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.

Highly Selective One-Pot Synthesis of Polysubstituted Isoflavanes using Styryl Ethers and Electron-Withdrawing ortho-Quinone Methides Generated In Situ

Synlett ◽  
2018 ◽  
Vol 30 (02) ◽  
pp. 189-192 ◽  
Author(s):  
Yujiro Hoshino ◽  
Kiyoshi Honda ◽  
Kenta Tanaka ◽  
Mami Kishimoto ◽  
Naoya Ohtsuka ◽  
...  
Keyword(s):  
Biologically Active ◽  
Quinone Methides ◽  
One Pot ◽  
One Pot Synthesis ◽  
Reaction Proceeds ◽  
Acidic Conditions ◽  
High Yields

A highly selective one-pot synthesis of polysubstituted isoflavanes has been developed. The reaction proceeds through the cycloaddition of methyl styryl ethers, derived from phenylacetaldehyde dimethyl acetals under acidic conditions, with electron-withdrawing ortho-quinone methides generated in situ. When phenylacetaldehyde dimethyl acetals were reacted with salicylaldehydes, the reaction proceeded smoothly to afford the corresponding isoflavanes stereoselectively in high yields and with excellent regioselectivities. The present reaction provides versatile access to functionalized isoflavanes, and constitutes a useful tool for the synthesis of biologically active molecules.

Concise Synthesis of Tryptanthrin Spiro Analogues with In Vitro Antitumor Activity Based on One-Pot, Three-Component 1,3-Dipolar Cycloaddition of Azomethine Ylides to Сyclopropenes

Synthesis ◽  
2018 ◽  
Vol 51 (03) ◽  
pp. 713-729 ◽  
Author(s):  
Vitali Boitsov ◽  
Alexander Stepakov ◽  
Alexander Filatov ◽  
Nickolay Knyazev ◽  
Stanislav Shmakov ◽  
...  
Keyword(s):  
Antitumor Activity ◽  
Azomethine Ylides ◽  
Azomethine Ylide ◽  
Dipolar Cycloaddition ◽  
One Pot ◽  
Economic Method ◽  
Reaction Proceeds ◽  
High Yields

A simple, efficient and atom-economic method has been developed for the synthesis of complex alkaloid-like compounds with spiro-fused indolo[2,1-b]quinazoline and cyclopropa[a]pyrrolizine or 3-azabicyclo[3.1.0]hexane moieties. We have found that one-pot, three-component 1,3-dipolar cycloaddition reactions allow the desired products to be obtained from various cyclopropene derivatives with tryptanthrin-derived azomethine ylides generated in situ, in good to high yields and excellent diastereoselectivity. The possibility of ylide generation was exemplified by using α-amino acids (l-proline, l-4-thiazolidincarboxylic acid) and simplest peptides (dipeptide Gly-Gly, tripeptide Gly-Gly-Gly). Quantum chemical investigations indicate that the reaction proceeds through the S-shaped azomethine ylide, the interaction of which with cyclopropenes proceeds via a less sterically hindered endo-transition state. The antitumor activity of some of spiro-tryptanthrin derivatives against erythroleukemia (K562), cervical carcinoma (HeLa) and colon carcinoma (CT26) cell lines was evaluated in vitro by MTS-assay.

One-Pot Sequential Multistep Transformation of α,β-Unsaturated Trifluoromethyl Ketones: Facile Synthesis of Trifluoromethylated 2-Pyridones

Synlett ◽  
2019 ◽  
Vol 30 (05) ◽  
pp. 605-609 ◽  
Author(s):  
Fa-Guang Zhang ◽  
Jun-An Ma ◽  
Ning Lv ◽  
Yi-Qiang Tian
Keyword(s):  
Facile Synthesis ◽  
One Pot ◽  
Good Efficiency ◽  
Trifluoromethyl Ketones ◽  
Mild Conditions ◽  
Efficient Access ◽  
Reaction Proceeds ◽  
High Yields ◽  
Unsaturated Trifluoromethyl Ketones

A one-pot transformation of α,β-unsaturated trifluoromethyl ketones with 2-(phenylsulfinyl)acetamide to give trifluoromethylated 2-pyridones is realized. The reaction proceeds under mild conditions and involves multiple steps in an expeditious and controlled sequence to provide efficient access to a broad range of trifluoromethylated 2-pyridones in moderate to high yields. Moreover, further synthetic manipulations permit the routine synthesis of a diverse array of trifluoromethylated pyridines with good efficiency.

