cas 2894-51-1, 2-Amino-4'-chlorobenzophenone

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THERAPEUTIC COMPOSITION OF CURE-PRO COMPOUNDS FOR TARGETED DEGRADATION OF BET DOMAIN PROTEINS, AND METHODS OF MAKING AND USAGE
The present application is directed to a therapeutic composition, comprising two precursor compounds (monomers) that are suitable for assembly via two or more reversible covalent bonds. The monomers are polyfunctionalized molecules comprising a bioorthogo
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(2022/02/15)

THERAPEUTIC CURE-PRO COMPOUNDS FOR TARGETED DEGRADATION OF BET DOMAIN PROTEINS, AND METHODS OF MAKING AND USING THEM
The present application is directed to a therapeutically useful compound, comprised of two monomers that are linked to each other through two or more reversible covalent bonds. Each monomer is a polyfunctionalized molecule comprising a bioorthogonal linker element and ligand or pharmacophore, wherein the linker and ligand/pharmacophore are covalently coupled to each other either directly or through an optional connector moiety.
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(2022/02/15)

One-Pot Synthesis of 2-Aminobenzophenones from 2-Alkynyl Arylazides Catalyzed by Pd and Cu Precursors
We describe a novel one-pot three-step reaction of 2-alkynyl arylazides through palladium-catalyzed formation of 3-hydroxy-3-phenylindolin-2-ones followed by hydrolysis of amide bonds and copper-catalyzed decarboxylation to give 2-aminobenzophenones. This synthetic method works well with various 2-alkynyl arylazides and affords the products in moderate to good yields under mild reaction conditions.
Fan, Hui,Xu, Shijie,Yang, Fan,Zhang, Xiaoxiang,Zhao, Xuechun
supporting information
p. 4555 - 4558
(2021/08/30)

Bicyclic Bridgehead Phosphoramidite-Based Hybrid Diphosphorus Ligands: Design, Synthesis, and Application in Catalytic Asymmetric Hydrogenation
A strategy for chiral ligand design has been developed that allows for incorporation of an achiral bicyclic bridgehead phosphoramidite to generate a class of hybrid diphosphorus ligands for high activity and asymmetric control. Using this concept, a series of chiral phosphine-phosphoramidite ligands bearing the sole chirality at the ligand backbone have been prepared and successfully employed in the Rh-catalyzed asymmetric hydrogenation of 2-vinylanilides for the synthesis of optically active anilines bearing an ortho-tertiary benzylic stereocenter.
Du, Hong-Quan,Hu, Xiang-Ping
supporting information
p. 7678 - 7682
(2021/10/12)

One-Pot Synthesis of Spirocyclopenta[ a]indene Derivatives via a Cascade Ring Expansion and Intramolecular Friedel-Crafts-Type Cyclization
A one-pot efficient synthetic approach for the rapid construction of spirocyclopenta[a]indene derivatives has been developed via an iodine-initiated cascade ring expansion and intramolecular Friedel-Crafts-type cyclization from propargyl alcohol-tethered alkylidenecyclobutanes under mild conditions with broad substrate scope. This cascade process can be elegantly conducted on a gram scale. A plausible reaction mechanism has been proposed on the basis of a series of deuterium labeling and control experiments.
Li, Quanzhe,Liu, Jiaxin,Wei, Yin,Shi, Min
p. 2438 - 2455
(2020/01/31)

Visible Light Induced Cyclization to Spirobi[indene] Skeletons from Functionalized Alkylidienecyclopropanes
In this paper, we revealed a metal-free and visible light photoinduced method for the rapid construction of spirobi[indene] skeletons, providing a simple and efficient way for easy access to spirobi[indene] scaffolds under mild conditions along with a broad substrate scope and good functional group tolerance.
Li, Quanzhe,Liu, Jiaxin,Shi, Min,Wei, Yin
(2020/03/26)

