72316-17-7Relevant articles and documents
Rate dependence on inductive and resonance effects for the organocatalyzed enantioselective conjugate addition of alkenyl and alkynyl boronic acids to β-indolyl enones and β-pyrrolyl enones
Boylan, Amy,Li, Jian-Yuan,Lundy, Brian J.,May, Jeremy A.,Nguyen, Thien S.,Sundstrom, Sasha,Vallakati, Ravikrishna
, (2021/06/16)
Two key factors bear on reaction rates for the conjugate addition of alkenyl boronic acids to heteroaryl-appended enones: the proximity of inductively electron-withdrawing heteroatoms to the site of bond formation and the resonance contribution of available heteroatom lone pairs to stabilize the developing positive charge at the enone β-position. For the former, the closer the heteroatom is to the enone β-carbon, the faster the reaction. For the latter, greater resonance stabilization of the benzylic cationic charge accelerates the reaction. Thus, reaction rates are increased by the closer proximity of inductive electron-withdrawing elements, but if resonance effects are involved, then increased rates are observed with electron-donating ability. Evidence for these trends in isomeric substrates is presented, and the application of these insights has allowed for reaction conditions that provide improved reactivity with previously problematic substrates.
Mild Base Promoted Nucleophilic Substitution of Unactivated sp3-Carbon Electrophiles with Alkenylboronic Acids
Liu, Shiwen,Zeng, Xiaojun,Hammond, Gerald B.,Xu, Bo
supporting information, p. 3667 - 3671 (2018/09/12)
Diverse alkenylboronic acids react smoothly with various sp3-carbon electrophiles such as unactivated alkyl triflates in the presence of mild bases such as K3PO4. The reaction protocol is very mild and thereby enables high functional group tolerance. This transition metal-free condition is orthogonal towards the classic transition metal catalyzed Suzuki coupling. (Figure presented.).
ASYMMETRIC ADDITION REACTIONS
-
Paragraph 00140, (2016/12/26)
Processes of forming Csp2-Csp3 bonds at the allylic carbon of a cyclic allylic compound starting material are disclosed, in which a racemic mixture of a cyclic allylic compound having a leaving group attached to the allylic carbon is reacted with a compound having a nucleophilic carbon atom in the presence of a Rh(l), Pd(ll) or Cu(l) pre-catalyst and a chiral ligand. The reaction products containing the newly-formed Csp2-Csp3 bond are generated in high stereoisomeric excess, and may therefore serve as important organic building blocks in the preparation of new agrochemicals and pharmaceuticals.
N-B dative bond-induced [3.3.0] bicyclic boronate-tethered exo-selective intramolecular Diels-Alder reaction
Feng, Chao,Wang, Hong,Xu, Liang,Li, Pengfei
supporting information, p. 7136 - 7139 (2015/07/01)
We report herein a highly exo-selective intramolecular Diels-Alder reaction of alkenyl boronates which employs an N-B dative bond-involved bicyclic rigid tether. Complex C(sp3)-rich polycyclic molecules containing up to 8 stereocenters can be readily formed via an operationally simple two-step procedure.
Rhodium(III)-catalyzed cross-coupling of alkenylboronic acids and N -pivaloyloxylamides
Feng, Chao,Loh, Teck-Peng
supporting information, p. 3444 - 3447 (2014/07/21)
Rh(III)-catalyzed umpolung amidation of alkenylboronic acids for the synthesis of enamides is reported. This reaction proceeds readily at room temperature and displays an extremely wide spectrum of functional group tolerance. With cooperation of hydrobora
Anomalies in the stereoselectivity of the petasis reaction using styrenyl boronic acids
Churches, Quentin I.,Johnson, James K.,Fifer, Nathan L.,Hutton, Craig A.
scheme or table, p. 62 - 67 (2011/10/05)
The Petasis three-component coupling reaction of N-benzylphenylglycinol, glyoxylic acid, and styrenylboronic acids allows for the efficient synthesis of functionalized homoarylalanine derivatives. The reactions were shown to proceed in high yield but low selectivity, regardless of the nature of the substituent on the styrenylboronic acid component. Anomalies in the stereoselectivity of these reactions compared with previously reported results have been traced to the source of the organoboronic acid. Asymmetric dihydroxylation of the unsaturated amino acid derivatives enables a highly efficient route to dihydroxyhomoarylalanine derivatives. CSIRO 2011.
