- Novel transformation of aryl 2-iodophenyl ketones into 1,3-diarylisoquinolines with (TMS)2NH, styrenes, NIS, and tBuOK
-
Treatment of aryl 2-iodophenyl ketones with TMS2NH in the presence of Sc(OTf)3 at warming conditions, followed by the reaction with styrenes and NIS gave N-(1-aryl-2-iodoethyl) aryl 2-iodophenyl ketimines. Further treatment of N-(1-aryl-2-iodoethyl) aryl 2-iodophenyl ketimines with tBuOK in the presence of 1,10-phenanthroline at 120 °C generated 1,3-diarylisoquinolines in moderate yields through SET from tBuOK onto the iodophenyl group to form aryl radicals, their 6-endo-trig cyclization onto the vinyl groups, and aromatization of the cyclized intermediates. The present method is a novel approach for the preparation of the isoquinoline core via two steps from aryl 2-iodophenyl ketones.
- Shibasaki, Kaho,Togo, Hideo
-
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- A Serendipitous One-Pot Cyanation/Hydrolysis/Enamide Formation: Direct Access to 3-Methyleneisoindolin-1-ones
-
A direct, one-pot conversion of 2’-haloacetophenones to 3-methyleneisoindolin-1-one scaffolds using CuCN as the sole reagent without the need for moisture-free or anaerobic conditions is reported. This serendipitously discovered transformation with a broa
- Banik, Trisha,Kaliappan, Krishna P.
-
supporting information
p. 628 - 633
(2020/12/09)
-
- Fluorinations of unsymmetrical diaryliodonium salts containing: Ortho -sidearms; Influence of sidearm on selectivity
-
Activated aromatics were reacted with two different fluoroidoane reagents 1 and 2 in the presence of triflic acid to prepare only the para-substituted diaryliodonium salts. With fluoroiodane 1 the unsymmetrical diaryliodonium salts contained an ortho-propan-2-ol sidearm, whereas the alcohol sidearm was eliminated to form an ortho-styrene sidearm in the reaction with fluoroiodane 2. Only the diaryliodonium salts containing a styrene sidearm were fluorinated successfully to deliver para-fluorinated aromatics in good yields.
- Abudken, Ahmed M. H.,Hope, Eric G.,Singh, Kuldip,Stuart, Alison M.
-
supporting information
p. 6140 - 6146
(2020/10/30)
-
- 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
-
supporting information
p. 2438 - 2455
(2020/01/31)
-
- Visible Light Induced Cyclization to Spirobi[indene] Skeletons from Functionalized Alkylidienecyclopropanes
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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
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supporting information
(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
-
supporting information
p. 7396 - 7400
(2020/10/13)
-
- Highly Enantioselective Cobalt-Catalyzed Hydroboration of Diaryl Ketones
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A highly enantioselective cobalt-catalyzed hydroboration of diaryl ketones with pinacolborane was developed using chiral imidazole iminopyridine as a ligand to access chiral benzhydrols in good to excellent yields and ee. This protocol could be carried out in a gram scale under mild reaction conditions with good functional group tolerance. Chiral biologically active 3-substituted phthalide and (S)-neobenodine could be easily constructed through asymmetric hydroboration as a key step.
- Liu, Wenbo,Guo, Jun,Xing, Shipei,Lu, Zhan
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p. 2532 - 2536
(2020/04/02)
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- 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
-
supporting information
p. 9282 - 9296
(2019/08/12)
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- Palladium-Catalyzed Cascade Reductive and Carbonylative Cyclization of Ortho-Iodo-Tethered Methylenecyclopropanes (MCPs) Using N-Formylsaccharin as CO Source
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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
-
supporting information
p. 5677 - 5683
(2019/11/16)
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- Lewis or Br?nsted acid-catalysed reaction of propargylic alcohol-tethered alkylidenecyclopropanes with indoles and pyrroles for the preparation of polycyclic compounds tethered with indole or pyrrole motif
-
We developed a facile synthetic method to access cyclopenta[b]naphthalene derivatives via the Lewis or Br?nsted acid catalysed cascade nucleophilic addition, electronic cyclization, ring-opening rearrangement of propargylic alcohol-tethered alkylidenecyclopropanes with indole and pyrrole derivatives. The reaction exhibited a broad substrate scope and good functional group tolerance under metal-free conditions, affording the desired products in moderate to good yields.
