20814-35-1Relevant academic research and scientific papers
Synthesis of quinolines from amino alcohol and ketones catalyzed by [IrCl(cod)]2 or IrCl3 under solvent-free conditions
Taguchi, Kazuhiko,Sakaguchi, Satoshi,Ishii, Yasutaka
, p. 4539 - 4542 (2005)
2-Aminobenzyl alcohol reacted with 2 equiv amount of ketones under the influence of [IrCl(cod)]2 or IrCl3 and KOH without any solvent, giving the corresponding quinoline derivatives in good yields.
IBX-Promoted Oxidative Cyclization of N-Hydroxyalkyl Enamines: A Metal-Free Approach toward 2,3-Disubstituted Pyrroles and Pyridines
Gao, Peng,Chen, Huai-Juan,Bai, Zi-Jing,Zhao, Mi-Na,Yang, Desuo,Wang, Juan,Wang, Ning,Du, Lele,Guan, Zheng-Hui
, p. 7939 - 7951 (2020/07/16)
An iodoxybenzoic acid-mediated selected oxidative cyclization of N-hydroxyalkyl enamines was developed. Through this strategy, a variety of 2,3-disubstituted pyrroles and pyridines were produced in good selectivity involving oxidation of alcohol, followed by condensation of aldehyde and α-C of enamines. Furthermore, this metal-free method has several advantages, including the use of environmentally friendly reagents, broad substrate scope, mild reaction conditions, and high efficiency.
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.
Synthesis of 1,2,3-Substituted Pyrroles from Propargylamines via a One-Pot Tandem Enyne Cross Metathesis-Cyclization Reaction
Chachignon, Helene,Scalacci, Nicoloì,Petricci, Elena,Castagnolo, Daniele
, p. 5287 - 5295 (2015/05/27)
Enyne cross metathesis of propargylamines with ethyl vinyl ether enables the one-pot synthesis of substituted pyrroles. A series of substituted pyrroles, bearing alkyl, aryl, and heteroaryl substituents, has been synthesized in good yields under microwave irradiation. The reactions are rapid and procedurally simple and also represent a facile entry to the synthetically challenging 1,2,3-substituted pyrroles. The value of the methodology is further corroborated by the conversion of pyrroles into 3-methyl-pyrrolines and the derivatization of the 3-methyl-substituent arising from the metathesis reaction.
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.
Rhodium(III)-catalyzed arene and alkene C-H bond functionalization leading to indoles and pyrroles
Stuart, David R.,Alsabeh, Pamela,Kuhn, Michelle,Fagnou, Keith
supporting information; experimental part, p. 18326 - 18339 (2011/03/21)
Recently, the rhodium(III)-complex [Cp*RhCl2]2 1 has provided exciting opportunities for the efficient synthesis of aromatic heterocycles based on a rhodium-catalyzed C-H bond functionalization event. In the present report, the use of complexes 1 and its dicationic analogue [Cp*Rh(MeCN)3][SbF6]2 2 have been employed in the formation of indoles via the oxidative annulation of acetanilides with internal alkynes. The optimized reaction conditions allow for molecular oxygen to be used as the terminal oxidant in this process, and the reaction may be carried out under mild temperatures (60 °C). These conditions have resulted in an expanded compatibility of the reaction to include a range of new internal alkynes bearing synthetically useful functional groups in moderate to excellent yields. The applicability of the method is exemplified in an efficient synthesis of paullone 3, a tetracyclic indole derivative with established biological activity. A mechanistic investigation of the reaction, employing deuterium labeling experiments and kinetic analysis, has provided insight into issues of reactivity for both coupling partners as well as aided in the development of conditions for improved regioselectivity with respect to meta-substituted acetanilides. This reaction class has also been extended to include the synthesis of pyrroles. Catalyst 2 efficiently couples substituted enamides with internal alkynes at room temperature to form trisubstituted pyrroles in good to excellent yields. The high functional group compatibility of this reaction enables the elaboration of the pyrrole products into a variety of differentially substituted pyrroles.
Synthesis of 2,3-disubstituted pyrroles from 3,N-dilithio-N-(tert-butyldimethylsilyl)-2-buten-1-amine
Jacobson, Madeleine A.,Williard, Paul G.
, p. 32 - 37 (2007/10/03)
N-(Trialkylsilyl)allylamines can be deprotonated at the cis-vinylic position to yield 3,N-dilithio-N-(trialkylsilyl)allylamines under mild conditions. N-(Trialkylsilyl)allylamines with terminal alkyl substituents were reported not to form dianions under t
1-Aza-1,3-bis(triphenylphosphoranylidene)propane: A Novel =CHCH2N= Synthon
Katritzky, Alan R.,Jiang, Jinlong,Steel, Peter J.
, p. 4551 - 4555 (2007/10/02)
1-Aza-1,3-bis(triphenylphosphoranylidene)propane (3), prepared in situ by the reaction of 1-methyl>benzotriazole (betmip, 4) with methylidenetriphenylphosphorane followed by treatment with butyllithium, enables convenient preparations of 3H-2-benzazepine (7), 2,3-diarylpyrroles 8, and primary allylamines 12 and 13.
PYRROLES FROM KETOXIMES AND ACETYLENE. 30. THE SYNTHESIS OF 3-ALKYL-2-ARYLPYRROLES
Korostova, S. E.,Mikhaleva, A. I.,Sobenina, L. N.,Shevchenko, S. G.,Shcherbakov, V. V.
, p. 1238 - 1241 (2007/10/02)
Conditions were found for the synthesis of 3-alkyl-2-arylpyrroles using the Trofimov reaction at 50-70 deg C both at elevated and atmospheric pressure.O-Vinyloximes and 3H-5-hydroxy-4,5-dihydropyrroles were isolated as intermediates.
