102078-75-1Relevant academic research and scientific papers
Synthesis of Benzoisoselenazolones via Rh(III)-Catalyzed Direct Annulative Selenation by Using Elemental Selenium
Xu-Xu, Qing-Feng,Nishii, Yuji,Uetake, Yuta,Sakurai, Hidehiro,Miura, Masahiro
supporting information, p. 17952 - 17959 (2021/11/16)
Isoselenazolone derivatives have attracted significant research interest because of their potent therapeutic activities and indispensable applications in organic synthesis. Efficient construction of functionalized isoselenazolone scaffolds is still challenging, and thus new synthetic approaches with improved operational simplicity have been of particular interest. In this manuscript, we introduce a rhodium-catalyzed direct selenium annulation by using stable and tractable elemental selenium. A series of benzamides as well as acrylamides were successfully coupled with selenium under mild reaction conditions, and the obtained isoselenazolones could be pivotal synthetic precursors for several organoselenium compounds. Based on the designed control experiments and X-ray absorption spectroscopy measurements, we propose an unprecedented selenation mechanism involving a highly electrophilic Se(IV) species as the reactive selenium donor. The reaction mechanism was further verified by a computational study.
NIS-mediated oxidative arene C(sp2)-H amidation toward 3,4-dihydro-2(1H)-quinolinone, phenanthridone, and N-fused spirolactam derivatives
Wu, Lingang,Hao, Yanan,Liu, Yuxiu,Wang, Qingmin
, p. 6762 - 6770 (2019/07/22)
A new radical-mediated intramolecular arene C(sp2)-H amidation of 3-phenylpropanamides or [1,1′-biphenyl]-2-carboxamides was developed to prepare a series of 3,4-dihydro-2(1H)-quinolinone and phenanthridone derivatives in moderate to excellent yields (33-94%). Spirolactams could also be obtained using this protocol.
Nickel-Catalyzed Denitrogenative ortho-Arylation of Benzotriazinones with Organic Boronic Acids: an Efficient Route to Losartan and Irbesartan Drug Molecules
Thorat, Vijaykumar H.,Upadhyay, Nitinkumar Satyadev,Cheng, Chien-Hong
supporting information, p. 4784 - 4789 (2018/11/10)
Denitrogenative ortho-arylation, vinylation and methylation of 1,2,3-benzotriazin-4-(3H)-ones with organic boronic acids catalyzed by nickel complexes to give a wide range of o-substituted benzamides were demonstrated. Further, the catalytic reaction is successfully applied to the synthesis of the popular hypertensive drugs losartan and irbesartan in high yields. (Figure presented.).
3D-QSAR and 3D-QSSR models of negative allosteric modulators facilitate the design of a novel selective antagonist of human α4β2 neuronal nicotinic acetylcholine receptors
Henderson, Brandon J.,Orac, Crina M.,MacIagiewicz, Iwona,Bergmeier, Stephen C.,McKay, Dennis B.
scheme or table, p. 1797 - 1813 (2012/04/10)
Subtype selective molecules for α4β2 neuronal nicotinic acetylcholine receptors (nAChRs) have been sought as novel therapeutics for nicotine cessation. α4β2 nAChRs have been shown to be involved in mediating the addictive properties of nicotine while other subtypes (i.e., α3β4 and a7) are believed to mediate the undesired effects of potential CNS drugs. To obtain selective molecules, it is important to understand the physiochemical features of ligands that affect selectivity and potency on nAChR subtypes. Here we present novel QSAR/QSSR models for negative allosteric modulators of human α4β2 nAChRs and human α3β4 nAChRs. These models support previous homology model and site-directed mutagenesis studies that suggest a novel mechanism of antagonism. Additionally, information from the models presented in this work was used to synthesize novel molecules; which subsequently led to the discovery of a new selective antagonist of human α4β2 nAChRs.
A novel synthesis of imidazoles via the cycloaddition of nitrile ylides to their imidoyl chloride precursors
Groundwater, Paul W.,Garnett, Ian,Morton, Andrew J.,Sharif, Toqir,Coles, Simon J.,Hursthouse, Michael B.,Nyerges, Miklos,Anderson, Rosaleen J.,Bendell, David,McKillop, Alexander,Zhang, Weimin
, p. 2781 - 2787 (2007/10/03)
The synthesis of imidazoles via the cycloaddition of nitrile ylides to their imidoyl chloride precursors was presented. The nitrile ylides were prepared by the 1,3-dehydrochlorination of imidoyl chlorides. It was shown that the HOMO of the 'bent' nitrile ylide is heavily localized on the methane terminus and is compatible with protonation at this carbon in substituted nitrile ylides and with the regioisomers obtained in biomolecular nitrile ylide cycloadditions. The observed regiochemistry of the cycloaddition was rationalized by energy calculations on the frontier molecular orbitals of the reactants using semi-empirical methods.
REGIOSPECIFIC PALLADIUM CATALYSED TANDEM CYCLISATION-ANION CAPTURE PROCESSES. STEREOSPECIFIC GROUP TRANSFER FROM ORGANOZINC AND ORGANOBORON REAGENTS.
Burns, Barry,Grigg, Ronald,Sridharan, Visuvanathar,Stevenson, Paul,Sukirthalingam, Sukanthini,Worakun, Tanachat
, p. 1135 - 1138 (2007/10/02)
Vinyl-, alkyl- and ?-allyl-palladium species arising from regiospecific palladium catalysed 5- or 6-exo-dig or -trig cyclisations onto proximate alkynes, alkenes or dienes can be intercepted stereospecifically by organozinc or organo boron reagents leading to carbo- and hetero-cyclic compounds in moderate to good yield.
