149221-40-9

Upstream product

• 3859-41-4 1,3-cyclopentadione 
• 100-46-9 benzylamine 
• 5870-62-2 3-hydroxy-2-cyclopenten-1-one 
• 930-30-3 cyclopent-2-enone 
• 622-79-7 benzyl azide 
• 205999-79-7 3-oxocyclopent-1-en-1-yl 4-methylbenzenesulfonate 

Downstream Products

• 183674-21-7 N-benzyl-N-(3-oxocyclopent-1-enyl)pent-4-enamide 
• 28566-12-3 3-amino-cyclopent-2-en-1-one 
• 1402907-02-1 1-benzyl-1,2,6,7-tetrahydro-2-methyl-2-(4-methylpent-3-enyl)-5H-cyclopenta[b]pyridin-5-one 
• 1402907-01-0 1-benzyl-1,2,6,7-tetrahydro-2,2-dimethyl-5H-cyclopenta[b]pyridin-5-one 

Relevant academic research and scientific papers

Lewis Acid-Mediated Reactions of Alkyl Azides with α,β- Unsaturated Ketones

(Matrix presented) Alkyl azides react with saturated ketones upon treatment with Lewis acids to afford ring-expansion products through the azido-Schmidt reaction, but this reaction does not proceed when α,β-unsaturated ketones are used. In this study, alk

A four-component domino reaction: An eco-compatible and highly efficient construction of 1,8-naphthyridine derivatives, their in silico molecular docking, drug likeness, ADME, and toxicity studies

A multicomponent domino reaction of enaminone, malononitrile, and o-phthalaldehyde has been established, providing direct access to novel highly functionalized pentacyclic cyclopenta [b] indeno [1, 2, 3-de] [1,8] naphthyridine derivatives. The simplicity of execution, readily available substrates, high yields, excellent functional group tolerance, scalability, and good scores of environmental parameters make this synthetic strategy more sustainable and worthy of further attention. This one-pot transformation, which involved multiple steps and did not require the use of a catalyst, constructed four new C-C bonds, two new C-N bonds, and three new rings, with efficient use of all reactants. Furthermore, we performed in silico molecular docking analysis for prediction of anticancer (against human topoisomerase IIβ protein) and antimicrobial (against E.coli. DNA gyrase B protein) activities. Drug likeness and ADMET studies were also predicted. Overall investigation indicates that compound 6i may serve as a candidate that could be developed as potential anticancer and antimicrobial agent among all.

Synthesis of β-triazolylenones via metal-free desulfonylative alkylation of N-tosyl-1,2,3-triazoles

Desulfonylative alkylation of N-tosyl-1,2,3-triazoles under metal-free conditions leading to β-triazolylenones is reported here. The present study encompasses the synthesis of triazoles with a new substitution pattern in a single step from cyclic 1,3-dicarbonyl compounds and N-tosyl triazole in moderate to high yields. Our synthesis takes place with complete regioselectivity as confirmed by crystallographic analysis which is rationalized by a suitable mechanistic proposal. This method provides an efficient, versatile and straightforward strategy towards the synthesis of new functionalized 1,2,3-triazoles.

Redox Property of Enamines

Enamines are electron-rich compounds bearing intriguing redox properties. Herein, a series of secondary enamines condensed from primary amine and β-ketocarbonyls were synthesized and their electrochemical oxidation properties were systematically studied by cyclic voltammetry. Furthermore, theoretical calculation of oxidation potentials of enamines, particularly those catalytic intermediates, was also conducted to further broaden the scope investigated. Possible structural factors on oxidation and the nature of the resulted radical cation intermediates were revealed and discussed. Correlation of redox potentials with molecular properties such as highest occupied molecular orbital energies and natural population analysis charge were explored, and there appears no simple linear correlation. On the other hand, a good correlation with Mayr's nucleophilicity parameter N was noted among a range of catalytically relevant enamines. Spin population analysis disclosed that enamine radical cations mainly exhibit the carbon-center free radical feature. Taking experimental and computation data together, a comprehensive picture about the redox property of enamines is presented, which would provide guidance in the development of oxidative enamine catalysis and transformations.

Cu catalyzed cross-dehydrogenative coupling reaction for the synthesis of 3-hydroxy-2-pyrrolidinones

A new convenient strategy for the synthesis of 3-hydroxy-2-pyrrolidinone derivatives featuring regioselective C–C coupling has been developed. This is a Cu (II) catalyzed cross dehydrogenative coupling (CDC) involving enamino-ketones of benzyl amines and di-alkyl acetylenedicarboxylate, followed by cyclization by primary amines. TBHP (tert-butyl hydroperoxide) has been used as the oxidant to promote the coupling protocol. This synthetic route principally demonstrates the scope of CDC reaction and also applicable to gram-scale synthesis.

Vanadium(IV) acetylacetonate catalyzed stereoselective synthesis of β-enaminoesters and β-enaminones

An efficient and stereoselective procedure has been described for the synthesis of a series of β-enaminoesters and β-enaminones by vanadium(IV) acetylacetonate [VO(acac)2] catalyzed reaction of β-ketoesters and 1,3-diketones with both aliphatic and aromatic amines. X-ray crystallographic studies of some representative compounds corroborate two types of structural geometry formed by inter-molecular as well as intra-molecular hydrogen bonds.

Efficient synthesis of tetrahydroquinolinones by acetic acid-mediated formal [3+3] cycloaddition

A simple and efficient method to synthesize a variety of tetrahydroquinolinones was successfully achieved by reacting various β-enaminones with several α,β-unsaturated aldehydes. This strategy can be viewed as a Bronsted acid-mediated formal [3+3] cycloaddition. Springer-Verlag 2012.

Intramolecular [2 + 2] photocvcloaddition of N-alkenovl-β-enaminones

The photolysis of cyclic N-alkenoyl β-enaminones is described. In general, a very regio- and stereoselective intramolecular [2 + 2] photocydoaddition was observed. The limitations of the reaction process are discussed. The main competitive reaction, which

Synthesis and Anticonvulsant Activity of Enaminone. 2. Further Structure-Activity Correlations.

This report continues the in-depth evaluation of methyl 4--6-methyl-2-oxocyclohex-3-en-1-oate, 1 (ADD 196022), and methyl 4-(benzylamino)-6-methyl-2-oxocyclohex-3-en-1-oate, 2, two potent anticonvulsant enaminones.These compounds were evaluated employing the amygdala kindling model.Neither 1 nor 2 was active against amygdala kindled seizures, further supporting the corneal kindled model as a definitive tool for antielectroshock seizure evaluation as previously reported.Additional intraperitoneal (ip) data on 1 revealed toxicity at 24 h at 100 mg/kg.Several active analogs have been prepared with the view to minimizing toxicity.In a special ip rat screen developed by the Antiepileptic Drug Development (ADD) Program, these newer analogs were evaluated for protection against maximal electroshock seizures (MES) at 10 mg/kg and neurotoxicity at 100 mg/kg.From this screen, several compounds were shown to be safer alternatives, the most notable was methyl 4--6-methyl-2-oxocyclohex-3-en-1-oate, 13.Compound 13 had an ip ED50 of 4 mg/kg in the rat and a TD50 of 269 mg/kg, providing a protective index (TD50/ED50) of > 67.By variation in the ring size, additional aromatic substitutions and the synthesis of acyclic analogs, these newer compounds provide a more definitive insight into the structure-activity correlation.CLOGP evaluation and molecular modeling studies are also provided to further elaborate the molecular characteristics of potential anticonvulsant enaminones.