- Wei, Hao-Zhao,Yu, Liu-Zhu,Shi, Min
-
supporting information
p. 135 - 139
(2019/12/26)
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- Enantioselective Synthesis of Indolines, Benzodihydrothiophenes, and Indanes by C?H Insertion of Donor/Donor Carbenes
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We employ a single catalyst/oxidant system to enable the asymmetric syntheses of indolines, benzodihydrothiophenes, and indanes by C?H insertion of donor/donor carbenes. This methodology enables the rapid construction of densely substituted five-membered rings that form the core of many drug targets and natural products. Furthermore, oxidation of hydrazones to the corresponding diazo compounds proceeds in situ, enabling a relatively facile one- or two-pot protocol in which isolation of potentially explosive diazo alkanes is avoided. Regioselectivity studies were performed to determine the impact of sterics and electronics in donor/donor metal carbene C?H insertions to form indolines. This methodology was applied to a variety of substrates in high yield, diastereomeric, and enantiomeric ratios and to the synthesis of a patented indane estrogen receptor agonist with anti-cancer activity.
- Souza, Lucas W.,Squitieri, Richard A.,Dimirjian, Christine A.,Hodur, Blanka M.,Nickerson, Leslie A.,Penrod, Corinne N.,Cordova, Jesus,Fettinger, James C.,Shaw, Jared T.
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supporting information
p. 15213 - 15216
(2018/10/31)
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- Cu(I)-Catalyzed Coupling and Cycloisomerization of Diazo Compounds with Terminal Yne-Alkylidenecyclopropanes: Synthesis of Functionalized Cyclopenta[ b]naphthalene Derivatives
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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
-
supporting information
p. 4516 - 4520
(2018/08/09)
-
- Visible-Light-Induced Decarboxylative Iodination of Aromatic Carboxylic Acids
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A convenient, efficient and practical visible-light-induced decarboxylative iodination of aromatic carboxylic acids has been developed, and the corresponding aryl iodides were obtained in good yields. The method shows some advantages including the use of readily available aromatic carboxylic acids as the starting materials, simple and mild conditions, high efficiency, wide substrate scope and tolerance of various functional groups.
- Jiang, Min,Yang, Haijun,Jin, Yunhe,Ou, Lunyu,Fu, Hua
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supporting information
p. 1572 - 1577
(2018/06/26)
-
- A one-pot radioiodination of aryl amines: Via stable diazonium salts: Preparation of 125I-imaging agents
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An operationally simple, one-pot, two-step tandem procedure that allows the incorporation of radioactive iodine into aryl amines via stable diazonium salts is described. The mild conditions are tolerant of various functional groups and substitution patterns, allowing late-stage, rapid access to a wide range of 125I-labelled aryl compounds and SPECT radiotracers.
- Sloan, Nikki L.,Luthra, Sajinder K.,McRobbie, Graeme,Pimlott, Sally L.,Sutherland, Andrew
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supporting information
p. 11008 - 11011
(2017/10/13)
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- Late stage iodination of biologically active agents using a one-pot process from aryl amines
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A simple and effective one-pot tandem procedure that generates aryl iodides from readily available aryl amines via stable diazonium salts has been developed. The operationally simple procedure and mild conditions allow late-stage iodination of a wide range of aryl compounds bearing various functional groups and substitution patterns. A novel synthetic strategy involving the preparation of nitroaryl compounds followed by a chemoselective tin(ii) dichloride reduction and the use of the one-pot diazotisation-iodination transformation was also developed. The general applicability of this approach was demonstrated with the preparation of a number of medicinally important compounds including CNS1261, a SPECT imaging agent of the N-methyl-d-aspartate (NMDA) receptor and IBOX, a compound used to detect amyloid plaques in the brain.