scholarly journals Synthesis of functionalized bicyclic pyridones containing dithiocarbamate group using thioazlactones, diamines and nitroketene dithioacetal

SynOpen ◽  
2021 ◽  
Author(s):  
Marziyeh Saeedi ◽  
maryam khoshdoun ◽  
Salman Taheri ◽  
Azim Ziyaei Halimehjani ◽  
Aliasghar Mohammadi ◽  
...  
Keyword(s):  
Alkylation Reaction ◽  
X Ray Diffraction ◽  
One Pot ◽  
Three Component Reaction ◽  
Reaction Proceeds ◽  
Ketene Dithioacetal ◽  
Ft Ir ◽  
High Yields ◽  
Nitro Ketene Dithioacetal ◽  
Dithiocarbamate Group

An efficient method for the synthesis of highly substituted bicyclic pyridone derivatives containing dithiocarbamate group is reported via a one-pot three-component reaction of 2-(alkylthio) thioazlactones, diamines and nitro ketene dithioacetal in EtOH under catalyst-free conditions. The reaction proceeds via a domino amidation/intramolecular 1,4-addition-type Friedel-Crafts alkylation reaction to afford the corresponding fused bicyclic pyridones with high yields and diastereselectively. The desired products are fully characterized by FT-IR, 1H and 13CNMR, CHN and single crystal X-ray diffraction analyses.

scholarly journals One-Pot Green Method for the Synthesis of Oxazine Derivatives Under Aqueous Medium

2020 ◽  
pp. 332-339
Author(s):  
Santosh R. Kshirsagar ◽  
Ashok S. Pise ◽  
Sagar I. Shinde ◽  
Sandip P. Gondake ◽  
Valmik S. Kapase
Keyword(s):  
Polyphosphoric Acid ◽  
One Pot ◽  
Green Catalyst ◽  
Multicomponent Condensation ◽  
Reaction Proceeds ◽  
High Yields ◽  
Aqueous Conditions ◽  
Harmful Effects ◽  
Environmentally Friendly Method ◽  
Oxazine Derivatives

A simple, convenient, and environmentally friendly method for the synthesis of 1,3-oxazine derivatives has been developed under aqueous conditions. The reaction proceeds via one pot multicomponent condensation of ? or ?- naphthol, aromatic aniline and formaldehyde using polyphosphoric acid as green catalyst. The current protocols are simple, requires less reaction time and provides high yields. Non-polluting synthetic procedures are used to avoid harmful effects of organic solvents on the environment.

An Expeditious One-Pot Three-Component Synthesis of 4-Aryl-3,4-dihydrobenzo[g] quinoline-2,5,10(1H)-triones under Green Conditions

2020 ◽  
Vol 23 (23) ◽  
pp. 2626-2634
Author(s):  
Saiedeh Kamalifar ◽  
Hamzeh Kiyani
Keyword(s):  
Reaction Medium ◽  
Meldrum's Acid ◽  
Meldrum’S Acid ◽  
One Pot ◽  
One Pot Synthesis ◽  
Substituted Benzaldehydes ◽  
High Yields ◽  
First Time ◽  
Green Conditions

: An efficient and facial one-pot synthesis of 4-aryl-3,4-dihydrobenzo[g]quinoline- 2,5,10(1H)-triones was developed for the first time. The process proceeded via the three-component cyclocondensation of 2-amino-1,4-naphthoquinone with Meldrum’s acid and substituted benzaldehydes under green conditions. The fused 3,4-dihydropyridin-2(1H)- one-ring naphthoquinones have been synthesized with good to high yields in refluxing ethanol as a green reaction medium. This protocol is simple and effective as well as does not involve the assistance of the catalyst, additive, or hazardous solvents.

