- Sulfoximines Assisted Rh(III)-Catalyzed C-H Activation/Annulation Cascade to Synthesize Highly Fused Indeno-1,2-benzothiazines
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A facile access to highly fused tetracyclic indeno-1,2-benzothiazines has been established via a Rh(III)-catalyzed C-H bond activation and intramolecular annulation cascade between sulfoximides and all-carbon diazo indandiones. This strategy is characterized by the fact that the diazo coupling partners do not require preactivation, along with its high efficiency, broad substrate generality, and facile transformation. Particularly, the highly conjugated tetracyclic products demonstrate good optical properties and can easily enter cells to emit bright fluorescence for live cell imaging.
- Li, Jian,Li, Hui,Fang, Daqing,Liu, Lingjun,Han, Xu,Sun, Jina,Li, Chunpu,Zhou, Yu,Ye, Deju,Liu, Hong
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supporting information
p. 15217 - 15227
(2021/10/25)
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- Utilizing Vinylcyclopropane Reactivity: Palladium-Catalyzed Asymmetric [5+2] Dipolar Cycloadditions
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Vinylcyclopropanes (VCPs) are commonly used in transition-metal-catalyzed cycloadditions, and the utilization of their recently realized reactivities to construct new cyclic architectures is of great significance in modern synthetic chemistry. Herein, a p
- Lan, Yu,Li, Miao-Miao,Lu, Liang-Qiu,Qu, Bao-Le,Xiao, Wen-Jing,Xiao, Yu-Qing,Xiong, Qin
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supporting information
p. 17429 - 17434
(2020/08/14)
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- Rigidification of a macrocyclic tris-catecholate scaffold leads to electronic localisation of its mixed valent redox product
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The catecholate groups in [{Pt(L)}3(μ3-tctq)] (H6tctq = 2,3,6,7,10,11-hexahydroxy-4b,8b,12b,12d-tetramethyltribenzotriquinacene; L = a diphosphine chelate) undergo sequential oxidation to their semiquinonate forms by voltammetry, with ΔE1/2 = 160-170 mV. The monoradical [{Pt(dppb)}3(μ3-tctq)]+ is valence-localised, with no evidence for intervalence charge transfer in its near-IR spectrum. This contrasts with previously reported [{Pt(dppb)}3(μ3-ctc)]+ (H6ctc = cyclotricatechylene), based on the same macrocyclic tris-dioxolene scaffold, which exhibits partly delocalised (class II) mixed valency.
- Greatorex, Sam,Vincent, Kevin B.,Baldansuren, Amgalanbaatar,McInnes, Eric J. L.,Patmore, Nathan J.,Sproules, Stephen,Halcrow, Malcolm A.
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p. 2281 - 2284
(2019/02/27)
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- METHOD FOR PREPARING INDENOISOQUINOLINE DERIVATIVES
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A method for preparing indenoisoquinoline derivatives represented by the following formula (I) is disclosed, which comprises the following steps: (A) providing a first reactant represented by the following formula (II) and a second reactant represented by the following formula (III): wherein, R1, R3, A, X, Y, Z, m and n are defined in the specification; and (B) reacting the first reactant represented by the formula (II) and the second reactant represented by the formula (III) in a solvent and selectively adding R2NH2 therein, to obtain the indenoisoquinoline derivatives represented by the formula (I).
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- An Elusive Nonaromatic Goal behind the Centropolyindanes: Aufbau of Veratrolo-Annelated Centropolyquinanes and Ozonolytic Abbau
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This study presents a potential experimental approach to the still elusive topologically nonplanar (K5) parent hydrocarbon, centrohexaquinane (1), by a construction-dismantling (aufbau–abbau) strategy via electron-rich aromatic centropolyindanes. A series of veratrole-based centropolyindanes are synthesized and subjected to ozonolytic degradation. These include the 2,2′-spirobiindanes 30–32, fuso-diindane 33, triptindanes 34–36, tribenzotriquinacene 37, and tetramethoxycentrohexaindane 9. Spirane 30 and propellane 36 are characterized by X-ray structure analysis. Ozonolysis of 32 and 33 gives a keto ester (59) and a dimethyl muconate (60), respectively. Dimethoxytriptindane 34 gives a [3.3.3]propellane-cis,cis-muconate (61) in good yield, the stereochemistry of which is determined by X-ray structure analysis. Tetramethoxytriptindane 35 gives the [3.3.3]propellane-bis-muconate 62 along with a [3.3.3]propellane-dialdehyde-muconate (63). Hexamethoxytriptindane 36 furnishes three products of mainly intra-dimethoxy cleavage, with the [3.3.3]propellane-tris-muconate 64 as the major component. X-ray structure analysis of 64 reveals molecular C3 symmetry and all-cis,cis stereochemistry of the three muconate groups. Hexamethoxytribenzotriquinacene 37 gives the triquinacene-tris-muconate 68, albeit in very low yield. Ozonolysis of tetramethoxycentrohexaindane 9 affords the bis-muconate 10 in moderate yield, along with two further centrohexacyclic products of single-wing degradation.
- Harig, Marco,Neumann, Beate,Stammler, Hans-Georg,Kuck, Dietmar
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p. 1078 - 1095
(2017/07/25)
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- 2,3,6,7,10,11-Hexamethoxytribenzotriquinacene: Synthesis, solid-state structure, and functionalization of a rigid analogue of cyclotriveratrylene
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The syntheses of several tribenzotriquinacenes bearing six methoxy groups at the outer peripheral positions of the aromatic rings are reported. The centro-methyl derivative is accessible in surprisingly good yield through two-fold cyclodehydration in the
- Harig, Marco,Neumann, Beate,Stammler, Hans-Georg,Kuck, Dietmar
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p. 2381 - 2397
(2007/10/03)
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- New Intramolecular Five-Endo-Mode Cyclization of Allenyl Aryl Ketones
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A convenient preparation of allenyl aryl ketones was achieved by the Weinreb-modified Grignard reaction of N-methoxy-N-methylamides with propargylmagnesium bromide.On treatment with BF3*OEt2, the allenyl aryl ketones were converted to methylenebenzocyclopentenones via a new 5-endo-mode cyclization.
- Nagao, Yoshimitsu,Lee, Woo-Song,Kim, Kweon
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p. 389 - 392
(2007/10/02)
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- A convenient route to indane-1,3-diones and 3-hydroxyindan-1-ones
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The synthesis of alkoxyindane-1,3-diones is described in four steps starting from benzaldehydes via 3-amino and 3-hydroxyindan-1-ones. Key Words: indane-1,3-diones / 3-hydroxyindan-1-ones / diazotization / oxidation
- Dallemagne, P.,Pilo, J. C.,Rault, S.,Robba, M.
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p. 121 - 124
(2007/10/02)
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