62506-80-3Relevant academic research and scientific papers
Synthesis of 1-Pyrroline by Denitrogenative Ring Expansion of Cyclobutyl Azides under Thermal Conditions
Ban, Kazuho,Miki, Yuya,Sajiki, Hironao,Sawama, Yoshinari,Tomita, Naohito
, p. 3481 - 3484 (2021/06/17)
We herein report an efficient and systematic synthesis of 1-pyrrolines from cyclobutyl azides under thermal and neutral conditions. The reaction proceeded without any additional reagents, and nitrogen was generated as the sole by-product. Furthermore, the generated 1-pyrrolines could be continuously transformed into pyrroles, N-Boc-amines, and oxaziridines in an one-pot manner. (Figure presented.).
Transformation of the non-selective aminocyclohexanol-based Hsp90 inhibitor into a Grp94-seletive scaffold
Mishra, Sanket J.,Ghosh, Suman,Stothert, Andrew R.,Dickey, Chad A.,Blagg, Brian S. J.
, p. 244 - 253 (2017/12/30)
Glucose regulated protein 94 kDa, Grp94, is the endoplasmic reticulum (ER) localized isoform of heat shock protein 90 (Hsp90) that is responsible for the trafficking and maturation of toll-like receptors, immunoglobulins, and integrins. As a result, Grp94 has emerged as a therapeutic target to disrupt cellular communication, adhesion, and tumor proliferation, potentially with fewer side effects compared to pan-inhibitors of all Hsp90 isoforms. Although, the N-terminal ATP binding site is highly conserved among all four Hsp90 isoforms, recent cocrystal structures of Grp94 have revealed subtle differences between Grp94 and other Hsp90 isoforms that has been exploited for the development of Grp94-selective inhibitors. In the current study, a structure-based approach has been applied to a Grp94 nonselective compound, SNX 2112, which led to the development of 8j (ACO1), a Grp94-selective inhibitor that manifests -440 nM affinity and ≥200-fold selectivity against cytosolic Hsp90 isoforms.
Substituted pyrrole synthesis from nitrodienes
Karimi, Sasan,Ma, Shuai,Liu, Yanan,Ramig, Keith,Greer, Edyta M.,Kwon, Kitae,Berkowitz, William F.,Subramaniam, Gopal
, p. 2223 - 2227 (2017/05/16)
Though the Cadogan-Sundberg approach has been employed to synthesize a variety of indole and carbazole derivatives from nitroarenes, surprisingly, very little is reported for making pyrroles using the same approach from non-arene nitrodienes. Herein, we report a general method to synthesize substituted pyrroles, in one step with modest yields, from nitrodienes using triphenylphosphine in the presence of an Mo catalyst, bis(acetylaceto)dioxomolybdenum (VI). To shed light on the mechanism of this reaction, we performed DFT calculations using uB3LYP/6-31+G(d) basis set and observed that the reaction favors a path through a nitrene intermediate.
Transition-metal-free trifluoromethylthiolation of n-heteroarenes
Honeker, Roman,Ernst, Johannes B.,Glorius, Frank
supporting information, p. 8047 - 8051 (2015/05/27)
A general and efficient methodology for the direct transition metal free trifluoromethylthiolation of a broad range of biologically relevant N-heteroarenes is reported employing abundant sodium chloride as the catalyst. This method is operationally simple, exhibits high functional group tolerance, and does not require protecting groups. A pinch of salt: A general and efficient methodology for the direct transition-metal-free trifluoromethylthiolation of a broad range of biologically relevant N-heteroarenes is reported employing abundant sodium chloride as the catalyst. This method is operationally simple, exhibits high functional group tolerance, and does not require protecting groups.
Direct synthesis of aryl substituted pyrroles from calcium carbide: An underestimated chemical feedstock?
Kaewchangwat, Narongpol,Sukato, Rangsarit,Vchirawongkwin, Viwat,Vilaivan, Tirayut,Sukwattanasinitt, Mongkol,Wacharasindhu, Sumrit
, p. 460 - 465 (2018/04/16)
In this work, a novel synthetic methodology for the preparation of aryl pyrroles directly from the reaction of calcium carbide with oxime is reported. Various pyrrole derivatives are generated from the corresponding oximes in satisfactory yields (49–88%) under the optimized conditions. The one-pot synthesis of aryl pyrrole from widely available ketone is also successfully developed. A new near-infrared fluorescent BODIPY dye containing a phenyl substitution at the C-3 position is expediently prepared from the aryl pyrrole derived from this methodology. The key benefit of this methodology is the use of an inexpensive and less hazardous primary chemical feedstock, calcium carbide, in a wet solvent without any metal catalysts. This process offers a novel cost-efficient route for the synthesis of functionalized pyrrole.