- Sloan, Nikki L.,Luthra, Sajinder K.,McRobbie, Graeme,Pimlott, Sally L.,Sutherland, Andrew
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p. 54881 - 54891
(2017/12/12)
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- Palladium-Catalyzed Acylations: One-Pot Synthesis of Indenones
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An efficient, one-pot synthesis of substituted indenones was accomplished starting from simple o-iodoketones and aldehydes. [Pd]-catalyzed direct acylation of o-iodoketones with aldehydes was employed as the key step. Subsequent intramolecular aldol condensation afforded the indenones. Notably, a variety of indenones were achieved. Significantly, the natural product neolignan was accomplished in one pot.
- Suchand, Basuli,Satyanarayana, Gedu
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supporting information
p. 372 - 381
(2017/04/26)
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- Synthesis of N -Aryl and N -Heteroaryl γ-, δ-, and ?-Lactams Using Deprotometalation-Iodination and N -Arylation, and Properties Thereof
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Xanthone, thioxanthone, fluorenone, benzophenone, 2-benzoylpyridine, dibenzofuran, and dibenzothiophene were deprotonated using a base prepared in situ from MCl 2 ·TMEDA (M = Zn or Cd; TMEDA = N, N, N ′, N ′-tetramethylethylenediamine) and lithium 2,2,6,6-tetramethylpiperidide in a 1:3 ratio, as demonstrated by subsequent iodolysis. The different aryl halides were involved as partners in the N -arylation of pyrrolidin-2-one. In the presence of copper(I) iodide and tripotassium phosphate, and using dimethyl sulfoxide as solvent, the reactions could be performed in yields ranging from 40 to 70%. Most of the products were tested for their antimicrobial, antifungal, antioxidant, and cytotoxic (MCF-7) activity.
- Amara, Rim,Bentabed-Ababsa, Ghenia,Hedidi, Madani,Khoury, Joseph,Awad, Ha?an,Nassar, Ekhlass,Roisnel, Thierry,Dorcet, Vincent,Chevallier, Floris,Fajloun, Ziad,Mongin, Florence
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p. 4500 - 4516
(2017/09/26)
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- Copper-catalyzed cascade cyclization of 1,5-enynes: Via consecutive trifluoromethylazidation/diazidation and click reaction: Self-assembly of triazole fused isoindolines
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Copper-catalyzed cascade cyclization of 1,5-enynes with two types of hypervalent reagents was developed via consecutive trifluoromethylazidation/diazidation and intramolecular click reaction (CUAAC), providing one-pot self-assembly of triazole fused isoindolines bearing a trifluoromethyl or an azide moiety. Moreover, the construction of a trifluoromethylcyclopropyl unit, which has been considered as a metabolically stable replacement for a tert-butyl moiety and was difficult to access, was also achieved under trifluoromethylazidation conditions. All these reactions exhibited excellent chemoselectivity, good to excellent yields and broad functional group tolerance.
- Yu, Liu-Zhu,Wei, Yin,Shi, Min
-
supporting information
p. 13163 - 13166
(2016/11/09)
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- Metal-free Mizoroki-Heck type reaction: A radical oxidative coupling reaction of 2-chloro-dithiane with substituted olefins
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An efficient metal-free Mizoroki-Heck type reaction of di- and tri-substituted alkenes with 2-chloro-dithiane has been developed under ambient pressure of air or using a relatively low loading of BF3·Et2O. This study represents a new environmentally friendly method for the syntheses of dithianyl-substituted alkene derivatives via a radical oxidative coupling process.
- Du, Wenbin,Lai, Junshan,Tian, Lixia,Xie, Xingang,She, Xuegong,Tang, Shouchu
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supporting information
p. 14017 - 14020
(2015/01/16)
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- Microwave-assisted facile and rapid friedel-crafts benzoylation of arenes catalyzed by bismuth trifluoromethanesulfonate
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The catalytic activity of metal triflates was investigated in Friedel-Crafts benzoylation under microwave irradiation. Friedel-Crafts benzoylation with benzoyl chloride of a variety of arenes containing electron-rich and electron-poor rings using bismuth triflate under microwave irradiation is described. This method allows the preparation of aryl ketones under solventless conditions in good to excellent yields and short reaction time. Bismuth triflate was easily recovered and reused five times without significant loss of the catalytic activity.
