One-pot three-component route for the synthesis of S-trifluoromethyl dithiocarbamates using Togni’s reagent

A one-pot three-component route for the synthesis of S-trifluoromethyl dithiocarbamates by the reaction of secondary amines, carbon disulfide and Togni’s reagent is described. The reactions proceed in moderate to good yields. A similar reaction using a primary aliphatic amine afforded the corresponding isothiocyanate in high yield. A variable temperature NMR study revealed a rotational barrier of 14.6, 18.8, and 15.9 kcal/mol for the C–N bond in the dithiocarbamate moiety of piperidine, pyrrolidine, and diethylamine adducts, respectively. In addition, the calculated barriers of rotation are in reasonable agreement with the experiments.

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Flow synthesis of secondary amines over Ag/Al2O3 catalyst by one-pot reductive amination of aldehydes with nitroarenes

RSC Advances ◽

10.1039/c7ra08986d ◽

2017 ◽

Vol 7 (72) ◽

pp. 45856-45861 ◽

Cited By ~ 9

Author(s):

Ekaterina A. Artiukha ◽

Alexey L. Nuzhdin ◽

Galina A. Bukhtiyarova ◽

Valerii I. Bukhtiyarov

Keyword(s):

Reductive Amination ◽

Flow Reactor ◽

Secondary Amines ◽

High Yield ◽

One Pot ◽

Flow Synthesis ◽

Al2o3 Catalyst

The reaction of aldehydes with nitroarenes over Ag/Al2O3 catalyst under H2 in a flow reactor gives secondary amines in high yield.

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Practical Synthesis of 2'-5'-Linked Oligoadenylates (2-5A Oligomers)

Australian Journal of Chemistry ◽

10.1071/ch9920205 ◽

1992 ◽

Vol 45 (1) ◽

pp. 205 ◽

Cited By ~ 8

Author(s):

R Noyori ◽

M Uchiyama ◽

T Nobori ◽

M Hirose ◽

Y Hayakawa

Keyword(s):

Ethyl Acetate ◽

Second Order ◽

High Yield ◽

Similar Reaction ◽

Reaction Sequence ◽

Facile Synthesis ◽

One Pot ◽

Subsequent Oxidation ◽

Practical Synthesis ◽

Related Compounds

A general, facile synthesis of 2'-5'-linked oligonucleotides (2-5A oligomers ) has been achieved based on the second-order regioselective protection of adenosine, one-pot formation of the 2'5' internucleotide linkage, and O-selective phosphorylation of N-unblocked nucleosides. Standard t- butyldimethylsilylation of 5'-O-p-methoxytrityladenosine followed by careful recrystallization from a mixture of triethylamine , methanol, ethyl acetate and ether (4 : 4 : 5 : 100 v/v) gives the 3',5'-di-O-protected adenosine in high yield. Magnesium alkoxide -mediated condensation of the 2'-O-free adenosine with o-chlorophenyl p-nitrophenyl phosphorochloridate followed by 2',3'-di-O-t-butyldimethylsilyladenosine produces the N-free and fully O-protected adenylyl (2'-5')adenosine. The resulting adenylyl dimer, after removal of the 5'-O-trityl protector, is elongated to the protected trimeric compound through a similar reaction sequence. Deprotection of the product furnishes the 2-5A core. Condensation of the 5?-0-detritylated core and bis (2,2,2-trichloroethyl) phosphorochloridite assisted by 2,6-lutidine and subsequent oxidation with aqueous iodine produces, after deblocking, 2-5A 5'-monophosphate (p5'A2'p5'pA2'p5'A). The 2-5A 5'-monophosphate is converted into 2-5A 5'-triphosphate (ppp5'A2'p5'A2'p5'A) by reaction with N,N'-carbonyldiimidazole in the presence of triethylamine followed by tributylammonium diphosphate. This procedure allows ready synthesis of 2-5A oligomers and related compounds on a multigram scale.

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Electrochemical Synthesis of Allylic Amines from Alkenes and Amines

10.33774/chemrxiv-2021-11hm2 ◽

2021 ◽

Author(s):

Diana Wang ◽

Karina Targos ◽

Zachary Wickens

Keyword(s):

Aliphatic Amine ◽

Reactive Intermediates ◽

Building Blocks ◽

Electrochemical Process ◽

Biologically Active ◽

Secondary Amines ◽

High Yield ◽

Mechanistic Studies ◽

Allylic Amines ◽

Synthetic Strategy

Allylic amines are valuable synthetic targets en route to diverse biologically active amine products. Current allylic C–H amination strate-gies remain limited with respect to the viable N-substituents. Herein we disclose a new electrochemical process to prepare aliphatic allylic amines by coupling two abundant starting materials: secondary amines and unactivated alkenes. This oxidative transformation proceeds via electrochemical generation of an electrophilic adduct between thianthrene and the alkene substrates. Treatment of these adducts with aliphatic amine nucleophiles and base provides allylic amine products in high yield. This synthetic strategy is also amenable to functionali-zation of feedstock gaseous alkenes at 1 atmosphere. In the case of 1-butene, remarkable Z-selective crotylation is observed. This strategy, however, is not limited to the synthesis of simple building blocks; complex biologically active molecules are suitable as both alkene and amine coupling partners. Preliminary mechanistic studies implicate vinylthianthrenium salts as key reactive intermediates.