Copper-catalyzed 5-endo-trig cyclization of ketoxime carboxylates: A facile synthesis of 2-arylpyrroles
Du, Wei,Zhao, Mi-Na,Ren, Zhi-Hui,Wang, Yao-Yu,Guan, Zheng-Hui
, p. 7437 - 7439 (2014/07/07)
A novel and facile copper-catalyzed 5-endo-trig cyclization of ketoxime carboxylates for the synthesis of 2-arylpyrroles has been developed. The reaction tolerates a range of functional groups and is a practical procedure for rapid synthesis of 2-arylpyrroles in high yields under mild conditions. the Partner Organisations 2014.
Synthesis and optical properties of difluorobora-s-diazaindacene dyes with trifluoromethyl meso-substituents
Sobenina, Lyubov N.,Petrova, Olga V.,Petrushenko, Konstantin B.,Ushakov, Igor A.,Mikhaleva, Albina I.,Meallet-Renault, Rachel,Trofimov, Boris A.
, p. 4107 - 4118 (2013/07/19)
A series of meso-CF3-4,4-difluoro-4-bora-3a,4a-diaza-s-indacene (BODIPY) dyes with aryl and hetaryl substituents at the C-3 and C-5 positions, both symmetric and asymmetric, have been synthesized in 36-90 % yields by a new strategy involving as the key step the condensation of 2,2,2-trifluoro-1-(5- arylpyrrol-2-yl)-1-ethanols with diverse 2-arylpyrroles. The starting 2,2,2-trifluoro-1-(5-arylpyrrol-2-yl)-1-ethanols are easily prepared by reduction of the available 2-trifluoroacetyl-5-arylpyrroles. The synthesized dyes fluoresce in a longer wavelength region (626-698 nm) with high quantum yield (0.84-0.99). A new strategy for the synthesis of highly efficient symmetric and asymmetric BODIPY fluorophores that combine trifluoromethyl and 3,5-aryl substituents has been developed. The key step is the P 2O5-promoted condensation of 2,2,2-trifluoro-1-(5- arylpyrrol-2-yl)-1-ethanols with diverse 2-arylpyrroles. Copyright
Direct arylation of arene and N -heteroarenes with diaryliodonium salts without the use of transition metal catalyst
Wen, Jun,Zhang, Ruo-Yi,Chen, Shan-Yong,Zhang, Ji,Yu, Xiao-Qi
experimental part, p. 766 - 771 (2012/02/16)
A novel and simple transition metal-free direct arylation of arene and N-heteroarenes with diaryliodonium salts has been developed. This cross-coupling reaction is promoted only by base and gives the desired products in moderate to good yields.
Catalytic C-H arylation of unactivated heteroaromatics with aryl halides by cobalt porphyrin
Qian, Ying Ying,Wong, Ka Lai,Zhang, Meng Wen,Kwok, Tsz Yiu,To, Ching Tat,Chan, Kin Shing
supporting information; experimental part, p. 1571 - 1575 (2012/04/11)
Direct C-H arylation of unactivated heteroaromatics with aryl halides catalyzed by cobalt porphyrin is reported. The reaction is proposed to go through a homolytic aromatic substitution reaction. The aryl radical is electrophilic and a SOMO-HOMO interaction is predominant in the aryl radical addition process.
Iron-mediated direct suzuki-miyaura reaction: A new method for the ortho -arylation of pyrrole and pyridine
Wen, Jun,Qin, Song,Ma, Li-Fang,Dong, Liang,Zhang, Ji,Liu, Shan-Shan,Duan, Yi-Shu,Chen, Shan-Yong,Hu, Chang-Wei,Yu, Xiao-Qi
supporting information; experimental part, p. 2694 - 2697 (2010/09/03)
(Figure presented) The first example of an iron-mediated direct Suzuki-Miyaura reaction between N-heterocyclic compounds and arylboronic acids is described, and both electron-rich and electron-deficient heteroarenes can be successfully used for the coupling reaction.
