scholarly journals Alkoxide-induced ring opening of bicyclic 2-vinylcyclobutanones: A convenient synthesis of 2-vinyl-substituted 3-cycloalkene-1-carboxylic acid esters

2012 ◽  
Vol 8 ◽  
pp. 650-657 ◽  
Author(s):  
Xiufang Ji ◽  
Zhiming Li ◽  
Quanrui Wang ◽  
Andreas Goeke
Keyword(s):  
Carboxylic Acid ◽  
Ring Opening ◽  
Claisen Rearrangement ◽  
Ring Cleavage ◽  
Unsaturated Ester ◽  
Supplementary Method ◽  
Convenient Synthesis ◽  
High Yields ◽  
Acid Esters

The fused 2-vinyl or 2-phenyl substituted cyclobutanones 4 undergo stereoselective ring openings by the action of alkoxide ions (t-BuO− or MeO−) to produce novel vicinally disubstituted cycloalkene derivatives 5 and 6 in moderate to high yields. The ring cleavage usually occurs with complete regioselectivity. The accessibility of γ,δ-unsaturated ester or acid derivatives makes this transformation a good supplementary method for the well-established Johnson–Claisen rearrangement.

scholarly journals A CONVENIENT SYNTHESIS AND CYTOTOXIC ACTIVITY OF 3-ARYL-5-PENTYL-1,2,4-OXADIAZOLES FROM CARBOXYLIC ACID ESTERS AND ARYLAMIDOXIMES UNDER SOLVENT-FREE CONDITIONS

2014 ◽  
Vol 59 (1) ◽  
pp. 2359-2362 ◽  
Author(s):  
CARLOS JONNATAN PIMENTEL BARROS ◽  
ZILYANE CARDOSO DE SOUZA ◽  
JUCLEITON JOSÉRUFINO DE FREITAS ◽  
PAULO BRUNO NORBERTO DA SILVA ◽  
GARDENIA CARMEN GADELHA MILITÃO ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Cytotoxic Activity ◽  
Solvent Free ◽  
Convenient Synthesis ◽  
Solvent Free Conditions ◽  
Acid Esters

The Reaction of Carboxylic Acid Esters with RfMgBr: A Convenient Synthesis of Perfluoroalkyl Ketones

2010 ◽  
Vol 2010 (36) ◽  
pp. 7012-7019 ◽  
Author(s):  
Can Xue ◽  
Guangke He ◽  
Chunling Fu ◽  
Liqin Xue ◽  
Zhenyang Lin ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Convenient Synthesis ◽  
Acid Esters

ChemInform Abstract: The Reaction of Carboxylic Acid Esters with RfMgBr: A Convenient Synthesis of Perfluoroalkyl Ketones.

ChemInform ◽  
2011 ◽  
Vol 42 (18) ◽  
pp. no-no
Author(s):  
Can Xue ◽  
Guangke He ◽  
Chunling Fu ◽  
Liqin Xue ◽  
Zhengyan Lin ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Convenient Synthesis ◽  
Acid Esters

Ring Opening of Dihydro-1,4-oxathiins

1973 ◽  
Vol 51 (16) ◽  
pp. 2650-2658 ◽  
Author(s):  
Maurice Armand Corbeil ◽  
Michael Curcumelli-Rodostamo ◽  
Robert James Fanning ◽  
Bruce Allan Graham ◽  
Marshall Kulka ◽  
...  
Keyword(s):  
Carboxylic Acid ◽  
Acid Hydrolysis ◽  
Ring Opening ◽  
Acid Hydrazide ◽  
Ring Cleavage ◽  
Carboxylic Acid Hydrazide ◽  
Carbonyl Chloride ◽  
Hydrolysis Of

Acid hydrolysis of 5,6-dihydro-2-methyl-1,4-oxathiin-3-carboxanilide gives 2-(2-hydroxyethylthio)-acetoacetanilide enol. 3-Carbonyl-substituted 5,6-dihydro-1,4-oxathiins were found to undergo ring cleavage by nucleophilic nitrogen attack on C-2. Thus the following reactions were observed: 3-acetyl-5,6-dihydro-2-methyl-1,4-oxathiin on treatment with hydrazine gives 4-(2-hydroxyethylthio)-3,5-di-methylpyrazole, instead of the hydrazone. The 1,4-oxathiins, N-(5,6-dihydro-2-methyl-1,4-oxathiin-3-ylcarbonyl)-N′-phenylurea and 5,6-dihydro-2-methyl-1,4-oxathiin-3-carboxylic acid hydrazide rearrange to give 5-(2-hydroxyethylthio)-6-methyl-1-phenyluracil and 4-(2-hydroxyethylthio)-3-methyl-2-pyrazolin-5-one, respectively. Finally, treatment of 5,6-dihydro-2-methyl-1,4-oxathiin-3-carbonyl chloride with 2-aminopyridine and with 2-aminopyrimidine affords 4H-3-(2-hydroxyethylthio)-2-methyl-pyrido[1,2-a]pyrimidin-4-one and 4H-3-(2-hydroxyethylthio)-2-methylpyrimido[1,2-a]pyrimidin-4-one, respectively, as the predominant products.

