scholarly journals Pyrrole–Aminopyrimidine Ensembles: Cycloaddition of Guanidine to Acylethynylpyrroles

Molecules ◽  
2021 ◽  
Vol 26 (6) ◽  
pp. 1692
Author(s):  
Olga V. Petrova ◽  
Arsalan B. Budaev ◽  
Elena F. Sagitova ◽  
Igor A. Ushakov ◽  
Lyubov N. Sobenina ◽  
...  
Keyword(s):  
Efficient Method ◽  
Triple Bond ◽  
Pyrrole Ring ◽  
Dmso System ◽  
Guanidine Nitrate ◽  
Reaction Proceeds

An efficient method for the synthesis of pharmaceutically prospective pyrrole–aminopyrimidine ensembles (in up to 91% yield) by the cyclocondensation of easily available acylethynylpyrroles with guanidine nitrate has been developed. The reaction proceeds under heating (110–115 °C, 4 h) in the KOH/DMSO system. In the case of 2-benzoylethynylpyrrole, the unexpected addition of the formed pyrrole–aminopyrimidine as N- (NH moiety of the pyrrole ring) and C- (CH of aminopyrimidine) nucleophiles to the triple bond is observed.

scholarly journals Microwave-assisted urea catalyzed Knoevenagel condensation of aldehydes with active methylene compounds

2020 ◽  
Vol 55 (2) ◽  
pp. 159-164
Author(s):  
WT Purba ◽  
PS Roy ◽  
S Jannat ◽  
SA Begum ◽  
MM Rahman
Keyword(s):  
Microwave Irradiation ◽  
Efficient Method ◽  
Knoevenagel Condensation ◽  
Efficient Catalyst ◽  
Microwave Assisted ◽  
Solvent Free Conditions ◽  
Wide Range ◽  
Active Methylene Compounds ◽  
Reaction Proceeds ◽  
Active Methylene

Rapid and efficient method for the synthesis of substituted olefins such as 2-(4-chlorophenylmethylene) malononitrile, 2-(4-hydroxyphenylmethylene) malononitrile and 2-cyano-3-(4-hydroxyphenyl) acrylamide etc under the influence of microwave irradiation are described. Urea has been utilized as an efficient catalyst for the Knoevenagel condensation of aldehydes with acidic active methylene compounds such as malononitrile, ethylcyanoacetate and cyanoacetamide to afford substituted olefins under the influence of microwave irradiation. The reaction proceeds smoothly under mild and solvent free conditions and the products are obtained in good yield. The method is applicable for a wide range of aldehydes including aromatic and heterocyclic substrates. Bangladesh J. Sci. Ind. Res.55(2), 159-164, 2020

Copper(II)-Promoted Oxidation/[3+2]Cycloaddition/Aromatization Cascade: Efficient Synthesis of Tetrasubstituted NH-Pyrrole from Chalcones and Iminodiacetates

Synlett ◽  
2019 ◽  
Vol 30 (12) ◽  
pp. 1442-1446 ◽  
Author(s):  
Zhang-qi Lin ◽  
Chao-dong Li ◽  
Zi-chun Zhou ◽  
Shuai Xue ◽  
Jian-rong Gao ◽  
...  
Keyword(s):  
Efficient Method ◽  
Cascade Reaction ◽  
Oxidative Cyclization ◽  
Efficient Synthesis ◽  
Reaction Conditions ◽  
Highly Efficient ◽  
Wide Range ◽  
Reaction Proceeds

A simple and highly efficient method for the preparation of tetrasubstituted NH-pyrrole from a wide range of chalcones and diethyl iminodiacetates via a Cu(OAc)2-promoted oxidation/[3+2]cycloaddition/aromatization cascade reaction has been developed. This reaction proceeds through dehydrogenations, deamination, and oxidative cyclization, affording the corresponding products in good to excellent yields. This convenient methodology for constructing tetrasubstituted NH-pyrroles has several advantages over existing methods, such as the use of easily accessible chalcones and readily available diethyl iminodiacetates, and mild reaction conditions. A wide range of substrates are tolerated.