- Tran, Phuong Hoang,Hansen, Poul Erik,Pham, Thuy Thanh,Huynh, Vy Thanh,Huynh, Vy Hieu,Thi Tran, Thao Du,Huynh, Thanh Van,Le, Thach Ngoc
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p. 2921 - 2929
(2014/10/15)
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- Synthesis of structurally diverse diarylketones through the diarylmethyl sp3 C-H oxidation
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Under open-flask conditions, an efficient method to assemble a series of diversely functionalized diarylketones in the presence of commercially available NBS has been developed. Yields of up to 99% have been achieved employing diarylmethanes as starting material. Based on 18O-labeled experiment, the addition of stoichiometric water eventually leads to excellent yields in all carbonylation cases.
- He, Chao,Zhang, Xiaohui,Huang, Ruofeng,Pan, Jing,Li, Jiaqiang,Ling, Xuege,Xiong, Yan,Zhu, Xiangming
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p. 4458 - 4462
(2014/08/05)
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- Efficient and fast method for the preparation of Diaryl Ketones at room temperature
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Palladium-catalyzed cross-coupling reaction of arylboronic acids with acid chlorides at room temperature under phosphine-free conditions affords the corresponding aromatic ketones in excellent yields within short times. This synthetic method overcomes common disadvantages of Friedel-Crafts acylation procedures and is compatible with both electron-donating and electron-withdrawing substituents on the aryl ring of the acyl chlorides. Georg Thieme Verlag Stuttgart New York.
- Hajipour, Abdol Reza,Pourkaveh, Raheleh
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p. 1101 - 1105
(2014/05/20)
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- The first formation of (1Z)-1-alkylidene-1H-isobenzofuranium amides and 1H-inden-1-ones: Acid-promoted 5-exo cyclization and hydration/aldol condensation reactions of o-ethynylbenzophenones
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(1Z)-1-(2,2-Dimethylpropylidene)-1H-isobenzofuranium bis(trifluoromethylsulfonyl)amides were synthesized through 5-exo cyclization reactions between sterically encumbered o-alkynylbenzophenones and bis(trifluoromethylsulfonyl)imide (Tf2NH). It
- Nagahora, Noriyoshi,Wasano, Tatsuya,Nozaki, Kazuhiro,Ogawa, Tamaki,Nishijima, Shuhei,Motomatsu, Daiki,Shioji, Kosei,Okuma, Kentaro
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supporting information
p. 1423 - 1430
(2014/03/21)
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- The First Formation of (1Z)-1-Alkylidene-1H-isobenzofuranium Amides and 1H-Inden-1-ones: Acid-Promoted 5-exo Cyclization and Hydration/Aldol Condensation Reactions of o-Ethynylbenzophenones
-
(1Z)-1-(2,2-Dimethylpropylidene)-1H-isobenzofuranium bis(trifluoromethylsulfonyl)amides were synthesized through 5-exo cyclization reactions between sterically encumbered o-alkynylbenzophenones and bis(trifluoromethylsulfonyl)imide (Tf2NH). It
- Nagahora, Noriyoshi,Wasano, Tatsuya,Nozaki, Kazuhiro,Ogawa, Tamaki,Nishijima, Shuhei,Motomatsu, Daiki,Shioji, Kosei,Okuma, Kentaro
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supporting information
p. 1423 - 1430
(2015/10/05)
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- Cu(I)-catalyzed intramolecular cyclizations of substituted 2-iodobenzophenones under thermal and microwave conditions
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Novel, easy-to-perform and practical intramolecular Cu(I)-catalyzed cyclizations of substituted 2-iodobenzophenones under thermal and microwave conditions are reported. The isolated cyclized products under microwave conditions are obtained with high yields and with short reaction times offering a valuable and reliable alternative to other protocols for the synthesis of fluorene analogues.
- Haggam, Reda A.
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p. 6488 - 6494
(2013/07/26)
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- A simple, efficient, and recyclable phosphine-free catalytic system for carbonylative suzuki coupling reaction of aryl and heteroaryl iodides
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The carbonylative Suzuki cross-coupling reaction of arylboronic acid with aryl and heteroaryl iodides using polymer supported palladium-N-heterocyclic carbene complex (PS-Pd-NHC) as an efficient heterogeneous, recyclable catalyst is described. The developed catalytic system is found to be effective for the carbonylative coupling reaction of aryl, heteroaryl, and bicyclic heteroaryl iodides (5-iodoindole and 3-iodoquinoline) with various arylboronic acid derivatives providing good to excellent yields of the desired products. The protocol is advantageous due to the ease in handling of the catalyst and simple workup procedure, and environmentally benign with effective catalyst recyclability. Georg Thieme Verlag Stuttgart - New York.