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One-pot Synthesis and Dynamic Studies of Stable Dialkyl-2-(1H-Isoindol-1,3(2H)-dione-2-yl)-3-(Triphenylphosphoranylidene) Butanedioate ylides

Journal of Chemical Research ◽

10.3184/030823401103169478 ◽

2001 ◽

Vol 2001 (5) ◽

pp. 192-194 ◽

Cited By ~ 8

Author(s):

Ahmad Shaabani ◽

Hamid Reza Safaei ◽

Kiana Hemyari ◽

Abolghasem Moghimi

Keyword(s):

Nucleophilic Addition ◽

High Yield ◽

Dynamic Nmr ◽

Phosphonium Salts ◽

One Pot ◽

Dialkyl Acetylenedicarboxylate ◽

One Pot Synthesis ◽

Dynamic Studies ◽

Nmr Study

The title compounds were prepared in high yield by protonation of the reactive 1:1 intermediates produced in the reaction between triphenylphosphine and dialkyl acetylenedicarboxylate by phthalimide, followed by nucleophilic addition of the imidic nitrogen anion to the vinyl phosphonium salts. A dynamic NMR study was also performed.

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Synthesis of Highly Functionalized Quinazoline-2,4(1H,3H)-diones from Isocyanides, Aniline and Isocyanate via Cu-Catalyzed Intermolecular C-H Activation Reactions

Letters in Organic Chemistry ◽

10.2174/1570178616666190905142545 ◽

2020 ◽

Vol 17 (11) ◽

pp. 832-836

Author(s):

Manijeh Nematpour ◽

Hossein Fasihi Dastjerdi ◽

Mehdi Jahani ◽

Sayyed Abbas Tabatabai

Keyword(s):

13C Nmr ◽

Reaction Times ◽

High Yield ◽

One Pot ◽

1H And 13C Nmr ◽

Activation Reaction ◽

Elemental Analyses

A simple and appropriate procedure for the synthesis of quinazoline-2,4(1H,3H)-dione derivatives from isocyanides, aniline and isocyanate via the Cu-catalyzed intramolecular C-H activation reaction is reported. The advantages of this method are one-pot conditions, accessible starting materials- catalyst, high yield of products, and short reaction times. The structures are confirmed spectroscopically (1H- and 13C-NMR, IR and EI-MS) and by elemental analyses.

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Design, Synthesis, In vitro Cytotoxic Activity Evaluation, and Study of Apoptosis Inducing Effect of New Styrylimidazo[1,2-a]Pyridines as Potent Anti-Breast Cancer Agents

Anti-Cancer Agents in Medicinal Chemistry ◽

10.2174/1871520618666180903100835 ◽

2019 ◽

Vol 19 (2) ◽

pp. 265-275 ◽

Cited By ~ 2

Author(s):

Faeze Khalili ◽

Sara Akrami ◽

Malihe Safavi ◽

Maryam Mohammadi-Khanaposhtani ◽

Mina Saeedi ◽

...

Keyword(s):

Breast Cancer ◽

Cytotoxic Activity ◽

High Yield ◽

Breast Cancer Cell Lines ◽

Pyridine Derivatives ◽

One Pot ◽

Standard Drug ◽

Three Component Reaction ◽

Anti Cancer

Background: This paper reports synthesis, cytotoxic activity, and apoptosis inducing effect of a novel series of styrylimidazo[1,2-a]pyridine derivatives. Objective: In this study, anti-cancer activity of novel styrylimidazo[1,2-a]pyridines was evaluated. Methods: Styrylimidazo[1,2-a]pyridine derivatives 4a-o were synthesized through a one-pot three-component reaction of 2-aminopyridines, cinnamaldehydes, and isocyanides in high yield. All synthesized compounds 4a-o were evaluated against breast cancer cell lines including MDA-MB-231, MCF-7, and T-47D using MTT assay. Apoptosis was evaluated by acridine orange/ethidium bromide staining, cell cycle analysis, and TUNEL assay as the mechanism of cell death. Results: Most of the synthesized compounds exhibited more potent cytotoxicity than standard drug, etoposide. Induction of apoptosis by the most cytotoxic compounds 4f, 4g, 4j, 4n, and 4m was confirmed through mentioned methods. Conclusion: In conclusion, these results confirmed the potency of styrylimidazo[1,2-a]pyridines for further drug discovery developments in the field of anti-cancer agents.

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