837-56-9Relevant academic research and scientific papers
Synthesis of 2-Monosubstituted Pyrroles by Intramolecular Addition of Amines via Reductive Amination with Dibutyliodotin Hydride Complex (Bu 2SnIH-HMPA)
Shibata, Ikuya,Kato, Hirofumi,Kanazawa, Nobuaki,Yasuda, Makoto,Baba, Akio
, p. 137 - 139 (2004)
Various 2-monosubstituted pyrroles were prepared in a one-pot procedure via the reductive amination of formyl groups of multifunctional substrates 1 by using Bu2SnIH-HMPA system.
Copper-catalyzed pyrrole synthesis from 3,6-dihydro-1,2-oxazines
Yasukawa, Naoki,Kuwata, Marina,Imai, Takuya,Monguchi, Yasunari,Sajiki, Hironao,Sawama, Yoshinari
supporting information, p. 4409 - 4413 (2018/10/17)
Highly-functionalized pyrroles could be effectively synthesized from 3,6-dihydro-1,2-oxazines using a heterogeneous copper on carbon (Cu/C) under neat heating conditions. Furthermore, the in situ formation of 3,6-dihydro-1,2-oxazines via the hetero Diels-Alder reaction between nitroso dienophiles and 1,3-dienes and the following Cu/C-catalyzed pyrrole synthesis also provided the corresponding pyrrole derivatives in a one-pot manner.
Regioisomeric and Substituent Effects upon the Outcome of the Reaction of 1-Borodienes with Nitrosoarene Compounds
Eberlin, Ludovic,Carboni, Bertrand,Whiting, Andrew
, p. 6574 - 6583 (2015/10/06)
A study of the reactivity of 1-borodienes with nitrosoarene compounds has been carried out showing an outcome that differs according to the hybridization state of the boron moiety. Using an sp2 boron substituent, a one-pot hetero-Diels-Alder/ring contraction cascade occurred to afford N-arylpyrroles with low to good yields depending on the electronic properties of the substituents on the borodiene, whereas an sp3 boron substituent led to the formation of stable boro-oxazines with high regioselectivity in most of the cases, in moderate to good yields. 1H and 11B NMR studies on two boro-oxazine regioisomers showed that selective deprotection can be performed. Formation of either the pyrrole or the furan derivative is pH- and regioisomer-structure-dependent. The results obtained, together with previous B3LYP calculations, support mechanistic proposals which suggest that pyrrole, or furan, formation proceeds via oxazine formation, followed by a boryl rearrangement and an intramolecular addition-elimination sequence.
Synthesis of polysubstituted pyrroles via Pd-catalyzed oxidative alkene C-H bond arylation and amination
Zheng, Jia,Huang, Liangbin,Huang, Chuyu,Wu, Wanqing,Jiang, Huanfeng
, p. 1235 - 1242 (2015/01/30)
A novel Pd(II)-catalyzed oxidative approach to construct polysubstituted pyrroles from N-homoallylicamines and arylboronic acids was developed. This transformation is supposed to proceed through cascade formation of C-C and C-N bonds via oxidative arylation of unactive alkenes, followed by intramolecular aza-Wacker cyclization.
β-selective C-H arylation of pyrroles leading to concise syntheses of lamellarins C and I
Ueda, Kirika,Amaike, Kazuma,Maceiczyk, Richard M.,Itami, Kenichiro,Yamaguchi, Junichiro
, p. 13226 - 13232 (2015/03/30)
The first general β-selective C-H arylation of pyrroles has been developed by using a rhodium catalyst. This C-H arylation reaction, which is retrosynthetically straightforward but results in unusual regioselectivity, could result in de novo syntheses of
Base-mediated intermolecular sp2 C-H bond arylation via benzyne intermediates
Truong, Thanh,Daugulis, Olafs
supporting information; experimental part, p. 4243 - 4245 (2011/06/21)
A transition-metal-free method for arylation of heterocycle and arene carbon-hydrogen bonds by aryl chlorides and fluorides has been developed. The reactions proceed via aryne intermediates and are highly regioselective with respect to the C-H bond coupling component.
Palladium-catalyzed indole, pyrrole, and furan arylation by aryl chlorides
Nadres, Enrico T.,Lazareva, Anna,Daugulis, Olafs
experimental part, p. 471 - 483 (2011/04/15)
The palladium-catalyzed direct arylation of indoles, pyrroles, and furans by aryl chlorides has been demonstrated. The method employs a palladium acetate catalyst, 2-(dicyclohexylphosphino)-biphenyl ligand, and an inorganic base. Electron-rich and electron-poor aryl chlorides as well as chloropyridine coupling partners can be used, and arylated heterocycles are obtained in moderate to good yields. Optimization of base, ligand, and solvent is required for achieving best results.
Palladium-catalyzed decarboxylative cross-coupling reaction between heteroaromatic Carboxylic acids and Aryl halides
Bilodeau, Francois,Brochu, Marie-Christine,Guimond, Nicolas,Thesen, Kris H.,Forgione, Pat
experimental part, p. 1550 - 1560 (2010/06/12)
"Chemical Equation Presented" A full overview of the decarboxylative cross-coupling reaction between heteroaromatic carboxylic acids and aryl halides is described. This transformation employs palladium catalysts with short reaction times providing facile synthesis of aryl-substituted heteroaromatics. The effect of each reaction parameter including solvent, base, and additive employed as well as the full substrate scope of this transformation are reported. Mechanistic evidence is also disclosed that sheds light on possible reaction pathways.
One-pot synthesis of heterocyclic compounds initiated by chemoselective addition to β-acyl substituted unsaturated aldehydes with nucleophilic tin complexes
Shibata, Ikuya,Kato, Hirofumi,Yasuda, Makoto,Baba, Akio
, p. 604 - 619 (2008/02/06)
β-Acyl substituted unsaturated aldehydes 1 were revealed to be good precursors for the synthesis of various heterocyclic compounds by the combination with tin nucleophiles. Various 2-monosubstituted pyrroles were prepared in an one-pot procedure via the reductive amination of formyl groups of 1 by using Bu2SnIH-HMPA complex. One-pot synthesis of heterocycles was carried out initiated by chemoselective reduction of 1 with Bu3SnH-HMPA complex and the subsequent reaction with heterocumulenes. Furthermore, the one-pot synthesis of nitrogen heterocyclic compounds accompanying chemo-, regio- and diastereoselective carbon-carbon bond formation in side chain moieties was effectively accomplished initiated by the regio- and diastereoselective allylation of the formyl group of 1 with allylic tin species.
Synthesis of N-substituted 2-arylpyrroles by the reaction of (η2-imine)titanium complexes with 3,3-diethoxypropyne
Ohkubo, Mutsumi,Hayashi, Daisuke,Oikawa, Daisuke,Fukuhara, Kouki,Okamoto, Sentaro,Sato, Fumie
, p. 6209 - 6212 (2007/10/03)
(η2-Imine)Ti(O-i-Pr)2 complexes generated from arylaldehyde imines and a divalent titanium reagent, Ti(O-i-Pr)4/2i-PrMgCl, reacted with 3,3-diethoxypropyne to afford 2-arylpyrroles.
