60441-55-6Relevant academic research and scientific papers
Direct transformation of aryl 2-pyridyl esters to secondary benzylic alcohols by nickel relay catalysis
Wu, Xianqing,Li, Xiaobin,Huang, Wenyi,Wang, Yun,Xu, Hui,Cai, Liangzhen,Qu, Jingping,Chen, Yifeng
supporting information, p. 2453 - 2458 (2019/03/29)
A direct transformation of aryl esters to secondary benzylic alcohols via tandem Ni-catalyzed cross-coupling reactions of aromatic 2-pyridyl esters with alkyl zinc reagents and carbonyl group reduction by Ni-H species is achieved. Preliminary mechanistic studies reveal that the Ni-H species is generated in situ via β-hydride elimination of the Negishi reagents. The reaction is catalyzed by bench-stable nickel salts under mild conditions with wide functional group tolerance.
Preparation of Functionalized Diaryl- and Diheteroaryllanthanum Reagents by Fast Halogen–Lanthanum Exchange
Benischke, Andreas D.,Anthore-Dalion, Lucile,Berionni, Guillaume,Knochel, Paul
supporting information, p. 16390 - 16394 (2017/11/28)
Aryl and heteroaryl halides (X=Br, I) undergo a fast and convenient halogen–lanthanum exchange with nBu2LaMe, which leads to functionalized diaryl- and diheteroaryllanthanum derivatives. Subsequent trapping reactions with selected electrophiles, such as ketones, aldehydes, or amides, proceeded smoothly at ?50 °C in THF, affording polyfunctionalized alcohols and carbonyl derivatives. Kinetic competition experiments revealed a similar reactivity trend as for Br/Mg exchange, but 106-times higher rates, making it comparable to Br/Li exchange.
Sequential Birch reaction and asymmetric Ir-catalyzed hydrogenation as a route to chiral building blocks
Paptchikhine, Alexander,Itto, Kaori,Andersson, Pher G.
supporting information; experimental part, p. 3989 - 3991 (2011/06/09)
A range of 1,2,4-trisubstituted cyclohexadienes obtained from the Birch reaction were hydrogenated asymmetrically to produce synthetically valuable chiral compounds in high enantio- and diastereoselectivity. The Royal Society of Chemistry.
Activation of functional arylzincs prepared from aryl iodides and highly enantioselective addition to aldehydes
DeBerardinis, Albert M.,Turlington, Mark,Pu, Lin
supporting information; experimental part, p. 2709 - 2712 (2009/05/27)
(Chemical Equation Presented) An easily available chiral ligand (S)-1 is found to activate the nucleophilic reaction of the arylzincs prepared in situ from the reaction of aryl iodides with Et2Zn. Both high yields and high enantioselectivity (u
Inhibitors of protein isoprenyl transferases
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, (2008/06/13)
Compounds having the formula STR1or a pharmaceutically acceptable salt thereof wherein R 1 is (a) hydrogen, (b) loweralkyl, (c) alkenyl, (d) alkoxy, (e) thioalkoxy, (f) halo, (g) haloalkyl, (h) aryl-L 2 --, and (i) heterocyclic-L 2 --; R 2 is selected from STR2(b) --C(O)NH--CH(R 14)--C(O)OR 15, STR3(d) --C(O)NH--CH(R 14)--C(O)NHSO 2 R 16, (e) --C(O)NH--CH(R 14)-tetrazolyl, (f) --C(O)NH-heterocyclic, and (g) --C(O)NH--CH(R 14)--C(O)NR 17 R 18 ; R 3 is heterocyclic, aryl, substituted or unsubstituted cycloalkyl; R 4 is hydrogen, lower alkyl, haloalkyl, halogen, aryl, arylakyl, heterocyclic, or (heterocyclic)alkyl; L 1 is absent or is selected from (a) --L 4 --N(R 5)--L 5 --, (b) --L 4 --O--L 5 --, (c) --L 4 --S(O) n --L 5 -- (d) --L 4 --L 6 --C(W)--N(R 5)--L 5 --, (e) --L 4 --L 6 --S(O)m--N(R 5)--L 5 --, (f) --L 4 --N(R 5)--C(W)--L 7 --L 5 --, (g) --L 4 --N(R 5)--S(O) p --L 7 --L 5 --, (h) optionally substituted alkylene, (i) optionally substituted alkenylene, and (j) optionally substituted alkynylene are inhibitors of protein isoprenyl transferases. Also disclosed are protein isoprenyl transferase inhibiting compositions and a method of inhibiting protein isoprenyl transferases.
