- Nickel-catalysed direct alkylation of thiophenes via double C(sp3)-H/C(sp2)-H bond cleavage: The importance of KH2PO4
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A Ni-catalyzed oxidative C-H/C-H cross-dehydrogenative coupling (CDC) reaction was developed for constructing various highly functionalized alkyl (aryl)-substituted thiophenes. This method employs thiophenes and aliphatic (aromatic) amides that contain an 8-aminoquinoline as a removable directing group in the presence of a silver oxidant. The approach enables the facile one-step synthesis of substituted thiophenes with high functional group compatibility via double C-H bond cleavage without affecting C-Br and C-I bonds. DFT calculations verify the importance of KH2PO4 as an additive for promoting C-H bond cleavage and support the involvement of a Ni(iii) species in the reaction.
- Wang, Xie,Xie, Peipei,Qiu, Renhua,Zhu, Longzhi,Liu, Ting,Li, You,Iwasaki, Takanori,Au, Chak-Tong,Xu, Xinhua,Xia, Yuanzhi,Yin, Shuang-Feng,Kambe, Nobuaki
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supporting information
p. 8316 - 8319
(2017/07/26)
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- Nickel-Catalyzed Addition-Type Alkenylation of Unactivated, Aliphatic C-H Bonds with Alkynes: A Concise Route to Polysubstituted γ-Butyrolactones
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(Chemical Equation Presented). Through the nickel-catalyzed chelation-assisted C-H bond activation strategy, the addition-type alkenylation of unreactive β-C(sp3)-H bonds of aliphatic amides with internal alkynes is developed for the first time to produce γ,δ-unsaturated carboxylic amide derivatives. The resulting alkenylated products can further be transformed into polysubstituted γ-butyrolactones with pyridinium chlorochromate (PCC).
- Li, Mingliang,Yang, Yudong,Zhou, Danni,Wan, Danyang,You, Jingsong
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supporting information
p. 2546 - 2549
(2015/05/27)
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- CYCLOALKYL METHOXYBENZYL PHENYL PYRAN DERIVATIVES AS SODIUM DEPENDENT GLUCOSE CO TRANSPORTER (SGLT2) INHIBITORS
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The invention relates to the cycloalkyl methoxybenzyl phenyl pyran derivatives as Sodium dependent glucose co transporter (SGLT) inhibitors, particularly SGLT2 and method of treating diseases, conditions and/or disorders inhibited by SGLT2 with them, and processes for preparing them.
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- Chemoselective esterification and amidation of carboxylic acids with imidazole carbamates and ureas
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Imidazole carbamates and ureas were found to be chemoselective esterification and amidation reagents. A wide variety of carboxylic acids were converted to their ester or amide analogues by a simple synthetic procedure in high yields.
- Heller, Stephen T.,Sarpong, Richmond
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supporting information; experimental part
p. 4572 - 4575
(2010/12/25)
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- Practical and efficient method for amino acid derivatives containing β-quaternary center: application toward synthesis of hepatitis C virus NS3 serine protease inhibitors
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A practical and efficient route toward synthesis of amino acid derivatives containing β-quaternary center has been developed using diastereoselective Strecker reaction. The method was employed for preparation of >100 g of β-methylcyclohexyl glycine deriva
- Arasappan, Ashok,Venkatraman, Srikanth,Padilla, Angela I.,Wu, Wanli,Meng, Tao,Jin, Yan,Wong, Jesse,Prongay, Andrew,Girijavallabhan, Viyyoor,George Njoroge
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p. 6343 - 6347
(2008/02/10)
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- Design and synthesis of novel imidazoline derivatives with potent antihyperglycemic activity in a rat model of type 2 diabetes
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Imidazoline derivatives have been reported to show antihyperglycemic activity in vivo. In the present study, we first showed that there was no correlation between the in vivo antidiabetic activity and the in vitro affinities for the I1/I2
- Crane, Louis,Anastassiadou, Maria,Hage, Salome El,Stigliani, Jean Luc,Baziard-Mouysset, Genevieve,Payard, Marc,Leger, Jean Michel,Bizot-Espiard, Jean-Guy,Ktorza, Alain,Caignard, Daniel-Henri,Renard, Pierre
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p. 7419 - 7433
(2007/10/03)
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- NOVEL KETOAMIDES WITH CYCLIC P4'S AS INHIBITORS OF NS3 SERINE PROTEASE OF HEPATITIS C VIRUS
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The present invention discloses novel compounds which have HCV protease inhibitory activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such compounds as well as methods of using them to treat disorders associated with the HCV protease.
