20413-05-2Relevant articles and documents
Magnesium Halide-Catalyzed Synthesis of Oxaspiro[2.5]octenes from a Methylenecyclopropane and Acyl Cyanoalkenes
Ogura, Kazuki,Shibata, Ikuya,Shimazu, Jun-ya,Suzuki, Itaru
supporting information, p. 2785 - 2787 (2021/06/26)
MgX2-catalyzed annulation of methylenecyclopropanes with acyl cyanoalkenes was accomplished to give oxaspiro[2.5]octenes in excellent yields. The reaction proceeded through a rare intramolecular oxa-Michael addition of Mg enolate. The oxaspiro
Substituent-Controlled Divergent Cascade Cycloaddition Reactions of Chalcones and Arylalkynols: Access to Spiroketals and Oxa-Bridged Fused Heterocycles
Chang, Weixing,Kong, Jingyang,Li, Jing,Liu, Lingyan,Wang, Hongkai,Zeng, Tianlong
supporting information, p. 4024 - 4032 (2021/07/12)
Herein, we report substituent-controlled divergent cascade cycloaddition reactions of chalcones and arylalkynols in the presence of PtI2. Depending on the substituent on the chalcone, either spiroketals or oxa-bridged fused heterocycles could be obtained in the ranges of 86–97% and 87–95% yields under identical reaction conditions. Control experiments were carried out to elucidate the origin of the high chemoselectivity. These provide a method for the synthesis of a diverse array of structurally complex oxygen-containing heterocycles. (Figure presented.).
Mild Darzens Annulations for the Assembly of Trifluoromethylthiolated (SCF3) Aziridine and Cyclopropane Structures
Delost, Michael D.,Njardarson, Jon T.
supporting information, p. 6121 - 6125 (2021/08/16)
We report mild new annulation approaches to trisubstituted trifluoromethylthiolated (SCF3) aziridines and cyclopropanes via Darzens inspired protocols. The products of these anionic annulations, rarely studied previously, possess attractive features rendering them valuable building blocks for synthesis platforms. In this study, trisubstituted acetophenone nucleophiles bearing SCF3 and bromine substituents in their α position were shown to undergo [2 + 1] annulations with vinyl ketones and tosyl-protected imines under mild reaction conditions.
Development of Tyrphostin Analogues to Study Inhibition of the Mycobacterium tuberculosis Pup Proteasome System**
Janssen, Guido V.,Zhang, Susan,Merkx, Remco,Schiesswohl, Christa,Chatterjee, Champak,Darwin, K. Heran,Geurink, Paul P.,van der Heden van Noort, Gerbrand J.,Ovaa, Huib
, p. 3082 - 3089 (2021/09/14)
Tuberculosis is a global health problem caused by infection with the Mycobacterium tuberculosis (Mtb) bacteria. Although antibiotic treatment has dramatically reduced the impact of tuberculosis on the population, the existence and spreading of drug resist
HETEROCYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE INCLUDING SAME
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Paragraph 0142; 0143, (2018/03/10)
The present specification relates to a hetero-cyclic compound and an organic light emitting device comprising the same.
Dienamine-Mediated Asymmetric Inverse-Electron-Demand Hetero-Diels–Alder Reaction of Linear Deconjugated Enones: Diversity-Oriented Synthesis of 3,4-Dihydropyrans
Maity, Rajendra,Pan, Subhas Chandra
supporting information, p. 871 - 874 (2017/02/15)
The first organocatalytic asymmetric inverse-electron-demand Diels–Alder reaction of deconjugated enones by using a linear dienamine was explored. Electron-poor oxadienes having a cyano group were found to be suitable in this reaction. With a 20 mol-% loa
Organocatalytic Asymmetric [4+2] Cycloaddition of 1-Acetylcyclopentene and 1-Acetylcyclohexene for the Synthesis of Fused Carbocycles
Nath, Utpal,Pan, Subhas Chandra
supporting information, p. 6457 - 6461 (2017/12/01)
The first organocatalytic asymmetric [4+2]-cycloaddition reaction of 1-acetylcyclopentenes and 1-acetylcyclohexenes was developed. Enones having cyano groups were used as the dienophiles in this method. The reaction provides a useful practical route to th
Development of 1H-Pyrazolo[3,4-b]pyridines as Metabotropic Glutamate Receptor 5 Positive Allosteric Modulators
Hill, Matthew D.,Fang, Haiquan,Brown, Jeffrey M.,Molski, Thaddeus,Easton, Amy,Han, Xiaojun,Miller, Regina,Hill-Drzewi, Melissa,Gallagher, Lizbeth,Matchett, Michele,Gulianello, Michael,Balakrishnan, Anand,Bertekap, Robert L.,Santone, Kenneth S.,Whiterock, Valerie J.,Zhuo, Xiaoliang,Bronson, Joanne J.,Macor, John E.,Degnan, Andrew P.
supporting information, p. 1082 - 1086 (2016/12/18)
The metabotropic glutamate receptor 5 (mGluR5) is an attractive target for the treatment of schizophrenia due to its role in regulating glutamatergic signaling in association with the N-methyl-d-aspartate receptor (NMDAR). We describe the synthesis of 1H-pyrazolo[3,4-b]pyridines and their utility as mGluR5 positive allosteric modulators (PAMs) without inherent agonist activity. A facile and convergent synthetic route provided access to a structurally diverse set of analogues that contain neither the aryl-acetylene-aryl nor aryl-methyleneoxy-aryl elements, the predominant structural motifs described in the literature. Binding studies suggest that members of our new chemotype do not engage the receptor at the MPEP and CPPHA mGluR5 allosteric sites. SAR studies culminated in the first non-MPEP site PAM, 1H-pyrazolo[3,4-b]pyridine 31 (BMT-145027), to improve cognition in a preclinical rodent model of learning and memory.
One-pot highly diastereoselective annulation to N-unprotected tetrasubstituted 2-pyrrolines
Meninno, Sara,Capobianco, Amedeo,Peluso, Andrea,Lattanzi, Alessandra
supporting information, p. 2137 - 2140 (2015/04/27)
A one-pot DABCO-catalysed Michael addition of glycine imine-derived esters to trans-2-aroyl-3-arylacrylonitriles followed by a deprotection/cyclization/tautomerization sequence afforded tetrasubstituted N-unprotected trans-2-pyrrolines in up to 96% yield.
Reduced graphene oxide supported piperazine in aminocatalysis
Rodrigo, Eduardo,García Alcubilla, Beatriz,Sainz, Raquel,Fierro, J. L. García,Ferritto, Rafael,Cid, M. Belén
supporting information, p. 6270 - 6273 (2014/06/09)
Reduced graphene oxide (rGO) has been used as a support for piperazine to provide a heterogeneous bifunctional organocatalyst (rGO-NH) that is able to efficiently promote vintage organic transformations such as Knoevenagel, Michael and aldol reactions. The obtained results suggest a significant role of the support in the course of these reactions. This journal is the Partner Organisations 2014.