58101-60-3Relevant academic research and scientific papers
A FACILE SYNTHESIS OF (+/-)-SESBANINE VIA γ-ADDITION OF KETENE SILYL ACETAL WITH QUATERNIZED METHYL NICOTINATE
Wada, Makoto,Nishihara, Yoshihiro,Akiba, Kin-ya
, p. 3267 - 3270 (1985)
Total synthesis of (+/-)-sesbanine (1) was carried out using γ-addition of ketene silyl acetal of methyl 3-cyclopentenecarboxylate to quaternized methyl nicotinate.The resulting 1,4-dihydropyridine (7) was oxidized with DDQ to give 4-substituted nicotinate (2) and 2 was converted to alcohol (8) by stereoselective oxymercuration followed by treatment with ammonia to give 1.
Carbocyclic 3′-deoxyadenosine-based highly potent bisubstrate-analog inhibitor of basophilic protein kinases
Enkvist, Erki,Raidaru, Gerda,Vaasa, Angela,Pehk, T?nis,Lavogina, Darja,Uri, Asko
, p. 5336 - 5339 (2007)
Carbocyclic analogs of 3′-deoxyadenosine were synthesized as racemates and the resulting stereoisomers were separated by chromatography on a chiral column. The conjugation of obtained compounds with hexa-(d-arginine) via 6-aminohexanoic acid linker led to a highly potent inhibitor of several basophilic protein kinases with some selectivity towards cAMP-dependent protein kinase.
Hydroalkylation of Olefins to Form Quaternary Carbons
Green, Samantha A.,Huffman, Tucker R.,McCourt, Ruairí O.,Van Der Puyl, Vincent,Shenvi, Ryan A.
supporting information, (2019/05/22)
Metal-hydride hydrogen atom transfer (MHAT) functionalizes alkenes with predictable branched (Markovnikov) selectivity. The breadth of these transformations has been confined to π-radical traps; no sp3 electrophiles have been reported. Here we describe a Mn/Ni dual catalytic system that hydroalkylates unactivated olefins with unactivated alkyl halides, yielding aliphatic quaternary carbons.
Hydroalkylation of Olefins to Form Quaternary Carbons
Green, Samantha A.,Huffman, Tucker R.,McCourt, Ruairí O.,Van Der Puyl, Vincent,Shenvi, Ryan A.
supporting information, p. 7709 - 7714 (2019/05/22)
Metal-hydride hydrogen atom transfer (MHAT) functionalizes alkenes with predictable branched (Markovnikov) selectivity. The breadth of these transformations has been confined to π-radical traps; no sp3 electrophiles have been reported. Here we describe a Mn/Ni dual catalytic system that hydroalkylates unactivated olefins with unactivated alkyl halides, yielding aliphatic quaternary carbons.
3-(1H-PYRAZOL-4-YL)PYRIDINE ALLOSTERIC MODULATORS OF THE M4 MUSCARINIC ACETYLCHOLINE RECEPTOR
-
Page/Page column 35, (2019/01/16)
The present invention is directed to pyrazol-4-yl-pyridine compounds which are allosteric modulators of the M4 muscarinic acetylcholine receptor. The present invention is also directed to uses of the compounds described herein in the potential treatment or prevention of neurological and psychiatric disorders and diseases in which M4 muscarinic acetylcholine receptors are involved. The present invention is also directed to compositions comprising these compounds. The present invention is also directed to uses of these compositions in the potential prevention or treatment of such diseases in which M4 muscarinic acetylcholine receptors are involved.
Copper-Catalyzed Modular Amino Oxygenation of Alkenes: Access to Diverse 1,2-Amino Oxygen-Containing Skeletons
Hemric, Brett N.,Chen, Andy W.,Wang, Qiu
supporting information, p. 1468 - 1488 (2019/01/25)
Copper-catalyzed alkene amino oxygenation reactions using O-acylhydroxylamines have been achieved for a rapid and modular access to diverse 1,2-amino oxygen-containing molecules. This transformation is applicable to the use of alcohols, carbonyls, oximes, and thio-carboxylic acids as nucleophiles on both terminal and internal alkenes. Mild reaction conditions tolerate a wide range of functional groups, including ether, ester, amide, carbamate, and halide. The reaction protocol allows for starting with free amines as the precursor of O-benzoylhydroxylamines to eliminate their isolation and purification, contributing to broader synthetic utilities. Mechanistic investigations reveal the amino oxygenation reactions may involve distinct pathways, depending on different oxygen nucleophiles.
Desymmetrization of cyclic olefins via asymmetric Heck reaction and hydroarylation
Liu, Sijia,Zhou, Jianrong
supporting information, p. 11758 - 11760 (2013/12/04)
An asymmetric Heck reaction allows desymmetrization of substituted cyclic olefins in high dr and ee. A bisphosphine oxide is uniquely stereoselective for this purpose. Desymmetrization of bicyclic olefins via hydroarylation can also be realized in high ee.
A new robust and versatile tetradentate linker for amides to be cleaved under mild conditions by unusual complexation of the amide nitrogen to Cu ++
Kramer, Rolf A.,Broehmer, Manuel C.,Forkel, Nina V.,Bannwarth
experimental part, p. 4273 - 4283 (2011/02/25)
The concept of weakening amide bonds by the rather unusual forced complexation of nitrogen to Cu++ is not limited to tridentate ligands and was extended in this work to tetradentate ligands as well. The use of cyclic tetradentate ligands was to no avail, but an open-chain and more-flexible tetradentate ligand allowed mild cleavage by methanolysis after complexation. The principle was applied to the development of a new linker for solid-phase chemistry, which was proven to be extremely robust, yet allowed mild cleavage after activation by Cu ++ complexation. Its stability and versatility was demonstrated by the successful application to a whole plethora of different types of reactions. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009.
Forced complexation of nitrogen leading to a weakening of amide bonds: Application to a new linker for solid-phase chemistry
Broehmer, Manuel C.,Bannwarth, Willi
experimental part, p. 4412 - 4415 (2009/05/07)
Cu2+ complexation of a bispicolylamide entity leads to a weakening of the N-C-amide bond, which subsequently can be cleaved under very mild conditions by methanolysis. On the basis of this principle we developed a versatile and robust linker for solid-phase chemistry. The stability of the linker was demonstrated under acidic and basic conditions, and it was evaluated for its utility in peptide synthesis as well as for reductive amination, Pd-mediated C-C-coupling, and metathesis reactions. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
Heterocyclic cyclopentyl tetrahydroisoquinoline and tetrahydropyridopyridine modulators of chemokine receptor activity
-
Page/Page column 35, (2008/06/13)
The present invention is directed to compounds of the formula I: Wherein R1, R2, R3, R4, R5, R6, R7, R8, R9, X, n and the broken lines are as defined herein which are useful as modulators of chemokine receptor activity. In particular, these compounds are useful as modulators of the chemokine receptor CCR-2.
