4810-79-1Relevant academic research and scientific papers
Efficient Diastereoselective Three-Component Synthesis of Pipecolic Amides
van der Heijden, Gydo,van Schaik, Timo B.,Mouarrawis, Valentinos,de Wit, Martin J. M.,Velde, Christophe M. L. Vande,Ruijter, Eelco,Orru, Romano V. A.
supporting information, p. 5313 - 5325 (2019/06/10)
An efficient Ugi-type three-component reaction (U-3CR) for the synthesis of pipecolic amides is reported. The U-3CR between electronically diverse isocyanides, carboxylic acids and 4-substituted Δ1-piperideines proceeds in a highly diastereoselective fashion. The Δ1-piperideines are obtained by NCS-mediated oxidation of the corresponding 4-substituted piperidines, which in turn are generated by an efficient two-step procedure involving the alkylation of 4-picoline and subsequent catalytic hydrogenation of the pyridine ring. We demonstrate the utility of this U-3CR, in combination with the convertible isocyanide 2-bromo-6-isocyanopyridine, in the synthesis of the anticoagulant argatroban.
Photocatalyzed Site-Selective C(sp3)-H Functionalization of Alkylpyridines at Non-Benzylic Positions
Fukuyama, Takahide,Nishikawa, Tomohiro,Yamada, Keiichi,Ravelli, Davide,Fagnoni, Maurizio,Ryu, Ilhyong
supporting information, p. 6436 - 6439 (2017/12/08)
Tetrabutylammonium decatungstate (TBADT)-photocatalyzed C-H functionalization of alkylpyridines was investigated. Unlike alkylbenzene counterparts, alkylation of α-C-H bonds did not proceed for the reaction of 2- and 4-alkylpyridines and reluctantly proceeded for 3-alkylpyridines, which allow site-selective C(sp3)-H functionalization at nonbenzylic positions. The observed nonbenzylic site selectivities are rationalized by the polar inductive effects of pyridyl groups in the SH2 transition states. Consecutive γ-functionalization and α-bromofunctionalization were successfully carried out in selected cases.
Regioselective synthesis of 4-alkylpyridines from pyridine and aldehydes via dipole reversal process of 1,4-dihydropyridine phosphonate
Lee, Phil Ho,Lee, Kooyeon,Shim, Jun Hwan,Lee, Seong Guk,Kim, Sundae
, p. 777 - 784 (2007/10/03)
4-Alkylation of pyridine has been accomplished by the reaction of ylides, derivated from 1,4-dihydropyridine phosphonate via phosphonioalkoxycarbonylation of pyridine with aldehydes and subsequent elimination of diisopropyl phosphate followed by aromatization with potassium tert-butoxide.
Bis(trimethylsilyl)ketene acetals as C,O-dinucleophiles: One-pot formation of polycyclic γ- and δ-lactones from pyridines and pyrazines
Rudler, Henri,Denise, Bernard,Xu, Yiming,Parlier, Andree,Vaissermann, Jacqueline
, p. 3724 - 3744 (2007/10/03)
Bis(trimethylsilyl)ketene acetals react with pyridines, quinoline and isoquinoline in the presence of stoichiometric amounts of methyl chloroformate to give the corresponding dihydropyridine-, dihydroquinoline- and dihydroisoquinoline-substituted carboxylic acids in satisfactory yields. The regio- and diastereoselectivities of the addition reactions, together with the presence or absence of rotamers, have been established. The isolated acids react with peracids to give β-hydroxy-δ-lactones through an intramolecular reaction. Similar lactonizations could also be brought about directly from the azaaromatic compounds in one-pot reactions with silica gel, iodine or bromine. In these cases δ-lactones or β-halo-δ-lactones were produced. The behaviour of pyrazines in these transformations is peculiar, since methyl chloroformate on its own induces the formation, through interaction with both nitrogen atoms, of polycyclic γ-lactones, a reaction formally reminiscent of the double nucleophilic addition of the same ketene acetals to (arene)tricarbonylchromium complexes. Most of the new structures were assigned through X-ray crystal structure determinations. Wiley-VCH Verlag GmbH & Co. KGaA, 2005.
LINCOMYCIN DERIVATIVES POSSESSING ANTIBACTERIAL ACTIVITY
-
Page 121-122, (2010/02/06)
Novel lincomycin derivatives are disclosed. These lincomycin derivatives exhibit antibacterial activity. As the compounds of the subject invention exhibit potent activities against bacteria, including gram positive organisms, they are useful antimicrobial agents. Methods of synthesis and of use of the compounds are also disclosed.
Lincomycin derivatives possessing antibacterial activity
-
, (2008/06/13)
Novel lincomycin derivatives are disclosed. These lincomycin derivatives exhibit antibacterial activity. As the compounds of the subject invention exhibit potent activities against bacteria, including gram positive organisms, they are useful antimicrobial agents. Methods of synthesis and of use of the compounds are also disclosed.
AN IMPROVED SYNTHESIS OF 4-SUBSTITUTED PYRIDINES FROM NITRILES
Chelucci, Giorgio,Giacomelli, Giampaolo,Scano, Gianfranco
, p. 107 - 108 (2007/10/02)
4-substituted pyridines have been prepared by a four-step sequence in 23-27percent overall yield from nitriles.