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Page/Page column 76
(2008/06/13)
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- NOVEL COMPOUNDS AS INHIBITORS OF HEPATITIS C VIRUS NS3 SERINE PROTEASE
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The present invention discloses novel compounds which have HCV protease inhibitory activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such compounds as well as methods of using them to treat disorders associated with the HCV protease.
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Page/Page column 88
(2008/06/13)
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- CYCLOBUTENEDIONE GROUPS-CONTAINING COMPOUNDS AS INHIBITORS OF HEPATITIS C VIRUS NS3 SERINE PROTEASE
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The present invention discloses novel compounds which have HCV protease inhibitory activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such compounds as well as methods of using them to treat disorders associated with the HCV protease.
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Page/Page column 77-78
(2010/02/14)
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- NOVEL COMPOUNDS AS INHIBITORS OF HEPATITIS C VIRUS NS3 SERINE PROTEASE
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The present invention discloses novel compounds which have HCV protease inhibitory activity as well as methods for preparing such compounds. In another embodiment, the invention discloses pharmaceutical compositions comprising such compounds as well as methods of using them to treat disorders associated with the HCV protease.
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Page/Page column 75
(2010/02/14)
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- Calcium Hypochlorite-Mediated Oxidation of Primary Alcohols to Methyl Esters
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Primary aliphatic alcohols can be converted to methyl esters using calcium hypochlorite as the oxidant.Primary benzyl alcohols can also be converted efficiently to methyl benzoates.
- McDonald, Chriss E.,Nice, Lois E.,Shaw, Anthony W.,Nestor, Nestor B.
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p. 2741 - 2744
(2007/10/02)
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- ACTIVATION AND SYNTHETIC APPLICATION OF THIOSTANNANES. PROTECTION OF CARBOXYL GROUPS WITH α-METHYLCINNAMYL ALCOHOL AS A MEANS OF CHEMODIFFERENTIATION AND SELECTIVE ACTIVATION
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α-Methylcinnamyl (MEC) esters are converted into parent carboxylic acids under mild conditions, various functions being tolerated including acetoxy, siloxy, MEM, and so on.Furthermore, MEC esters are transformed into other esters through CsF-promoted alkylation of intermediary organotin carboxylates.
- Sato, Tsueno,Otera, Junzo,Nozaki, Hitoshi
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p. 2959 - 2962
(2007/10/02)
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- Deuterium Isotope Effects for Migrating and Nonmigrating Groups in the Solvolysis of Neopentyl-Type Esters
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α- and γ-deuterium rate effects on the solvolysis of (1-methylcyclohexyl)methyl, (1-methylcyclopentyl)methyl, and (1-methylcyclobutyl)methyl sulfonate esters have been measured and the solvolysis products examined by 2H NMR spectroscopy.The results indicate that the products of the solvolysis of all these sulfonate esters are predominantely ((*) 98percent) rearranged.In the solvolysis of (1-methylcyclohexyl)methyl triflate, rearranged products with methyl migration slightly dominate over those with ring expansion.Normal isotope effects, 1.057 in 80E and 1.073 in 97T, are observed for the methyl-d3 compound and an inverse effect, 0,963, is observed in 80E for the methylene-d4 compound.However, in the solvolysis of both (1-methylcyclopentyl)methyl and (1-methylcyclobutyl)methyl sulfonates, the major products are those of ring expansion.In these examples, inverse effects are observed for the methyl-d3-labeled species.The observed isotope effects can be separated into respective values of 0.927, 0.913 for the nonmigrating methyl-d3 group and 1.177, 1.224 for the migrating methyl-d3 group in the solvolysis of (1-methylcyclohexyl)methyl triflate and (1-methylcyclopentyl)methyl brosylate.This explains the relative intramolecular migratory aptitudes of CH3/CD3 of 1.20 - 1.30 and the low γ-d9 isotope effect in the solvolysis of neopentyl sulfonates previously reported and makes them consistent with a mechanism which involves neighboring carbon participation during ionization.
- Shiner, V. J.,Tai, Jimmy J.
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p. 436 - 442
(2007/10/02)
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