Synthesis of 6-amylsalicylic acid from 3-anisaldehyde: Conversion of phthalide to thiophthalide by aluminum halide-butanethiol
Nishikawa, Asuka,Hashimoto, Yuichi,Shirai, Ryuichi
, p. 7307 - 7308 (2007/10/03)
The Lewis acid-promoted reaction of 3-butyl-7-methoxyphthalide with butanethiol gave the thiophthalide, which was converted to 6-amylsalicylic acid by alkaline hydrolysis and successive desulfurization by Raney Ni.
Alkylation of Aldehyde (Arenesulfonyl)hydrazones with Trialkylboranes
Kabalka, George W.,Maddox, John T.,Bogas, Ekaterini,Kelley, Shane W.
, p. 3688 - 3695 (2007/10/03)
(Arenesulfonyl)hydrazone derivatives of aryl aldehydes are readily alkylated by trialkylboranes in the presence of base to generate new organoboranes that may be converted to the corresponding substituted alkanes or alcohols depending upon the reaction conditions chosen. Both tosyl- and trisylhydrazone derivatives can be utilized in the reaction, which tolerates a variety of functional groups, making it a versatile alternative to both the Grignard and Suzuki-coupling reactions.
A facile one-pot synthesis of alkylarylcarbinols from α,α-dichloroarylmethanes and trialkylboranes in the presence of magnesium or lithium
Li, Nan-Sheng,Yu, Su,Kabalka, George W.
, p. 101 - 105 (2007/10/03)
α-Chlorobenzylmagnesium chloride or α-chlorobenzyllithium generated from α,α-dichloroarylmethane and magnesium or lithium, reacts in situ with trialkylboranes in THF at room temperature to produce the corresponding alkylarylcarbinols in good yields after oxidation with sodium perborate.
Alkylation of α,α-dichloroarylmethane with trialkylboranes: Synthesis of alkylarylcarbinols
Kabalka,Kabalka, George W.,Li,Nan-Sheng, Li,Yu,Su, Yu
, p. 8545 - 8548 (2007/10/02)
The alkylation of α,α-dichloroarylmethane with trialkylboranes occurs readily in the presence of t-butyllithium at -78°C. The reaction affords the corresponding alkylarylcarbinols in good yields after oxidation with sodium perborate.
Potential Antiestrogens. Synthesis and Evaluation of Mammary Tumor Inhibiting Activity of 1,2-Dialkyl-1,2-bis(3'-hydroxyphenyl)ethanes
Hartmann, Rolf W.,Buchborn, Helga,Kranzfelder, Gerhard,Schoenenberger, Helmut,Bogden, Arthur
, p. 1192 - 1197 (2007/10/02)
The syntheses of the meso-1,2-dialkyl-1,2-bis(3'-hydroxyphenyl)ethanes and of d,l-3,4-bis(3'-hydroxyphenyl)hexane (21) are described.In vitro these compounds inhibited the estradiol receptor interaction competitively, exhibiting Ka values between 0.20*109 (20) and 0.11*106 M-1 (24).In vivo the meso compounds reduced the estrone-stimulated mouse uterine growth; the most effective compounds were 20, 22, and 23 (53, 50, and 45percent inhibition, respectively).Compounds 20 and 22-24 showed weak estrogenic activity in the mouse uterine weight test and in the vaginal cornification test.Compounds 19 (NSC-297169), 20 (NSC-297170), and 22 (NSC-297171) exhibited a dose-dependent growth inhibition on the MCF-7 human breast tumor cell line (10-6 to 10-9 M).These compounds also showed a marked dose-dependent inhibition on the DMBA-induced, hormone-dependent mammary carcinoma of the Sprague-Dawley rat corresponding to their association constants.