Rapid construction of cyclopenta[: B] naphthalene frameworks from propargylic alcohol tethered methylenecyclopropanes
We have developed a new synthetic methodology for the rapid construction of cyclopenta[b]naphthalene frameworks from the reaction of propargylic alcohol tethered methylenecyclopropanes with mesyl chloride in the presence of triethylamine through cascade cyclization. The reaction can be performed under mild conditions without the use of transition metals, affording the target products in moderate to good yields, and this cyclization reaction process can be scaled up to a gram-scale synthesis.
Wei, Hao-Zhao,Li, Quan-Zhe,Wei, Yin,Shi, Min
p. 7396 - 7400
(2020/10/13)

Deoxygenative Arylation of Carboxylic Acids by Aryl Migration
An unprecedented deoxygenative arylation of aromatic carboxylic acids has been achieved, allowing the construction of an enhanced library of unsymmetrical diaryl ketones. The synergistic photoredox catalysis and phosphoranyl radical chemistry allows for precise cleavage of a stronger C?O bond and formation of a weaker C?C bond by 1,5-aryl migration under mild reaction conditions. This new protocol is independent of substrate redox-potential, electronic, and substituent effects. It affords a general and promising access to 60 examples of synthetically versatile o-amino and o-hydroxy diaryl ketones under redox-neutral conditions. Furthermore, it also brings one concise route to the total synthesis of quinolone alkaloid, (±)-yaequinolone A2, and a viridicatin derivative in satisfying yields.
Ruzi, Rehanguli,Ma, Junyang,Yuan, Xiang-Ai,Wang, Wenliang,Wang, Shanshan,Zhang, Muliang,Dai, Jie,Xie, Jin,Zhu, Chengjian
supporting information
p. 12724 - 12729
(2019/11/05)

Iron-Promoted Construction of Indoles via Intramolecular Oxidative C-N Coupling of 2-Alkenylanilines Using Persulfate
Indole scaffold synthesis relies primarily on oxidative C-H amination of N-protected alkenylanilines for C-N intramolecular cyclization reactions. Herein, for the first time, without N-protection, various readily prepared 2-alkenylanilines were transformed into the desired indole products in good yields by using K 2 S 2 O 8 as oxidant in the presence of catalytic amounts of FeF 2. The K 2 S 2 O 8 /FeF 2 system offers a direct and benign synthetic route to 3-arylindoles and it is applicable to a wide range of substituted indoles including drug intermediates.
Li, Yudong,Li, Yuehui,Luo, Shuping,Wang, Menglan,Wu, Qing-An
supporting information
p. 3085 - 3090
(2019/08/07)

Synthesis of Diiodinated All-Carbon 3,3′-Diphenyl-1,1′-spirobiindene Derivatives via Cascade Enyne Cyclization and Electrophilic Aromatic Substitution
A synthetic method for the construction of diiodinated all-carbon spirobiindene derivatives has been developed from the reaction of propargyl alcohol-tethered alkylidenecyclopropanes with iodine. The reaction proceeded through an iodination-initiated cascade intramolecular enyne cyclization and electrophilic aromatic substitution reaction process in 1,2-dichloroethane upon heating, giving desired spirocyclic products in moderate to excellent yields. Further transformation of the obtained products has also been presented.
Li, Quanzhe,Yu, Liuzhu,Wei, Yin,Shi, Min
p. 9282 - 9296
(2019/08/12)

Palladium-Catalyzed Cascade Reductive and Carbonylative Cyclization of Ortho-Iodo-Tethered Methylenecyclopropanes (MCPs) Using N-Formylsaccharin as CO Source
A palladium-catalyzed reductive and carbonylative cyclization of ortho-iodo-tethered methylenecyclopropanes (MCPs) using N-formylsaccharin as CO source has been developed, affording the desired indanone derivatives in moderate to good yields with high regio- and stereoselectivity and good functional group compatibility.
Fan, Xing,Shi, Min,Wei, Yin
p. 5677 - 5683
(2019/11/16)