A general rhodium-catalyzed cyanation of aryl and alkenyl boronic acids
Anbarasan, Pazhamalai,Neumann, Helfried,Beller, Matthias
supporting information; scheme or table, p. 519 - 522 (2011/03/16)
Give me a cyanide: N-cyano-N-phenyl-p-methylbenzenesulfonamide as a cyanation reagent allows the synthesis of aryl(alkenyl) nitriles in good yield under mild conditions (see scheme; cod=cycloocta-1,5-diene). Combination of the procedure with the direct borylation of arenes and hydroboration of alkynes leads to the straightforward synthesis of various nitriles.
Synthesis and biological evaluation of 6,7-disubstituted 4-aminopyrido[2,3-d]pyrimidines as adenosine kinase inhibitors
Perner, Richard J.,Lee, Chih-Hung,Jiang, Meiqun,Gu, Yu-Gui,DiDomenico, Stanley,Bayburt, Erol K.,Alexander, Karen M.,Kohlhaas, Kathy L.,Jarvis, Michael F.,Kowaluk, Elizabeth L.,Bhagwat, Shripad S.
, p. 2803 - 2807 (2007/10/03)
The synthesis and structure-activity relationship of a series of 6,7-disubstituted 4-aminopyrido[2,3-d]pyrimidines as novel non-nucleoside adenosine kinase inhibitors is described. A variety of substituents, primarily aryl, at the C6 and C7 positions of the pyridopyrimidine core were found to yield analogues that are potent inhibitors of adenosine kinase. In contrast to the 5,7-disubstituted and 5,6,7-trisubstituted pyridopyrimidine series, these analogues exhibited only modest potency to inhibit AK in intact cells.
PREVENTIVES OR REMEDIES FOR MYOCARDITIS, DILATED CARDIOMYOPATHY AND CARDIAC INSUFFICIENCY CONTAINING NF-KAPPA B INHIBITORS AS THE ACTIVE INGREDIENT
-
, (2008/06/13)
The present invention provides a preventive or therapeutic agents for myocarditis, dilated cardiomyopathy and heart failure comprising NF-κB inhibitors as active ingredients.
Discovery of 4-amino-5-(3-bromophenyl)-7-(6-morpholino-pyridin-3-yl)pyrido [2,3-d]pyrimidine, an orally active, non-nucleoside adenosine kinase inhibitor
Lee,Jiang,Cowart,Gfesser,Perner,Ki Hwan Kim,Yu Gui Gu,Williams,Jarvis,Kowaluk,Stewart,Bhagwat
, p. 2133 - 2138 (2007/10/03)
Adenosine (ADO) is an endogenous homeostatic inhibitory neuromodulator that reduces cellular excitability at sites of tissue injury and inflammation. Inhibition of adenosine kinase (AK), the primary metabolic enzyme for ADO, selectively increases ADO concentrations at sites of tissue trauma and enhances the analgesic and antiinflammatory actions of ADO. Optimization of the high-throughput screening lead, 4-amino-7-aryl-substituted pteridine (5) (AK IC50 = 440 nM), led to the identification of compound 21 (4-amino-5-(3-bromophenyl)-7-(6-morpholino-pyridin-3-yl)pyrido [2,3-d]pyrimidine, ABT-702), a novel, potent (AK IC50 = 1.7 nM) nonnucleoside AK inhibitor with oral activity in animal models of pain and inflammation.