Chemoselective catalytic reduction of conjugated α,β-unsaturated ketones to saturated ketones via a hydroboration/protodeboronation strategy

2016 ◽  
Vol 3 (1) ◽  
pp. 14-18 ◽  
Author(s):  
Wen Ding ◽  
Qiuling Song
Keyword(s):  
Metal Hydride ◽  
Triple Bond ◽  
Catalytic Reduction ◽  
Hydrogen Gas ◽  
Single Bond ◽  
Unsaturated Ketones ◽  
Reaction Proceeds

A novel copper-catalyzed chemoselective reduction of a carbon–carbon double or triple bond to a carbon–carbon single bond on α,β-unsaturated ketones is developed, this reaction proceeds under hydrogen gas or stoichiometric metal hydride free conditions.

Functionalized Bipyrroles and Pyrrolyl-Aminopyrones from Acylethynylpyrroles and Diethyl Aminomalonate

Synthesis ◽  
2021 ◽  
Author(s):  
Maxim Gotsko ◽  
Ivan Saliy ◽  
Luybov Sobenina ◽  
Igor Ushakov ◽  
Viktoria Kireeva ◽  
...  
Keyword(s):  
Nitrogen Atom ◽  
Efficient Method ◽  
Reaction Proceeds

An efficient method for the synthesis of 1H,1’H-2,3’-bipyrroles (in up to 72% yield) by the cyclocondensation of easily available 2-(acylethynyl)pyrroles with diethyl aminomalonate hydrochloride has been developed. The reaction proceeds under reflux in MeCN (6 h) in the presence of Cs2CO3. Under the same conditions, 2-(acylethynyl)pyrroles with bulky (benzyl and octyl) substituents at nitrogen atom react with diethyl aminomalonate to afford 1H,2’H-2,3’-bipyrroles and pyrrolyl-aminopyrones.

Convenient one-pot multicomponent strategy for the synthesis of 6-pyrrolylpyrimidines

RSC Advances ◽  
2014 ◽  
Vol 4 (56) ◽  
pp. 29493-29501 ◽  
Author(s):  
Pandi Dhanalakshmi ◽  
Sivakumar Shanmugam
Keyword(s):  
One Pot ◽  
Easy Method ◽  
Guanidine Nitrate ◽  
Reaction Proceeds ◽  
Methyl Isocyanide ◽  
High Yields

An easy method to construct diheteroaryls from α-aroylidineketene dithioacetals 2 in a multicomponent fashion. The reaction proceeds with high chemo/regioselectivity to give 4-alkoxy-6-(4-aryl-1H-pyrrol-3-yl)pyrimidin-2-amines in high yields by reacting 2 with p-tolylsulfonyl)methyl isocyanide 3 (TosMIC), guanidine nitrate 5 and alcohol in the presence of NaH/THF via cycloaddition.

Copper complexes and carbon nanotube–copper ferrite-catalyzed benzenoid A-ring selenation of quinones: an efficient method for the synthesis of trypanocidal agents

2019 ◽  
Vol 43 (35) ◽  
pp. 13751-13763 ◽  
Author(s):  
Guilherme A. M. Jardim ◽  
Ícaro A. O. Bozzi ◽  
Willian X. C. Oliveira ◽  
Camila Mesquita-Rodrigues ◽  
Rubem F. S. Menna-Barreto ◽  
...  
Keyword(s):  
Carbon Nanotube ◽  
Efficient Method ◽  
Copper Complexes ◽  
Copper Ferrite ◽  
Trypanocidal Activity ◽  
Reaction Proceeds ◽  
General Method

A-ring selenation of naphthoquinones and anthraquinones is reported. The reaction proceeds in the presence of a copper source, and provides an efficient and general method for preparing selenium-based quinones with trypanocidal activity.