GLUN2C/D SUBUNIT SELECTIVE ANTAGONISTS OF THE N-METHYL-D-ASPARTATE RECEPTOR
A compound according to Formula (I) or salts or prodrugs thereof and pharmaceutical formulations comprising the compound are provided herein for the treatment of neurological disorders. The disorders may include providing neuroprotection, preventing neurodegeneration, treating neuropathic pain or treating schizophrenia, psychoses or depression. Furthermore, the compounds may be used in combination with another active ingredient.
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(2019/10/23)

Enantioselective Intramolecular Copper-Catalyzed Borylacylation
An enantioselective copper-catalyzed intramolecular borylacylation is reported. The reaction proceeds through an initial enantioselective borylcupration of the styrene, followed by a nucleophilic attack on the tethered carbamoyl chloride. The products, chiral borylated 3,3-disubstituted oxindoles, were generated in excellent yields and enantioselectivities. The versatile carbon–boron bond provides a platform for a wide array of diversification.
Whyte, Andrew,Burton, Katherine I.,Zhang, Jingli,Lautens, Mark
supporting information
p. 13927 - 13930
(2018/10/02)

Cu(I)-Catalyzed Coupling and Cycloisomerization of Diazo Compounds with Terminal Yne-Alkylidenecyclopropanes: Synthesis of Functionalized Cyclopenta[ b]naphthalene Derivatives
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 terminal alkyne in yne-tethered ACP and then undergoes a domino cycloisomerization of a 6π-electrocyclization and cyclopropane ring-opening rearrangement to give functionalized cyclopenta[b]naphthalene derivatives in moderate to excellent yields under mild conditions.
Li, Peng-Hua,Yu, Liu-Zhu,Zhang, Xiao-Yu,Shi, Min
p. 4516 - 4520
(2018/08/09)

Cascade Amination/Cyclization/Aromatization Process for the Rapid Construction of [2,3-c]Dihydrocarbazoles and [2,3-c]Carbazoles
An intramolecular cascade amination/cyclization/aromatization reaction of functionalized alkylidenecyclopropanes has been developed in the presence of silver acetate, affording a variety of [2,3-c]dihydrocarbazoles and [2,3-c]carbazoles in moderate to excellent yields. The mechanistic investigations revealed that this cascade reaction proceeds through a radical initiated process. Moreover, further transformations for the synthesis of eustifoline-D and an OLED exhibit a potential synthetic utility of this method.
Fan, Xing,Yu, Liu-Zhu,Wei, Yin,Shi, Min
p. 4476 - 4479
(2017/09/11)

Chemoselective double annulation of two different isocyanides: Rapid access to trifluoromethylated indole-fused heterocycles
An unprecedented chemoselective double annulation of α-trifluoromethylated isocyanides with o-acylaryl isocyanides has been developed. This new reaction provides a rapid, efficient, and complete atom-economic strategy for the synthesis of trifluoromethylated oxadiazino[3,2-α]indoles in a single operation from readily available starting materials. Isocyanide insertion into C=O double bonds is disclosed for the first time as indicated by the results of 18O-labeling experiment. A mechanism for this domino reaction is proposed involving chemoselective heterodimerization of two different isocyanides, followed by indole-2,3-epoxide formation and rearrangement.
Gao, Yuelei,Hu, Zhongyan,Dong, Jinhuan,Liu, Jun,Xu, Xianxiu
supporting information
p. 5292 - 5295
(2017/11/06)

2-Arylindoles: A new entry to transition metal-free synthesis of 2-aminobenzophenones
Various 2-aminobenzophenones were synthesized from readily available 2-arylindoles in DMSO under O2 balloon atmosphere. The synthesis was carried out without the aid of a transition metal catalyst or moisture-sensitive organometallic reagents from 2-arylindoles.
Yu, Jin,Moon, Hye Ran,Min, Beom Kyu,Kim, Jae Nyoung
supporting information
p. 893 - 897
(2016/06/14)

