- Copper-catalyzed domino reaction of carbodiimides and benzoic acid derivatives for the synthesis of quinazolinediones
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Quinazolinediones were obtained from 2-iodobenzoic acids and carbodiimide derivatives under mild reaction conditions via a copper-catalyzed domino reaction. The absence of an external base was essential to avoid the generation of amide by-products. Both alkyl- and aryl-substituted carbodiimides gave the corresponding quinazolinediones. However, the use of aryl-substituted carbodiimides resulted in low yields due to an undesired elimination process.
- Duangjan, Chanikan,Rukachaisirikul, Vatcharin,Saithong, Saowanit,Kaeobamrung, Juthanat
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p. 3537 - 3540
(2018/08/29)
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- Copper-Catalyzed C(sp3)-S Bond and C(sp2)-S Bond Cross-Coupling of 2-(2-Iodobenzoyl) Substituted or 2-(2-Iodobenzyl) Substituted 1,2,3,4-Tetrahydroisoquinolines with Potassium Sulfide: Synthesis of Isoquinoline-Fused 1,3-Benzothiazine Scaffolds
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The sulfuration reaction of 2-(2-iodobenzoyl) substituted, or 2-(2-iodobenzyl) substituted 1,2,3,4-tetrahydroisoquinolines with potassium sulfide proceeded in the presence of copper catalysts to give tetrahydroisoquinoline-fused 1,3-benzothiazine scaffolds in moderate to appropriate yields. This protocol provided an efficient and simple strategy to construct the corresponding benzothiazine derivatives via formation of C(sp3)-S bond and C(sp2)-S bond, which the C-S bonds formed via different routes in this reaction (traditional cross-coupling reaction via the cleavage of C-I bond and oxidative cross-coupling reaction via C(sp3)-H bond functionalization).
- Dang, Pan,Zheng, Zhilei,Liang, Yun
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p. 2263 - 2268
(2017/02/26)
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- Synthesis of 3-Hexyl-4-cyan-6,7-dimethoxy Isocoumarin
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4-(2-Amino-propanamideyl)-3,4,5,6,7,8,9,10-octahydro-5,6, 8-trihydroxy-3-methyl-isocoumarin, which was isolated from Flaveria bidentis (L) Kuntze, had herbicidal activity and its structure was modified in this research in order to get the isocoumarin comp
- Dong, Hai Jiao,Ban, Xu Dong,Li, Cheng,Huo, Jing Qian,Gong, Zhan Hu,Kang, Zhan Hai,Dong, Jin Gao,Zhang, Jin Lin
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p. 3623 - 3625
(2014/08/05)
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- Direct carbocyclizations of benzoic acids: Catalyst-controlled synthesis of cyclic ketones and the development of tandem aHH (acyl Heck-Heck) reactions
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The formation of exo-methylene indanones and indenones from simple ortho-allyl benzoic acid derivatives has been developed. Selective formation of the indanone or indenone products in these reactions is controlled by choice of ancillary ligand. This new process has a low environmental footprint as the products are formed in high yields using low catalyst loadings, while the only stoichiometric chemical waste generated from the reactants in the transformation is acetic acid. The conversion of the active cyclization catalyst into the Hermman-Beller palladacycle was exploited in a one-pot tandem acyl Heck-Heck (aHH) reaction, and utilized in the synthesis of donepezil. Carboxylic acids in aHH: Simple ortho-allyl benzoic acid derivatives have been utilized in an acyl Heck (aH) reaction to selectively form indanones and indenones. The conversion of the active cyclization catalyst into the Hermman-Beller palladacycle was exploited in a one-pot tandem acyl Heck-Heck (aHH) reaction to form two sp 2-sp2 bonds of (E)-trisubstituted olefins.
- Miles, Kelsey C.,Le, Chi,Stambuli, James P.
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supporting information
p. 11336 - 11339
(2014/10/16)
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- Palladium-catalyzed insertion of N-tosylhydrazones for the synthesis of isoindolines
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Isoindolines are synthesized by palladium-catalyzed coupling reaction of N-(2-iodobenzyl) anilines with α,β-unsaturated N-tosylhydrazones. The reaction has several potential advantages: (1) toleration of a wide range of functional groups, (2) easy to handle and with mild conditions, (3) enriches the isoindoline family, (4) two new bonds form in one step.
- Zhou, Ping-Xin,Luo, Jian-Yi,Zhao, Lian-Biao,Ye, Yu-Ying,Liang, Yong-Min
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supporting information
p. 3254 - 3256
(2013/05/08)
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- METHODS FOR TREATING HEMATOLOGICAL MALIGNANCIES
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The invention provides methods and pharmaceutical compositions for treating certain hematological cancers
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Page/Page column 57
(2012/02/13)
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- METHODS FOR TREATING GASTRIC AND PANCREATIC MALIGNANCIES
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The invention provides methods and pharmaceutical compositions for treating pancreatic cancer or gastric cancer or a metastasis thereof.
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Page/Page column 60-61
(2012/02/13)
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- FUSED RING ANALOGUES OF ANTI-FIBROTIC AGENTS
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The present invention relates to arylcarbonyl and heteroarylcarbonyl anthranilate compounds that may be useful as anti-fibrotic agents. The present invention also relates to methods for their preparation, pharmaceutical compositions containing these compounds and uses of these compounds in the treatment disorders.
