85814-61-5Relevant academic research and scientific papers
Green multicomponent reaction for synthesis of trisubstituted pyrroles in ionic liquid [bmim]BF4
Reddy, G. Narshimha,Likhar, Pravin R.
, p. 6873 - 6879 (2016/08/25)
2,4,5-Trisubstituted pyrrole derivatives were efficiently synthesized by one-pot condensation of 1,3-diones, α-bromoacetophenones, and ammonium acetate in ionic liquid [bmim]BF4. The new synthetic method offers multisubstituted pyrroles with th
I2-DMSO promoted metal free oxidative cyclization for the synthesis of substituted Indoles and pyrroles
Ramakrishnam Raju, Addada,Venkata Reddy, Regalla,Mallikarjuna Rao, Vajja,Venkata Naresh, Vema,Venkateswara Rao, Anna
supporting information, p. 2838 - 2841 (2016/06/14)
A series of di substituted indole and tri substituted pyrrole derivatives were synthesized efficiently by using I2/K2CO3 in DMSO. The novel synthesis method offers the advantage of mild reaction conditions, operational simplicity, higher yields. The method is functional group tolerant and provides quick access to medicinally significant compounds in moderate to high yields.
Microwave-assisted facile synthesis of trisubstituted pyrrole derivatives
Hanuman Reddy,Mallikarjuna Reddy,Thirupalu Reddy,Rami Reddy
, p. 9805 - 9815 (2015/03/14)
We report efficient synthesis of pyrrole derivatives by use of microwave irradiation. Quantitative yields were obtained in short reaction times. Low yields of product were obtained from alicyclic amino unsaturated ketone derivatives; higher yields were ob
Visible-light-induced formal [3+2] cycloaddition for pyrrole synthesis under metal-free conditions
Xuan, Jun,Xia, Xu-Dong,Zeng, Ting-Ting,Feng, Zhu-Jia,Chen, Jia-Rong,Lu, Liang-Qiu,Xiao, Wen-Jing
, p. 5653 - 5656 (2014/06/10)
A photocatalytic formal [3+2] cycloaddition of 2H-azirines with alkynes has been achieved under irradiation by visible light in the presence of organic dye photocatalysts. This transformation provides efficient access to highly functionalized pyrroles in good yields and has been applied to the synthesis of drug analogues. A primary trial of photocascade catalysis merging energy transfer and redox neutral reactions was shown to be successful. Photo(chemistry) op: A photocatalytic formal [3+2] cycloaddition of 2H-azirines with alkynes has been established under the irradiation of visible light in the presence of an organic dye. This transformation provides efficient access to highly functionalized pyrroles in good yields and has been applied to the formal synthesis of an inhibitor for HMG-CoA reductase.
Cu(OTf)2-catalyzed synthesis of 2,3-disubstituted indoles and 2,4,5-trisubstituted pyrroles from α-diazoketones
Reddy, B. V. Subba,Reddy, M. Ramana,Rao, Y. Gopal,Yadav,Sridhar
supporting information, p. 464 - 467 (2013/04/10)
A novel method has been devised for the synthesis of 2,4,5-trisubstituted pyrrole derivatives through the coupling of α-diazoketones with β-enaminoketones and esters using 10 mol % of Cu(OTf)2. A wide range of 2,3-disubstituted indole derivatives were also prepared from α-diazoketones and 2-aminoaryl or alkyl ketones. The synthetic versatility of this approach has been exemplified in the formal synthesis of homofascaplysin C.
Development of a gold-multifaceted catalysis approach to the synthesis of highly substituted pyrroles: Mechanistic insights via Huisgen cycloaddition studies
Ngwerume, Simbarashe,Lewis, William,Camp, Jason E.
, p. 920 - 934 (2013/04/10)
A novel gold-catalyzed method for the regioselective synthesis of highly substituted pyrroles directly from oximes and alkynes was developed via independent optimization of two key steps of the process. Importantly, a cationic gold(I) species was shown to activate multiple steps along the reaction pathway and therefore act as a multifaceted catalyst. Initial gold-promoted addition of the oxime oxygen to the activated alkyne afforded the O-vinyloxime in situ. The O-vinyloxime was subsequently transformed into the pyrrole via a gold-catalyzed tautomerization, [3,3]-sigmatropic rearrangement, and cyclodehydration process. Notably, this method provides a functional group handle in the form of an ester at the 3/4-position for further exploitation. The proposed mechanistic pathway is supported by a novel application of the Huisgen cycloaddition click reaction, which was used to probe the relative stability of substituted O-vinyloximes. The intermediacy of N-alkenylhydroxylamine O-vinyl ethers and imino ketones or imino aldehydes along the reaction pathway were determined by high-temperature 1H, 2H{1H}, and 13C{1H} NMR experiments. X-ray crystallographic evidence was used to further support the mechanistic hypothesis.
Role of imino group in photochemical reactions of Fischer carbene complexes
Campos, Pedro J.,Caro, Míriam,López-Sola, Susana,Sampedro, Diego,Rodríguez, Miguel A.
, p. 1075 - 1080 (2007/10/03)
The photochemical cycloaddition of Fischer iminecarbene complexes bearing two kinds of substituent, imine and alkoxy or amino, has been explored with alkenes and alkynes. It was found that annulated product without CO insertion is formed.
Lewis base effects in the Baylis-Hillman reaction of imines with methyl vinyl ketone
Shi, Min,Xu, Yong-Mei
, p. 696 - 701 (2007/10/03)
In the Baylis-Hillman reaction of N-benzylidene-4-methyl-benzenesulfonamide with methyl vinyl ketone (MVK), we found that, in the presence of a catalytic amount of DMAP, PPh3 or DABCO as Lewis base, the Baylis-Hillman reaction can be greatly ac
Studies on cycloaddition reactions of 1,3-diphenyl-2-azaallyl lithium and ethyl (benzylideneamino) acetate anion with α-oxoketene dithioacetals
Balu, Maliakel P.,Ila, Hiriyakkanavar,Junjappa, Hiriyakkanavar
, p. 6771 - 6782 (2007/10/02)
The α-oxoketene dithioacetals undergo anionic [1,3] cycloaddition with 1,3-diphenyl-2-azaallyllithium to give either pyrroles or spiropyrrolines with two exceptions. Lithium bromide/triethylamine induced cycloaddition of ethyl (benzylideneamino)acetate (7
Oxidative Halogenation of Substituted Pyrroles with Cu(II). Part I. Bromination of some 3-Acetylpyrroles
Petruso, S.,Caronna, S.,Sprio, V.
, p. 1209 - 1211 (2007/10/02)
3-Acetylpyrroles are brominated with copper(II) bromide.The reaction afforded almost quantitatively only nuclear monobromination.Evidence for the structures of final compounds was by mass spectrometry, 1H-nuclear magnetic resonance, ir, and elemental analysis.