Synthesis of 3-Sulfonylamino Quinolines from 1-(2-Aminophenyl) Propargyl Alcohols through a Ag(I)-Catalyzed Hydroamination, (2 + 3) Cycloaddition, and an Unusual Strain-Driven Ring Expansion
We describe herein a silver-catalyzed conversion of 1-(2-aminophenyl)-propargyl alcohols to 4-substituted 3-tosylaminoquinolines using TsN3 as an amino surrogate. Controlled reactions reveal the pathway consisting of Ag(I)-catalyzed 5-exo-dig cyclization, catalyst-free (2 + 3) cycloaddition, and ring-expansive rearrangement via nitrogen expulsion. As a support study, we show that the cyclic enamines in similar conditions produce amidines via a C - C bond migration. (Chemical Equation Presented).
Kumar, Yalla Kiran,Kumar, Gadi Ranjith,Reddy, Thota Jagadeshwar,Sridhar, Balasubramanian,Reddy, Maddi Sridhar
supporting information
p. 2226 - 2229
(2015/05/13)

Palladium-catalyzed direct addition of arylboronic acids to 2-aminobenzonitrile derivatives: Synthesis, biological evaluation and in silico analysis of 2-aminobenzophenones, 7-benzoyl-2-oxoindolines, and 7-benzoylindoles
A palladium-catalyzed direct addition of arylboronic acids to unprotected 2-aminobenzonitriles has been developed, leading to a wide range of 2-aminobenzophenones with moderate to excellent yields. The transformation has broad scope and high functional group tolerance. Moreover, 2-oxoindoline-7-carbonitrile and indole-7-carbonitrile were applicable to this process for the construction of 7-benzoyl-2-oxoindolines and 7-benzoylindoles, respectively. Among the compounds examined, compound 4e possessed the most potent anticancer activity against H446 and HGC-27 in vitro, with IC50 values of 0.02 μmol L-1 and 0.09 μmol L-1, respectively, while compound 4a showed the best potent anticancer activity against SGC-7901 with an IC50 value of 0.01 μmol L-1. Furthermore, we also performed in silico molecular docking calculations to investigate the interaction mode and binding affinity between the examined compounds and their tubulin target. This journal is
Chen, Jiuxi,Ye, Leping,Su, Weike
supporting information
p. 8204 - 8211
(2015/01/08)

DIHYDROQUINAZOLINONE ANALOGUES
The present invention encompasses compounds of general formula (I) wherein the groups R1 to R4 and A1 to A5 have the meanings given in the claims and in the specification. The compounds of the invention are suitable for the treatment of diseases characterized by excessive or abnormal cell proliferation pharmaceutical preparations containing such compounds and their uses as a medicament.
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(2014/10/16)

DIHYDROQUINAZOLINONE ANALOGUES AS BRD4 INHIBITORS
The present invention encompasses compounds of general formula (I) wherein the groups R1 to R4 and A1 to A5 have the meanings given in the claims and in the specification. The compounds of the invention are suitable for the treatment of diseases characterized by excessive or abnormal cell proliferation pharmaceutical preparations containing such compounds and their uses as a medicament.
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(2014/10/15)

Stabilizing PdII on hollow magnetic mesoporous spheres: A highly active and recyclable catalyst for carbonylative cross-coupling and Suzuki coupling reactions
A hollow magnetic mesoporous silica sphere (HMMS) catalyst has been synthesized using polystyrene microspheres as a chemical template. The catalyst was characterized by TEM, XRD, XPS and vibrating sample magnetometry (VSM). The catalyst shows high activity for the carbonylative cross-coupling reaction of aryl iodides with arylboronic acids and Suzuki coupling reactions. The newly developed catalyst is easy to recover by magnetic separation from the liquid phase of the reaction and can be recycled. Importantly, the catalyst revealed high efficiency and high stability under the reaction conditions and during recycling stages.
Niu, Jianrui,Liu, Mengmeng,Wang, Peng,Long, Yu,Xie, Miao,Li, Rong,Ma, Jiantai
p. 1471 - 1476
(2014/05/06)