Direct Transformation of Propargylic Alcohols and O,O-Diethyl Phosphorothioic Acid into S-(2H-Chromen-4-yl) Phosphorothioates

Synthesis ◽  
2019 ◽  
Vol 52 (02) ◽  
pp. 208-218
Author(s):  
Xian-Rong Song ◽  
Tao Yang ◽  
Haixin Ding ◽  
Qiang Xiao
Keyword(s):  
Efficient Method ◽  
Environmentally Benign ◽  
Direct Transformation ◽  
Propargylic Alcohols ◽  
Reaction Proceeds

An environmentally benign and efficient method has been successfully developed to generate S-(2H-chromen-4-yl) phosphorothioates from easily available 2-(3-hydroxyprop-1-ynyl)phenols and O,O-diethyl phosphorothioic acid [(EtO)2P(O)SH] with water as the only byproduct. The reaction proceeds smoothly in moderate to excellent yields. It is noted that (EtO)2P(O)SH acts not only as an acid promoter, but also as the nucleophile to attack the allenic carbocation intermediate.

scholarly journals 2-(1-Hydroxypropyn-2-yl)-1-vinylpyrroles: the first successful Favorsky ethynylation of pyrrolecarbaldehydes

2015 ◽  
Vol 11 ◽  
pp. 228-232 ◽  
Author(s):  
A V Ivanov ◽  
V S Shcherbakova ◽  
I A Ushakov ◽  
L N Sobenina ◽  
O V Petrova ◽  
...  
Keyword(s):  
Atmospheric Pressure ◽  
Pyrrole Ring ◽  
Dmso System

1-Vinylpyrrole-2-carbaldehydes react with acetylene at atmospheric pressure in a NaOH/EtOH/DMSO system at 7–10 °C to afford 2-(1-hydroxypropyn-2-yl)-1-vinylpyrroles in 53–94% yield. Thus, the first base-mediated direct ethynylation of pyrrolecarbaldehydes with free acetylene under modified conditions of the Favorsky reaction has been implemented to pave an expedient route to important biomolecules containing a pyrrole ring.

Synthesis of Triazole-Fused Phenanthridines through Pd-Catalyzed Intramolecular Phenyl C–H Activation of 1,5-Diaryl-1,2,3-triazoles

Synlett ◽  
2019 ◽  
Vol 30 (12) ◽  
pp. 1452-1456 ◽  
Author(s):  
Jiazhuang Wang ◽  
Jianhua Yang ◽  
Xuxin Fu ◽  
Guiping Qin ◽  
Tiebo Xiao ◽  
...  
Keyword(s):  
Efficient Method ◽  
Palladium Catalysis ◽  
Reaction Proceeds

An efficient method for the synthesis of triazole-fused phenanthridines from 1,5-diaryl-1,2,3-triazoles under palladium catalysis has been developed. The reaction proceeds through Pd-catalyzed intramolecular phenyl C–H activation of 1,5-diaryl-1,2,3-triazoles. This method provides a concise and efficient pathway to construct triazolo[1,5-f]phenanthridine derivatives in excellent yields.

"Click chemistry" in the synthesis of the first glycoconjugates of bacteriochlorin series

2012 ◽  
Vol 16 (10) ◽  
pp. 1094-1109 ◽  
Author(s):  
Mikhail A. Grin ◽  
Ivan S. Lonin ◽  
Leonid M. Likhosherstov ◽  
Olga S. Novikova ◽  
Anna D. Plyutinskaya ◽  
...  
Keyword(s):  
Click Chemistry ◽  
Cell Line ◽  
Triple Bond ◽  
Pyrrole Ring ◽  
2D Nmr ◽  
Bacteriochlorophyll A ◽  
Dipolar Cycloaddition ◽  
Nmr Analysis ◽  
Hep2 Cell ◽  
Imide Ring

A regioselective synthesis of glycoconjugates based on bacteriochlorophyll a and lactose derivatives has been carried out. The conjugation was achieved via 1,3-dipolar cycloaddition of bacteriochlorins containing a terminal triple bond and a lactose azide derivative. The conjugates obtained in this way had one or two disaccharide fragments attached to pyrrol A, the exocyclic imide ring of the tetrapyrrolyc macrocycle, or to both positions. Exhaustive NMR analysis by 1D and 2D NMR experiments ( 1H-1H COSY, TOCSY, ROESY, 1H-13C HSQC, HMBC, and 1H-15N HMBC) allowed us to determine the structures and configurations of the glycoconjugates obtained. A bioassay of the glycoconjugates using the Hep2 cell line showed that the highest efficiency was observed for the glycosylated bacteriopurpurinimide containing a lactose residue at pyrrole ring A.

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