- Qureshi, Ziyauddin S.,Deshmukh, Krishna M.,Tambade, Pawan J.,Bhanage, Bhalchandra M.
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experimental part
p. 243 - 250
(2011/03/18)
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- Deprotonative metalation of functionalized aromatics using mixed lithium-cadmium, lithium-indium, and lithium-zinc species
-
In situ mixtures of CdCl2TMEDA (0.5 equiv; TMEDA = N,N,N',N'-tetramethylethylenediamine) or InCl3 (0.33 equiv) with [Li(tmp)] (tmp = 2,2,6,6-tetramethylpiperidino; 1.5 or 1.3 equiv, respectively) were compared with the previously described mixture of ZnCl2-TMEDA (0.5 equiv) and [Li(tmp)] (1.5 equiv) for their ability to deprotonate anisole, benzothiazole, and pyrimidine. [(tmp)3CdLi] proved to be the best base when used in tetrahydrofuran at room temperature, as demonstrated by subsequent trapping with iodine. The Cd-Li base then proved suitable for the metalation of a large range of aromatics including benzenes bearing reactive functional groups (CONEt2, CO2Me, CN, COPh) or heavy halogens (Br, I), and heterocycles (from the furan, thiophene, pyrrole, oxazole, thiazole, pyridine, and diazine series). Fivemembered heterocycles benefiting from doubly activated positions were similarly dideprotonated at room temperature. The aromatic lithium cadmates thus obtained were involved in palladium-catalyzed cross-coupling reactions or simply quenched with acid chlorides.
- Snegaroff, Katia,L'Helgoual'ch, Jean-Martial,Bentabed-Ababsa, Ghenia,Nguyen, Tan Tai,Chevallier, Floris,Yonehara, Mitsuhiro,Uchiyama, Masanobu,Derdour, Aicha,Mongin, Florence
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experimental part
p. 10280 - 10290
(2010/04/24)
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- Deprotonative cadmation of functionalized aromatics
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This communication describes the deproto-metalation of a large range of aromatics including heterocycles using a newly developed lithium-cadmium base; the reaction proceeds at room temperature with an excellent chemoselectivity and efficiency, and proved to be regioselective in most cases. The Royal Society of Chemistry.
- L'Helgoual'ch, Jean-Martial,Bentabed-Ababsa, Ghenia,Chevallier, Floris,Yonehara, Mitsuhiro,Uchiyama, Masanobu,Derdour, Aicha,Mongin, Florence
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supporting information; experimental part
p. 5375 - 5377
(2009/03/11)
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- Iron-catalyzed aryl-aryl cross-couplings with magnesium-derived copper reagents
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(Chemical Equation Presented) Well-matched couples: Functionalized aryl and heteroaryl copper species obtained from the corresponding magnesium derivatives undergo Fe-catalyzed cross-coupling reactions with aryl iodides that bear keto, ester, triflate, or nitrile groups (see scheme).
- Sapountzis, Ioannis,Lin, Wenwei,Kofink, Christiane C.,Despotopoulou, Christina,Knochel, Paul
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p. 1654 - 1657
(2007/10/03)
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- Compounds and methods for inhibiting mitotic progression
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This invention relates to compounds and methods for the treatment of cancer. In particular, the invention provides compounds that inhibit Aurora kinase, pharmaceutical compositions comprising the compounds, and methods of using the compounds for the treat
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Page/Page column 141
(2008/06/13)
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- Consecutive cross-coupling of o-phenylenedizinc compound with acyl and/or aryl halides in the presence of Pd(0)-tris(2,4,6- trimethoxyphenyl)phosphine
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Consecutive cross-coupling of an o-phenylenedizinc compound 1 with two different acyl or aryl halides or acyl and aryl halides was accomplished in one pot by the catalysis of Pd(0)-tris(2,4,6-trimethoxyphenyl)phosphine to yield a variety of functionalized unsymmetrical 1,2-disubstituted benzenes in good yields. (C) 2000 Elsevier Science Ltd.