Preparation of recoverable Fe3O4@PANI-PdII core/shell catalysts for Suzuki carbonylative cross-coupling reactions
We report on the synthesis, characterization and catalytic performance of a palladium-based superparamagnetic catalyst of Fe3O 4@polyaniline core/shell microspheres (Fe3O 4@PANI-PdII). The material was characterized by TEM, FT-IR, vibrating sample magnetometry (VSM), XRD, and XPS. The catalyst showed high activity for the carbonylative cross-coupling reaction of aryl iodide with arylboronic acid. Moreover it could selectively reduce the formation of a direct-coupling product. The newly developed catalyst could be recovered from the liquid phase easily by magnetic separation and recycled 5 times without any significant loss of activity. the Partner Organisations 2014.
Zhu, Xiaohang,Niu, Jianrui,Zhang, Fengwei,Zhou, Jinghui,Li, Xinzhe,Ma, Jiantai
p. 4622 - 4627
(2014/10/15)

Preparation of recoverable Fe3O4/PPy-PdII catalysts for carbonylative cross-coupling reactions
The hierarchical porous Fe3O4/PPy-PdII catalyst has been synthesized using Fe3O4 microspheres both as chemical template and oxidant source under sonication. The catalyst characterized by TEM, XRD, FT-IR, XPS and vibrating sample magnetometry (VSM). The catalyst showed high reactivity for the carbonylative cross-coupling reaction of aryl iodides with arylboronic acids. This newly developed catalyst could be easily recovered and revealed high efficiency and high stability under the reaction conditions and during recycling stages.
Niu, Jianrui,Xie, Miao,Zhu, Xiaohang,Long, Yu,Wang, Peng,Li, Rong,Ma, Jiantai
p. 247 - 252
(2014/07/07)

Palladium-catalyzed direct addition of 2-Aminobenzonitriles to sodium arylsulfinates: Synthesis of o-Aminobenzophenones
The first example of the palladium-catalyzed synthesis of o-Aminobenzophenones in moderate to excellent yields via a direct addition of sodium arylsulfinates to unprotected 2-Aminobenzonitriles was reported. A plausible mechanism for the formation of o-Aminobenzophenones involving desulfination and addition reactions was proposed. The utility of this transformation was demonstrated by its compatibility with a wide range of functional groups. Thus, the method represents a convenient and practical strategy for synthesis of o-Aminobenzophenones.
Chen, Jiuxi,Li, Jianjun,Su, Weike
p. 6439 - 6449
(2014/06/10)

A one-pot process for palladium catalyzed direct C-H acylation of anilines in water using a removable ortho directing group
A new mild, practical method for the synthesis of aminobenzophenone derivatives through a three step one-pot reaction sequence involving acylation of anilines, palladium catalyzed cross-dehydrogenative coupling of the formed anilides and the hydrolytic cleavage is reported. The full reaction sequence was performed under aqueous conditions.
Szabo, Fruzsina,Simko, Daniel,Novak, Zoltan
p. 3883 - 3886
(2014/01/06)

Preparation of Recoverable Pd Catalysts for Carbonylative Cross-Coupling and Hydrogenation Reactions
We report on the synthesis, characterization and catalytic performance of new, supported PdII and Pd0 catalysts. The catalysts are characterized by TEM, XRD, FTIR, X-ray photoelectron spectroscopy, and vibrating sample magnetometry. The catalysts are found to be active in both forms, PdII and Pd0, for the carbonylative cross-coupling reaction of aryl iodides with arylboronic acids, and for the hydrogenation of aromatic nitro- and unsaturated compounds. The newly developed catalysts are prepared by a synthetic strategy that is similar to the one used for other supported catalysts but are easier to recover-they can be recycled by magnetic separation from liquid phase reactions-and can be used for at least 5 consecutive trials without any decrease in activity.
Niu, Jian-Rui,Huo, Xing,Zhang, Feng-Wei,Wang, Hai-Bo,Zhao, Ping,Hu, Wu-Quan,Ma, Jiantai,Li, Rong
p. 349 - 354
(2013/03/13)

