivatives varying from 0.6 : 1 to 4.7 : 1 with changing temperature and solvent. In other similar thermolyses, solvents (e.g. 1,2,4-trichlorobenzene) were incorporated into the product and traces of metals and their derivatives had a dramatic effect on the rate and course of the reaction. The most effective catalysts were iron powder and aluminium acetylacetonate. 3-(2,6-Disubstituted pheny1)anthranils gave acridones in which the substituents were either lost or rearranged onto N or C, the last cases involving sequential [I ,5] -sigmatropic shifts.3-Thienylanthranils gave related thienoquinolones on thermolysis ; again the reactions were very sensitive to catalysis. Blocked thienylanthranils also gave rearrangement products, but the non-aromatic intermediates could be isolated.5 "C and mixed m.p.s are only slightly depressed thus accounting for Bamberger's erroneous interpretation,

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Cyclization of Vinyl and Aryl Azides into Pyrroles, Indoles, Carbazoles, and Related Fused Pyrroles

Berkowitz

McCombie

2017

Organic Reactions

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This chapter reviews in detail those reactions that form of a new pyrrole ring from vinyl, aryl, and heteroaryl azides via formal C–H insertion processes under thermal, photochemical, and metal‐catalyzed conditions. These reactions proceed via the intermediacy of vinyl or aryl nitrenes (or their metallonitrene equivalents) and generate a wide variety of pyrroles, indoles, carbazoles, and related systems. Methods for the synthesis of the starting azides are summarized, and a comprehensive survey of the cyclization processes is provided.

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Thermal decomposition of o-azidodiphenylmethane leading to 6H-azepino[1,2-a]-indole

Cited by 21 publications

References 0 publications

The Coordination Structure of the Extracted Nickel(II) Complex with a Synergistic Mixture Containing Lix63 and Versatic10

The Coordination Structure of the Extracted Nickel(II) Complex with a Synergistic Mixture Containing Lix63 and Versatic10

An in-depth study of the azidobenzophenone–anthranil–acridone transformation

Cyclization of Vinyl and Aryl Azides into Pyrroles, Indoles, Carbazoles, and Related Fused Pyrroles

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