- Saiga, Akihiro,Hossain, Kabir M.,Takagi, Kentaro
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p. 4629 - 4632
(2007/10/03)
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- Formation and synthetic use of oxygen-centred radicals with (diacetoxyiodo)arenes
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o-Alkyl- or o-aryl-benzenecarboxylic acids and alcohols containing an aromatic ring are treated with a (diacetoxyiodo)arene-iodine system to give the corresponding cyclized products such as phthalide, benzocoumarin and chromane derivatives in moderate to good yields via the corresponding oxygen-centred radicals. For the carboxylic acids, [bis(trifluoroacetoxy)iodo]benzene functions effectively, while (diacetoxyiodo)benzene is effective for the alcohols. Chromane and its derivatives are obtained as iodinated compounds by hypoiodite species derived from (diacetoxyiodo)benzene and iodine. Copyright 1997 by the Royal Society of Chemistry.
- Togo, Hideo,Muraki, Takahito,Hoshina, Yoichiro,Yamaguchi, Kentaro,Yokoyama, Masataka
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p. 787 - 793
(2007/10/03)
-
- INTRAMOLECULAR CYCLIZATION OF ENYNE CUMULENALS
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Enyne cumulenals have been shown to undergo a Bergman cyclization or an intramolecular cycloaddition depending on the nature of substituents on the yne carbon.A hydrogen substituted cumulenal is cleanly converted to a naphthalene product while
- Garcia, J. Gabriel,Ramos, Bethzaida,Pratt, Lawrence M.,Rodriguez, Augusto
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p. 7391 - 7394
(2007/10/02)
-
- Synthesis of novel tetrahydrobenzazepinones
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The synthesis of novel tetrahydrobenzazepinones 1, 2, and 3 is described, as well as an improved synthesis of 4. The palladium catalyzed arylation approach to 1, 2, and 4 allows facile entry to benzazepinones lacking electron donating substituents on the
- Busacca, Carl A.,Johnson, Robert E.
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p. 165 - 168
(2007/10/02)
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- Preparative syntheses of optically pure ortho-substituted benzhydrols by asymmetric reductions of the corresponding benzophenones
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Lithium aluminium hydride previously treated with 2.5 equivalents of (S)-(+) or (R)-(-)-2-(2-iso-indolinyl)butan-1-ol 3 (readily available reagents) reduced the five ortho-substituted benzophenones 4-6, 8 and 10 into the corresponding optically active benzhydrols with nearly 100% enantiomeric excesses. Other examples of asymmetric reductions of prochiral benzophenones are given.
- Brown,Leze,Touet
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p. 841 - 844
(2007/10/02)
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- N-oxides of 5-oxo-1-phenyl-2-benzazepines
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Compounds of the formula STR1 wherein X and Y are selected from the group consisting of hydrogen, halogen and trifluoromethyl, are disclosed. The compounds are useful as intermediates in the production of 2-benzazepines, compounds of pharmacological activ
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-
- 2-Benzazepines. 1. Synthesis of 2-Benzazepin-4-ones and -5-ones via 2-Acetylenic Benzophenones
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The preparation of 1-phenyl-2-benzazepin-4-ones and -5-ones is discussed.The palladium-catalyzed coupling of an iodobenzophenone to a monosubstituted acetylene assembles the necessary atoms required for the benzazepine ring.Transformation of the acetylene
- Trybulski, Eugene J.,Reeder, Earl,Blount, John F.,Walser, Armin,Fryer, R. Ian
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p. 2441 - 2447
(2007/10/02)
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- Intermediates in the production of 2-benzazepines
-
Compounds of the formula STR1 wherein X and Y are selected from the group consisting of hydrogen, halogen and trifluoromethyl, are disclosed. The compounds are useful as intermediates in the production of 2-benzazepines, compounds of pharmacological activ
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-
-
- Triazolobenzazepines and processes for their production
-
There is presented triazolobenzazepines of the formula STR1 wherein R1 is hydrogen or lower alkyl and X and Y are hydrogen or halogen and the pharmaceutically acceptable salts thereof. Also disclosed are novel processes and intermediates leadin
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