Structure-activity relationships and pharmacophore model of a noncompetitive pyrazoline containing class of GluN2C/GluN2D selective antagonists
Here we describe the synthesis and structure-activity relationship for a class of pyrazoline-containing dihydroquinolone negative allosteric modulators of the NMDA receptor that show strong subunit selectivity for GluN2C- and GluN2D-containing receptors over GluN2A- and GluN2B-containing receptors. Several members of this class inhibit NMDA receptor responses in the nanomolar range and are more than 50-fold selective over GluN1/GluN2A and GluN1/GluN2B NMDA receptors, as well as AMPA, kainate, GABA, glycine, nicotinic, serotonin, and purinergic receptors. Analysis of the purified enantiomers of one of the more potent and selective compounds shows that the S-enantiomer is both more potent and more selective than the R-enantiomer. The S-enantiomer had an IC 50 of 0.17-0.22 μM at GluN2D- and GluN2C-containing receptors, respectively, and showed over 70-fold selectivity over other NMDA receptor subunits. The subunit selectivity of this class of compounds should be useful in defining the role of GluN2C- and GluN2D-containing receptors in specific brain circuits in both physiological and pathophysiological conditions.
Acker, Timothy M.,Khatri, Alpa,Vance, Katie M.,Slabber, Cathryn,Bacsa, John,Snyder, James P.,Traynelis, Stephen F.,Liotta, Dennis C.
p. 6434 - 6456
(2013/09/23)

5-Aryl-imidazo[2,1-c][1,4]benzodiazepine derivatives as tricyclic constrained analogues of diazepam and Ro5-4864. Synthesis and binding properties at peripheral and central benzodiazepine receptors
Four series of 5-aryl-imidazo[2,1-c][1,4]benzodiazepine derivatives 1a-f, 2a-f, 3a-f, and 4a-f were synthesized and tested for their affinity at both the peripheral and central benzodiazepine receptors. Among the four series, only N-10 and C-11 sites were changed, mainly [N(CH3)-CO], [N-CH], [NH-CO], [NH-CH2], and in each series the halogen site was varied at the positions C-7, C-2′, and C-4′. In particular, 10-methyl-benzodiazepinones 1a and 1b were designed as tricyclic constrained analogues of diazepam and Ro5-4864. All the tested compounds did not show significant binding activity at central benzodiazepine receptors, but relatively good PBzR binding affinities were found for 10-methyl-benzodiazepinone 1c and benzodiazepines 2b, c. Benzodiazepinones 3a-f were prepared by cyclization with 1,1′-carbonyldiimidazole of the corresponding 2-(aryl-imidazol-1-yl- methyl)-arylamines, obtained from the suitable (2-amino-aryl)-aryl-methanols with 1,1′-carbonyldiimidazole in different conditions. N-Alkylation of 3a-f to 1a-f was achieved using dimethylformamide-dimethylacetal. Reduction of 3a-f to 4a-f was accomplished with lithium aluminum hydride or borane and oxidation of 4a-f to 2a-f was performed with manganese (IV) oxide.
Rizzetto, Elisa,Castellano,Florio,Vadori,Stefancich
p. 505 - 510
(2007/10/03)

Sulfonyl-containing 2,3-diarylindole compounds, methods for making same, and methods of use thereof
The present invention relates to sulfonyl-containing 2,3-diarylindole, especially to new compounds of general Formula, to a preparation method for their preparation, to pharmaceutical compositions containing said compound, and to the medical use thereof in the treatment of diseases relating to the inhibition of cyclooxygenase-2 (COX-2).
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(2010/02/06)

