70971-70-9Relevant academic research and scientific papers
Suzuki-Miyaura Cross-Coupling of N-Acylpyrroles and Pyrazoles: Planar, Electronically Activated Amides in Catalytic N-C Cleavage
Meng, Guangrong,Szostak, Roman,Szostak, Michal
supporting information, p. 3596 - 3599 (2017/07/15)
The formation of C-C bonds from amides by catalytic activation of the amide bond has been thus far possible by steric distortion. Herein, we report the first example of a general Pd-catalyzed Suzuki-Miyaura cross-coupling of planar amides enabled by the combination of (i) electronic-activation of the amide nitrogen in N-acylpyrroles and pyrazoles and (ii) the use of a versatile Pd-NHC catalysis platform. The origin and selectivity of forming acylmetals, including the role of twist, are discussed.
Ni-Catalyzed cross-coupling reactions of N-acylpyrrole-type amides with organoboron reagents
Huang, Pei-Qiang,Chen, Hang
supporting information, p. 12584 - 12587 (2017/11/30)
The catalytic conversion of amides to ketones is highly desirable yet challenging in organic synthesis. We herein report the first Ni/bis-NHC-catalyzed cross-coupling of N-acylpyrrole-type amides with arylboronic esters to obtain diarylketones. This method is facilitated by a new chelating bis-NHC ligand. The reaction tolerates diverse functional groups on both arylamide and arylboronic ester partners including sensitive ester and ketone groups.
A practical preparation of highly versatile N-acylpyrroles from 2,4,4-trimethoxybutan-1-amine
Maehara, Tomoaki,Kanno, Rentaro,Yokoshima, Satoshi,Fukuyama, Tohru
supporting information; experimental part, p. 1946 - 1948 (2012/06/01)
A novel method for the preparation of N-acylpyrrole is described. The method involves condensation of carboxylic acids with 2,4,4-trimethoxybutan-1- amine, followed by acid-mediated cyclization to form the pyrrole ring. The preparative procedure is highly
Synthesis of acyl pyrroles via palladium-catalyzed carbonylative amination of aryl and alkenyl iodides
Ho, Stephanie,Bondarenko, Ganna,Rosa, David,Dragisic, Bojan,Orellana, Arturo
experimental part, p. 2008 - 2012 (2012/04/17)
A palladium-catalyzed synthesis of acyl pyrroles from aryl and alkenyl iodides is reported. This carbonylative amination requires only atmospheric (balloon) pressure of carbon monoxide and proceeds with Pd(PPh3) 4 and Pd-NHC catalyst
Unique chemoselective Clauson-Kass reaction of substituted aniline catalyzed by MgI2 etherate
Zhang, Xingxian,Shi, Junchen
experimental part, p. 898 - 903 (2011/03/19)
Clauson-Kass reaction of various substituted aniline, primary aryl amide, and sufonyl amide with 2,5-dimethoxytetrahydrofuran was realized in the presence of 10 mol % of MgI2 etherate in a mild, efficient, and highly chemoselective manner. Iodide counterion and solvents (i.e., MeCN) played the critical roles for the unique reactivity of this catalytic system.
Iron-catalyzed inexpensive and practical synthesis of N-substituted pyrroles in water
Azizi, Najmedin,Khajeh-Amiri, Alireza,Ghafuri, Hossein,Bolourtchian, Mohammad,Saidi, Mohammad Reza
experimental part, p. 2245 - 2248 (2009/12/03)
An operationally simple, practical, and economical protocol for iron(III) chloride catalyzed Paal-Knorr pyrrole synthesis in water in good to excellent yields has been developed. Several N-substituted pyrroles are readily prepared from the reaction of 2,5-dimethoxytetrahydrofuran and aryl/alkyl, sulfonyl and acyl amines under very mild reaction conditions. Georg Thieme Verlag Stuttgart.
Synthesis and nuclear magnetic resonance spectroscopic studies of 1- arylpyrroles
Lee, Chang Kiu,Jun, Jung Ho,Yu, Ji Sook
, p. 15 - 24 (2007/10/03)
A series of m- and p-substituted 1-phenyl, 1-benzyl, 1-benzoyl, and 1- (2-phenylethyl)pyrroles was prepared and their 1H and 13C nmr spectroscopic characteristics were examined. In general, good correlations were observed between the chemical shift values of the β-H and the β-C of pyrroles [except 1-(2-phenylethyl)pyrroles] and the Hammettt σ. The observation may be explained in terms of the electronic effects of the substituents which are transmitted through bonds and through space by interaction of the p orbitals between β-Cs of the pyrrole ring and m- and p- Cs of the phenyl ring. Substituent constants of 1-pyrrolyl, 1-pyrrolylmethyl, and 1-pyrroloyl groups for the 1H and 13C chemical shifts of phenyl ring are also presented.