scholarly journals A Convenient Synthesis and Antibacterial Activity of Novel α-Aminophosphonic Acid Esters from Amino Acids/Esters (Kabachnik-Fields Reaction)

2008 ◽  
Vol 5 (4) ◽  
pp. 679-687 ◽  
Author(s):  
CH. Mohan ◽  
B. Hari Babu ◽  
C. Naga Raju ◽  
R. Usha Nagalakshmi
Keyword(s):  
Amino Acids ◽  
Antibacterial Activity ◽  
Aromatic Aldehydes ◽  
Aminophosphonic Acid ◽  
One Pot ◽  
Mass Spectral ◽  
Convenient Synthesis ◽  
Three Component Reaction ◽  
High Yields ◽  
Acid Esters

Synthesis of novel α-aminophosphonic acid esters (5a-n) were achieved with high yields through one-pot three component reaction process by Kabachnik-Fields reaction. It involves the reaction among amino acids/esters, substituted aromatic aldehydes and dialkyl phosphites in absolute ethanol at reflux temperature. Their structures were established by elemental analysis IR,¹H,¹³C,³¹P NMR and mass spectral data. All the title compounds were screened for their antibacterial activity. Most of the compounds exhibited moderate antimicrobial activity.

Stereospecific, Palladium-catalyzed C(sp3)–H Alkenylation and Alkynylation of a Proline Derivative Enabled by 8-Aminoquinoline as a Directing Group

2020 ◽  
Author(s):  
Aleksandra Balliu ◽  
Aaltje Roelofje Femmigje Strijker ◽  
Michael Oschmann ◽  
Monireh Pourghasemi Lati ◽  
Oscar Verho
Keyword(s):  
Carboxylic Acid ◽  
Building Blocks ◽  
Wide Range ◽  
Palladium Catalyzed ◽  
Directing Group ◽  
High Yields ◽  
Vinyl Iodides ◽  
Initial Results

<p>In this preprint, we present our initial results concerning a stereospecific Pd-catalyzed protocol for the C3 alkenylation and alkynylation of a proline derivative carrying the well utilized 8‑aminoquinoline directing group. Efficient C–H alkenylation was achieved with a wide range of vinyl iodides bearing different aliphatic, aromatic and heteroaromatic substituents, to furnish the corresponding C3 alkenylated products in good to high yields. In addition, we were able show that this protocol can also be used to install an alkynyl group into the pyrrolidine scaffold, when a TIPS-protected alkynyl bromide was used as the reaction partner. Furthermore, two different methods for the removal of the 8-aminoquinoline auxiliary are reported, which can enable access to both <i>cis</i>- and <i>trans</i>-configured carboxylic acid building blocks from the C–H alkenylation products.</p>

Ketones from Nickel-Catalyzed Decarboxylative, Non-Symmetric Cross-Electrophile Coupling of Carboxylic Acid Esters

2019 ◽  
Author(s):  
Jiang Wang ◽  
Brian P. Cary ◽  
Peyton Beyer ◽  
Samuel H. Gellman ◽  
Daniel Weix
Keyword(s):  
Carboxylic Acid ◽  
Solid Support ◽  
Reaction Conditions ◽  
Decarboxylative Coupling ◽  
New Strategy ◽  
The Cross ◽  
Acyl Donors ◽  
Acid Esters

A new strategy for the synthesis of ketones is presented based upon the decarboxylative coupling of N-hydroxyphthalimide (NHP) esters with S-2-pyridyl thioesters. The reactions are selective for the cross-coupled product because NHP esters act as radical donors and the thioesters act as acyl donors. The reaction conditions are general and mild, with over 40 examples presented, including larger fragments and the 20-mer peptide Exendin(9-39) on solid support.

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.

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