Synthesis and biological evaluation of substituted 2-sulfonyl-phenyl-3-phenyl-indoles: A new series of selective COX-2 inhibitors
A new series of substituted 2-sulfonyphenyl-3-phenyl-indole derivatives were synthesized and evaluated for their ability to inhibit COX-2 and COX-1enzymes. Most of the compounds synthesized were found to be highly potent and selective inhibitors of COX-2. This work led to the discovery of 2-aminosulfonylphenyl-3-phenyl-indole 5a which possesses higher activity and selectivity for COX-2 than Celecoxib both in vitro and in vivo.
Hu, Wenhui,Guo, Zongru,Chu, Fengming,Bai, Aiping,Yi, Xiang,Cheng, Guifang,Li, Jing
p. 1153 - 1160
(2007/10/03)

Synthesis of a New Generation Reverse Transcriptase Inhibitor via the BCl3/GaCl3-induced Condensation of Anilines with Nitriles (Sugasawa Reaction)
The synthesis of 1 was achieved in high overall yield through a mechanism-based improvement of the preparation of o-acyl anilines.
Houpis, Ioannis N.,Molina, Audrey,Douglas, Alan W.,Xavier, Lyndon,Lynch, Joseph,et al.
p. 6811 - 6814
(2007/10/02)

Synthesis of novel, substituted 4H-imidazo[1,5-a][1,4]benzodiazepines
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Fryer,Gu,Wang
p. 1661 - 1669
(2007/10/02)

Synthesis of 2-Aminobenzophenones via Rapid Halogen-Lithium Exchange in the Presence of a 2-Amino-N-Methoxy-N-methylbenzamide
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Frye, Stephen V.,Johnson, Marty C.,Valvano, Nicole L.
p. 3750 - 3752
(2007/10/02)

Competition in Intramolecular Arylation of Triphenylmethanols
Six new unsymmetrically substituted derivatives of 2-aminotriphenylmethanol (1) have been synthesised.The direction of ring closure following diazotisation and loss of nitrogen is determined by the nature of the intermediates formed.Where aryl radical intermediates are formed, the selectivity parallels that found in intermolecular competition by phenyl radicals, whereas copper-catalysed decomposition of the diazonium ion leads to intermediates which seem, from their selectivity, to possess considerable cationic nature.The slower thermal decomposition of the diazonium ions unexpectedly shows very little selectivity, suggesting that electrostatic interactions predominate in determining a very short lifetime of the crucial intermediate.
Bolton, Roger,Mguni, Raphael S.,Williams, Gareth H.
p. 405 - 408
(2007/10/02)

Friedel-Crafts Acylation of Some Aromatic Compounds with 2-Isocyanatobenzoyl Chloride
Friedel-Crafts acylation of benzene, toluene, anisole and chlorobenzene with 2-isocyanatobenzoyl chloride (1) afford either 2-aminobenzophenones (2) or 4,4-diaryl-1,2-dihydro-3,1-benzoxazin-2(4H)-ones (3) as major products depending on reaction temperature and/or substrate reactivity.Other minor products isolated are 3-aryl-1,2,3,4-tetrahydroquinazoline-2,4-diones (4), 6,12-diaryldibenzodiazocines (6) and 2-aminophenyl-α,α-diarylmethanols (7).The formation of 2 and 3 has been shown to take place via a common intermediate complex to which the cyclic 4-aryl-3,1-benzoxazinonium ion structure (12) has been assigned on the basis of its rection with methanol and 2-aminobenzophenone.While the formation of 6 occurs through the intermediate complex (12), 4-aryliminoquinazolin-2-ones (5) are formed most probably from the 1-AlCl3 complex.
Misra, B. K.,Rao, Y. R.,Mahapatra, S. N.
p. 1132 - 1138
(2007/10/02)