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- Palladium-catalyzed tandem reaction to construct benzo[c]phenanthridine: Application to the total synthesis of benzo[c]phenanthridine alkaloids
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A concise and efficient synthesis of benzo[c]phenanthridines was accomplished by the palladium-catalyzed ring-opening coupling of azabicyclic alkene with o-iodobenzoates, followed by tandem cyclization. The strategy was successfully applied in the total synthesis of benzo[c]phenanthridine alkaloids such as sanguinarine, chelerythrine, nitidine and avicine.
- Lv, Pei,Huang, Kanglun,Xie, Longguan,Xu, Xiaohua
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supporting information; experimental part
p. 3133 - 3135
(2011/05/15)
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- A facile synthesis of dibenzopyrroloazepinones as tetracyclic allocolchicinoids - An unusual 1,2-phenyl shift
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A facile synthesis of dibenzopyrroloazepinones via an electrophilic cyclisation of a biphenyl-acyliminium ion is described; an unusual 1,2-phenyl shift occurs when the C-1′ carbon is the more nucleophilic than the C-2′ carbon.
- Wu, Liang,Aliev, Abil E.,Caddick, Stephen,Fitzmaurice, Richard J.,Tocher, Derek A.,King, Frank D.
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supporting information; experimental part
p. 318 - 320
(2010/05/01)
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- 2-iodoxybenzenesulfonic acid as an extremely active catalyst for the selective oxidation of alcohols to aldehydes, ketones, carboxylic acids, and enones with oxone
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Electron-donating group-substituted 2-iodoxybenzoic acids (IBXs) such as5-Me-IBX (1g), 5-MeO-IBX (1h), and 4,5-Me2-IBX were superior to IBX 1a as catalysts for the oxidation of alcohols with Oxone (a trad emark of DuPont) under nonaqueous conditions, although Oxone was almost insoluble in most organic solvents. The catalytic oxidation proceeded more rapidly and cleanly in nitromethane. Furthermore, 2-iodoxybenzenesulfonic acid (IBS, 6a) was much more active than modified IBXs. Thus, we established a highly efficient and selective method for the oxidation of primary and secondary alcohols to carbonyl compounds such as aldehydes, carboxylic acids, and ketones with Oxone in nonaqueous nitromethane, acetonitrile, or ethyl acetate in the presence of 0.05-5molpercentof 6a, which was generated in situ from 2-iodobenzenesulfonic acid (7a) or its sodium salt. Cycloalkanones could be further oxidized to α,β- cycloalkenones or lactones by controlling the amounts of Oxone under the same conditions as above. When Oxone was used under nonaqueous conditions, Oxone wastes could be removed by simple filtration. Based on theoretical calculations, we considered that the relatively ionic character of the intramolecular hypervalent iodine-OSO2 bond of IBS might lower the twisting barrier of the alkoxyperiodinane intermediate 16.
- Uyanik, Muhammet,Akakura, Matsujiro,Ishihara, Kazuaki
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supporting information; experimental part
p. 251 - 262
(2009/06/28)
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- Synthesis of isocoumarins via Pd/C-mediated reactions of o-iodobenzoic acid with terminal alkynes
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The coupling reaction of o-iodobenzoic acid with terminal alkynes by using a catalyst system of 10% Pd/C-Et3N-CuI-PPh3 has been studied in a variety of solvents. 3-Substituted isocoumarins were formed in good yields and with good reg
- Subramanian, Venkataraman,Batchu, Venkateswara Rao,Barange, Deepak,Pal, Manojit
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p. 4778 - 4783
(2007/10/03)
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- A new and practical PIFA-promoted olefin amidohydroxylation: Six- versus five-membered ring formation
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A novel access to the isoindolinone and isoquinolin-2-one skeletons from adequately substituted aromatic precursors is described. The key intramolecular cyclization step was performed by the action of phenyliodine(III)bis(trifluoroacetate) (PIFA) on the c
- Serna, Sonia,Tellitu, Imanol,Domínguez, Esther,Moreno, Isabel,SanMartín, Raúl
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p. 3483 - 3486
(2007/10/03)
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- Palladium-catalysed heteroannulation with terminal alkynes: A highly regio- and stereoselective synthesis of (Z)-3-aryl(alkyl)idene isoindolin-1- ones
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A highly regio- and stereoselective method for the synthesis of (Z)-3- aryl(alkyl)idene isoindolin-1-ones through palladium-copper catalysis is described. 2-Iodobenzamide 1 and its substituted derivatives 2-10 were reacted with terminal alkynes 11-19 in the presence of (PPh3)2PdCl2, CuI, and Et3N in DMF mostly at 80°C for 16 h to yield the 2-alkynyl substituted benzamides 20-38, 40-45, 77 which could then be cyclised with NaOEt in EtOH to the 3-aryl(alkyl)idene isoindolin-1-ones 46-49, 51, 53-55, 57, 59-71, 73 and 75. In certain cases, the isoindolin-1-ones 50, 52, 56 and 58 could be directly obtained by the palladium-catalysed reactions. (C) 2000 Elsevier Science Ltd.
- Kundu, Nitya G.,Khan, M. Wahab
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p. 4777 - 4792
(2007/10/03)
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- Concise synthesis of nitidine by palladium-assisted biaryl coupling reaction
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Formal total synthesis of nitidine (1) was accomplished via oxynitidine (7) by the internal aryl-aryl coupling reaction of iodo-amide (6) using palladium-assisted cyclization reaction.
- Harayama, Takashi,Shibaike, Kentaro
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p. 191 - 195
(2007/10/03)
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