Browse
Submit Data
Databases
API
Help

Dataset Information

25 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

One-pot four-component synthesis of pyrimidyl and pyrazolyl substituted azulenes by glyoxylation-decarbonylative alkynylation-cyclocondensation sequences.

ABSTRACT: A novel one-pot four-component synthesis of pyrimidyl- and pyrazolylazulenes through the use of glyoxylation-decarbonylative alkynylation-cyclocondensation sequences starting from azulene or guaiazulene as substrates, gives rise to the formation of the target compounds in moderate to good yields.

SUBMITTER: Gers CF

PROVIDER: S-EPMC3168959 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

One-pot activation-alkynylation-cyclization synthesis of 1,5-diacyl-5-hydroxypyrazolines in a consecutive three-component fashion.

Project description:A consecutive three-component activation-alkynylation-cyclization reaction of (hetero)aryl glyoxylic acids, oxalyl chloride, arylacetylenes, and hydrazides efficiently forms 1,5-diacyl-5-hydroxypyrazolines in moderate to good yields. The structures were unambiguously corroborated by comprehensive NMR spectroscopy and X-ray structure analyses of selected derivatives.

| S-EPMC6604727 | biostudies-literature

Regioselective, one-pot, multi-component, green synthesis of substituted benzo[<i>c</i>]pyrazolo[2,7]naphthyridines.

Project description:An efficient and environmentally benign synthetic protocol has been developed for the synthesis of benzo[c]pyrazolo[2,7]naphthyridine derivatives through regioselective multi-component "on-water" reaction of isatin, malononitrile and 3-aminopyrazole. The Knoevenagel condensation of isatin with malononitrile resulted in the formation of arylidene, which subsequently underwent Michael addition with 3-aminopyrazole followed by basic hydrolysis, cyclization, decarboxylation and aromatization to give the target naphthyridines in good to excellent yields. The one-pot multi-component protocol was also employed to obtain the said naphthyridines in a lower yield (10-15%) than obtained by basic hydrolysis of spiro-intermediates. The present study shows attractive features such as the use of water as a green solvent, short reaction time, reduced waste products and transition metal free C-C and C-N bond formation. The structures of the synthesized derivatives were established through FTIR, 1H-NMR, 13C-NMR spectroscopy and ESI-mass spectrometry.

| S-EPMC9049208 | biostudies-literature

One-pot four-component reaction for convenient synthesis of functionalized 1-benzamidospiro[indoline-3,4'-pyridines].

Project description:The one-pot four-component reaction of benzohydrazide (2-picolinohydrazide), acetylenedicarboxylate, isatins and malononitrile (ethyl cyanoacetate) with triethylamine as base catalyst afforded functionalized 1-benzamidospiro[indoline-3,4'-pyridines] in good yields. (1)H NMR spectra indicated that an equilibrium of cis/trans-conformations exist in the obtained products.

| S-EPMC4273213 | biostudies-literature

A convenient four-component one-pot strategy toward the synthesis of pyrazolo[3,4-d]pyrimidines.

Project description:An efficient one-pot synthesis of pyrazolo[3,4-d]pyrimidine derivatives by the four-component condensation of hydrazines, methylenemalononitriles, aldehydes and alcohols has been developed via two different reaction pathways. The structures of target products were characterized by IR spectroscopy, NMR ((1)H and (13)C) spectroscopy and HRMS (ESI) spectrometry. The crystal structure of 4-ethoxy-6-(2-nitrophenyl)-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine was determined by single crystal X-ray diffraction.

| S-EPMC4660965 | biostudies-literature

One-pot, sequential four-component synthesis of novel heterocyclic [3.3.3] propellane derivatives at room temperature.

Project description:An efficient, one-pot, two-step, four-component reaction for the synthesis of propellane derivatives is described by the condensation reaction between acenaphthenequinone, malono derivatives, primary amines and β-ketoester or β-diketone derivatives in the presence of triethylamine in ethanol at room temperature. Using this procedure, all the products were obtained in good to excellent yields.

| S-EPMC9079859 | biostudies-literature

One-pot three component synthesis of substituted dihydropyrimidinones using fruit juices as biocatalyst and their biological studies.

