99484-07-8Relevant academic research and scientific papers
Aza-Nazarov Cyclization Reactions via Anion Exchange Catalysis
Donmez, Selin E.,Soyda?, Emine,Aydln, G?k?en,?ahin, Onur,Bozkaya, Ugur,Türkmen, Yunus E.
supporting information, (2019/01/21)
A catalytic aza-Nazarov cyclization between 3,4-dihydroisoquinolines and α,β-unsaturated acyl chlorides has been developed to access α-methylene-γ-lactam products in good yields (up to 79%) as single diastereomers. The reactions proceed efficiently when AgOTf is used as an anion exchange catalyst with a 20 mol % loading at 80 °C. Computational studies were performed to investigate the reaction mechanism, and the findings support the role of the -TMS group in reducing the reaction barrier of the key cyclization step.
Aza-Nazarov Cyclization Reactions via Anion Exchange Catalysis
Donmez, Selin E.,Soyda?, Emine,Aydln, G?k?en,?ahin, Onur,Bozkaya, U?ur,Türkmen, Yunus E.
supporting information, p. 554 - 558 (2019/01/24)
A catalytic aza-Nazarov cyclization between 3,4-dihydroisoquinolines and α,β-unsaturated acyl chlorides has been developed to access α-methylene-?-lactam products in good yields (up to 79%) as single diastereomers. The reactions proceed efficiently when AgOTf is used as an anion exchange catalyst with a 20 mol % loading at 80 °C. Computational studies were performed to investigate the reaction mechanism, and the findings support the role of the ?TMS group in reducing the reaction barrier of the key cyclization step.
Methyl-triflate-mediated dearylmethylation of: N -(arylmethyl)carboxamides via the retro-Mannich reaction induced by electrophilic dearomatization/rearomatization in an aqueous medium at room temperature
Peng, Hui,Ma, Jinhui,Luo, Wenkun,Zhang, Guangwen,Yin, Biaolin
supporting information, p. 2252 - 2256 (2019/05/17)
We have developed a protocol for the dearylmethylation of N-(arylmethyl)carboxamides under metal-free conditions in an aqueous medium at room temperature. This protocol involves methyl triflate-mediated successive C-C and C-N bond cleavages (retro-Mannich reaction) induced by electrophilic dearomatization/rearomatization. The dearomatization/rearomatization strategy can be expected to inspire the development of novel transformations based on the C-C bond cleavage in an environmentally benign manner.
Simple Metal-Free Direct Reductive Amination Using Hydrosilatrane to Form Secondary and Tertiary Amines
Varjosaari, Sami E.,Skrypai, Vladislav,Suating, Paolo,Hurley, Joseph J. M.,Lio, Ashley M. De,Gilbert, Thomas M.,Adler, Marc J.
supporting information, p. 1872 - 1878 (2017/06/09)
This work describes the use of cheap, safe, and easy-to-handle hydrosilatrane as the reductant in direct reductive amination reactions. This efficient method enables a facile, metal-free access to secondary and tertiary amines from a wide range of aldehydes and ketones, with the synthesis of tertiary amines requiring no additives at all. This reaction demonstrates excellent functional group tolerance, chemoselectivity, and scalability. (Figure presented.).
Skeletal Diversity in Combinatorial Fashion: A New Format for the Castagnoli-Cushman Reaction
Lepikhina, Anastasia,Dar'In, Dmitry,Bakulina, Olga,Chupakhin, Evgeny,Krasavin, Mikhail
, p. 702 - 707 (2017/11/20)
A new format for the Castagnoli-Cushman reaction of structurally diverse dicarboxylic acids, amines, and aldehydes in the presence of acetic anhydride as dehydrating agent is described. The reaction is distinctly amenable to parallel format: the combinato
Direct aziridination of nitroalkenes affording N-alkyl-C-nitroaziridines and the subsequent Lewis acid mediated isomerization to β-nitroenamines
Hao, Feiyue,Asahara, Haruyasu,Nishiwaki, Nagatoshi
, p. 5442 - 5445 (2017/11/06)
A mild and highly diastereoselective one-pot synthesis of trans-N-alkyl-C-nitroaziridines was achieved by treatment of nitroalkenes with aliphatic amines and N-chlorosuccinimide. Treatment of the obtained aziridines with a Lewis acid resulted in a facile ring opening reaction, accompanied by rearrangement and isomerization into functionalized (Z)-β-nitroenamines.
Novel CRAC channel conditioning agent, and preparation method and applications thereof
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Paragraph 0449; 0450; 0451; 0452, (2016/10/08)
The invention provides a novel CRAC (calcium release-activated calcium) channel conditioning agent, and a preparation method and applications thereof, and more specifically, the invention provides a compound represented by formula I, and the groups are defined in the patent specification. The invention also provides the preparation method of the compound represented by formula I, and applications of the compound as a CRAC channel conditioning agent.
Steric and electronic effects in capsule-confined green fluorescent protein chromophores
Baldridge, Anthony,Samanta, Shampa R.,Jayaraj, Nithyanandhan,Ramamurthy,Tolbert, Laren M.
supporting information; scheme or table, p. 712 - 715 (2011/04/15)
The turn-on of emission in fluorescent protein chromophores sequestered in an "octaacid" capsule is controlled by stereoelectronic effects described by a linear free energy relationship. The stereochemical effects are governed by both the positions and volumes of the aryl substituents, while the electronic effects, including ortho effects, can be treated with Hammett σ parameters. The use of substituent volumes rather than A values reflects packing of the molecule within the confines of the capsule.
Efficient synthesis of new 4-arylideneimidazolin-5-ones related to the GFP chromophore by 2+3 cyclocondensation of arylideneimines with imidate ylides
Baldridge, Anthony,Kowalik, Janusz,Tolbert, Laren M.
scheme or table, p. 2424 - 2436 (2010/09/06)
A 2+3 condensation of a wide assortment of Schiff bases, prepared from aromatic aldehydes and primary amines, with methyl (1-ethoxyethylideneamino) acetate allows convenient access to an extensive family of substituted 4-arylideneimidazolin-5-one analogues of the green fluorescent protein (GFP) chromophore. Georg Thieme Verlag Stuttgart · New York.
Activation of fluorescent protein chromophores by encapsulation
Baldridge, Anthony,Samanta, Shampa R.,Jayaraj, Nithyanandhan,Ramamurthy,Tolbert, Laren M.
supporting information; experimental part, p. 1498 - 1499 (2010/04/03)
(Figure Presented) Chromophores related to fluorescent proteins, when sequestered into the "octaacid" capsule, recover their fluorescence. The fluorescence recovery is related to the inhibition of torsional motions within the cavity, implicating the single-bond torsion as an important contributor to internal conversion within this important class of chromophores.