Synthesis of 3-(Cyclohexylamino)-2-arylimidazo[1,2-a]pyridine-8- carboxylic Acids Via an Efficient Three-component Condensation Reaction between Cyclohexylisocyanide and 2-Aminopyridine-3-carboxylic Acid in the Presence of Aromatic Aldehyde

2018 ◽  
Vol 21 (4) ◽  
pp. 298-301 ◽  
Author(s):  
Ghasem Marandi
Keyword(s):  
Biological Sciences ◽  
Carboxylic Acid ◽  
Carboxylic Acids ◽  
High Performance ◽  
Condensation Reaction ◽  
Aromatic Aldehydes ◽  
New Materials ◽  
One Pot ◽  
High Yields ◽  
Benzaldehyde Derivatives

Aim and Objective: The reaction of cyclohexylisocyanide and 2-aminopyridine-3- carboxylic acid in the presence of benzaldehyde derivatives in ethanol led to 3-(cyclohexylamino)-2- arylimidazo[1,2-a]pyridine-8-carboxylic acids in high yields. In a three component condensation reaction, isocyanide reacts with 2-aminopyridine-3-carboxylic acid and aromatic aldehydes without any prior activation. Material and Methods: The synthesized products have stable structures which have been characterized by IR, 1H, 13C and Mass spectroscopy as well as CHN-O analysis. Results: In continuation of our attempts to develop simple one-pot routes for the synthesis of 3- (cyclohexylamino)-2-arylimidazo[1,2-a]pyridine-8-carboxylic acids, aromatic aldehydes with divers substituted show a high performance. Conclusion: In conclusion, this study introduces the art of combinatorial chemistry using a simple one-pot procedure for the synthesis of new materials which are interesting compounds in medicinal and biological sciences.

Novel One-pot Synthesis of Pyranocarbazole Derivatives via an Isocyanide-based Three-component Reaction

2020 ◽  
Vol 17 ◽  
Author(s):  
Visarapu Malathi ◽  
Pedavenkatagari Narayana Reddy ◽  
Pannala Padmaja
Keyword(s):  
Efficient Method ◽  
Atom Economy ◽  
Reaction Conditions ◽  
One Pot ◽  
Catalyst Free ◽  
One Pot Synthesis ◽  
Three Component Reaction ◽  
High Yields

Abstract:: An efficient method has been developed for the synthesis of new pyrano[3,2-c] and pyrano[3,2-a]carbazole de-rivatives via a three component reaction of 4-hydroxycarbazole or 2-hydroxycarbazole, isocyanides, and dialkylacetylenedi-carboxylates. Noteworthy features of this protocol include mild reaction conditions, catalyst-free, high atom-economy and high yields.

Design, Synthesis, Antimicrobial Evaluation and Molecular Modeling Study of New 2-mercaptoimidazoles (Series-III)

2019 ◽  
Vol 16 (5) ◽  
pp. 512-521 ◽  
Author(s):  
Nidhi Rani ◽  
Randhir Singh
Keyword(s):  
Sulfonic Acid ◽  
Docking Study ◽  
Molecular Docking Study ◽  
One Pot ◽  
Design Synthesis ◽  
Toluene Sulfonic Acid ◽  
Antimicrobial Evaluation ◽  
Bacteria And Fungi ◽  
High Yields ◽  
Antimicrobial Potency

Background: A series of novel substituted 2-mercaptoimidazoles was synthesised efficiently and in high yields using one-pot synthesis from m-hydroxyacetophenones. Methods: The structures of the newly synthesized compounds were established, their molecular activity was investigated against some bacteria and fungi were further validated using molecular docking study. Results: Reaction of o-hydroxyphenacylbromide (2) with substituted aniline and KSCN, in the presence of catalyst p-toluene sulfonic acid afforded 4(a-r) in good yield. The structure of compounds (4a-r) was confirmed by IR, NMR and MS. Conclusion: The compounds exhibited excellent antimicrobial potency against the tested microorganism.

scholarly journals A New and Efficient One-pot Synthesis of Trialkyl 6-tert-Butylamino-2H-pyran-2-one-3,4,5-tricarboxylates

1999 ◽  
Vol 23 (6) ◽  
pp. 368-369
Author(s):  
Issa Yavari ◽  
Abbas Ali Esmaili ◽  
Sakineh Asghari ◽  
Hamid Reza Bijanzadeh
Keyword(s):  
One Pot ◽  
Tert Butyl ◽  
Dialkyl Acetylenedicarboxylates ◽  
One Pot Synthesis ◽  
High Yields

The highly reactive 1:1 intermediate produced in the reaction between tert-butyl isocyanide and dialkyl acetylenedicarboxylates is trapped by dialkyl 2-bromomalonates to yield the title compounds in fairly high yields.

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