Project description:New and facile one-pot three component approach for the synthesis of substituted dihydropyrimidinones derivatives (4a-4h) from reaction of equimolar substituted aldehydes (1a-1h), methyl acetoacetate (2a) and urea (3a) in presence of nature derived catalyst viz. Cocos nucifera L. juice, Solanum lycopersicum L. juice and Citrus limetta juice, commonly known as coconut juice, tomato juice and musambi juice respectively, at room temperature has been carried out. All synthesized compounds were evaluated for in vitro herbicidal activity against Raphanus sativus L. (Radish seeds). The compounds (4a-4h) were also screened for their antifungal activity against Rhizoctonia solani and Colletotrichum gloeosporioides by poisoned food techniques method. Antibacterial activity was also studied against Erwinia cartovora and Xanthomonas citri by inhibition zone method. From activity data, it was found that compounds 4g and 4d were most active against Raphanus sativus L. (root) and Raphanus sativus L. (shoot) respectively. Compounds 4f and 4c was found most active against Rhizoctonia solani and Colletotrichum gloeosporioides fungus respectively at highest concentration. Compound 4g has shown maximum inhibition zone i.e. 1.00-5.50 mm against Erwinia cartovora at 2000 μg/mL concentration. Maximum Xanthomonas citrii growth was inhibited by compounds 4f showing inhibition zone 4.00-12.00 mm at highest concentration. Short reaction time, high yields, mild reaction condition and simple work-up are some merits of present methodology.

| S-EPMC7491738 | biostudies-literature

Synthesis of a library of "lead-like" ?-lactams by a one pot, four-component reaction.

Project description:The synthesis of a pilot scale library of 116 structurally diverse ?-lactams is reported. The library core structure emanates from a ?-lactam forming one-pot, four-component reaction of ammonium acetate, p-methoxythiophenol, p-methoxybenzaldehyde, and maleic anhydride. Structural diversity then arises from amide coupling, thioaryl cleavage, N-functionalization, and heterocycle forming reactions on this core structure. Computational analysis reveals that the library contains molecular properties and shape diversity suitable for drug lead and biological probe discovery.

| S-EPMC3816122 | biostudies-other

Facile one-pot four-component synthesis of 3,4-dihydro-2-pyridone derivatives: novel urease inhibitor scaffold.

Project description:In the current study, a series of 3,4-dihydro-2-pyridone derivatives were synthesized in a one-pot fourcomponent reaction of Meldrum's acid, benzaldehyde derivatives, methyl acetoacetate, and ammonium acetate. SiO2-Pr-SO3H was used as an efficient catalyst for the synthesis of the target compounds under solvent-free conditions. The most probable mechanism for this reaction has been discussed. The advantages of this methodology are high product yields, being environmentally benign, short reaction times, and easy handling. Eight 2-pyridinone derivatives were evaluated for their inhibitory activities against Jack bean urease. Molecular docking study of the synthesized compounds was also evaluated. All compounds showed good activities against urease and among them, 4-(4-nitrophenyl)-5-methoxycarbonyl-6-methyl-3,4-dihydropyridone (5a) showed the most potent activity (IC50 = 29.12 µM), more potent than hydroxyurea as the reference drug (IC50 = 100.0 µM). Also, the results from docking studies were in good agreement with those obtained with in vitro assay. According to the docking studies methionine (Met) 637 and nitro phenyl ring cause n-π interaction between lone pair of sulfur atom and π aromatic ring. Moreover, hydrophobic interactions existed between compound 5a and alanine (ALA) 636, ALA 440, and isoleucine 411. The results indicated that the inhibitory activities increased with the increase of electron withdrawing ability of the groups despite a less important role of lipophilicity in increasing the inhibitory activity.

| S-EPMC5615865 | biostudies-literature

Synthesis of functionalized spiro[indoline-3,4'-pyridines] and spiro[indoline-3,4'-pyridinones] via one-pot four-component reactions.

Project description:In the presence of triethylamine as catalyst, the one-pot four-component reactions of arylamines, methyl propiolate, isatin and malononitrile afforded the functionalized spiro[indoline-3,4'-pyridine] derivatives in good yields. Similar reactions with ethyl cyanoacetate successfully afforded the functionalized spiro[indoline-3,4'-pyridines] and spiro[indoline-3,4'-pyridinones] as the main products according to the structures of the arylamines and other primary amines.

| S-EPMC3678513 | biostudies-literature

Catalytic enantioselective reductive alkynylation of amides enables one-pot syntheses of pyrrolidine, piperidine and indolizidine alkaloids.

Project description:The primary objective in synthetic organic chemistry is to develop highly efficient, selective, and versatile synthetic methodologies, which are essential for discovering new drug candidates and agrochemicals. In this study, we present a unified strategy for a one-pot, catalytic enantioselective synthesis of α-alkyl and α,α'-dialkyl pyrrolidine, piperidine, and indolizidine alkaloids using readily available amides and alkynes. This synthesis is enabled by the identification and development of an Ir/Cu/N-PINAP catalyzed highly enantioselective and chemoselective reductive alkynylation of α-unbranched aliphatic amides, which serves as the key reaction. This reaction is combined with Pd-catalyzed tandem reactions in a one-pot approach, enabling the collective, catalytic enantioselective total syntheses of eight alkaloids and an anticancer antipode with 90-98% ee. The methodology's enantio-divergence is exemplified by the one-step access to either enantiomer of alkaloid bgugaine.

| S-EPMC10558451 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data