10333-14-9

Usage

Uses

Used in Pharmaceutical Industry:
3,4-dihydro-6-methyl-2-pyridone is used as a building block and intermediate for the synthesis of various pharmaceuticals and organic compounds. Its versatile reactivity and potential applications in the development of new drugs and therapeutic agents make it a valuable component in this industry.

InChI:InChI=1/C6H9NO/c1-5-3-2-4-6(8)7-5/h3H,2,4H2,1H3,(H,7,8)

Upstream product

• 10412-98-3 5-oxohexanenitrile 
• 13984-50-4 methyl levulinate 
• 66156-71-6 5-oxo-hexanoic acid amide 
• 3128-06-1 5-ketohexanoic acid 
• 100556-63-6 6-Iodomethyl-piperidin-2-one 
• 28487-09-4 hex-5-enamide 
• 1577-22-6 5-hexenoic acid 
• 36394-07-7 5-hexenoyl chloride 

Downstream Products

• 66156-71-6 5-oxo-hexanoic acid amide 
• 34399-44-5 des-N-methyl-α-obscurine 
• 34399-44-5 rac-N-Desmethyl-α-obscurin 

Relevant academic research and scientific papers

One-pot synthesis of ene-lactams via N-debenzylation of keto-containing N-2,4-dimethoxylbenzylamides

A general method of ene-lactam preparation is described. Ene-lactams can be prepared efficiently from keto-containing N-2,4-dimethoxylbenzylamides in good to excellent yields. This method is applicable for the preparation of substituted δ-, γ-, and ε-ene-lactams and bicyclic ene-lactams.

Synthesis of lactams via copper-catalyzed intramolecular vinylation of amides

(Chemical Equation Presented) Copper-catalyzed intramolecular vinylation of iodoenamides were investigated for the first time. With Cul as the catalyst and N,W-dimethylethyienediamine as the ligand, a number of iodoenamides underwent cyclization in dioxane leading to the formations of five- to seven-membered lactams in moderate to excellent yields.

Bioinspired Diversification Approach Toward the Total Synthesis of Lycodine-Type Alkaloids

Nitrogen heterocycles (azacycles) are common structural motifs in numerous pharmaceuticals, agrochemicals, and natural products. Many powerful methods have been developed and continue to be advanced for the selective installation and modification of nitrogen heterocycles through C-H functionalization and C-C cleavage approaches, revealing new strategies for the synthesis of targets containing these structural entities. Here, we report the first total syntheses of the lycodine-type Lycopodium alkaloids casuarinine H, lycoplatyrine B, lycoplatyrine A, and lycopladine F as well as the total synthesis of 8,15-dihydrohuperzine A through bioinspired late-stage diversification of a readily accessible common precursor, N-desmethyl-β-obscurine. Key steps in the syntheses include oxidative C-C bond cleavage of a piperidine ring in the core structure of the obscurine intermediate and site-selective C-H borylation of a pyridine nucleus to enable cross-coupling reactions.

Total synthesis of (+)-complanadine a using an iridium-catalyzed pyridine C-H functionalization

The total synthesis of the Lycopodium alkaloid complanadine A, which is an unsymmetrical dimer of lycodine, was achieved by exploiting a common tetracyclic precursor. Key to the success of the synthesis was the development of a late-stage site-selective C-H functionalization of a pyridine moiety to arrive at a key boronic ester intermediate.

Nitrogen fixation: Synthesis of heterocycles using molecular nitrogen as a nitrogen source

Nitrogen fixation using transition metals is a fascinating process. We have already reported on the incorporation of molecular nitrogen into organic compounds using a titanium-nitrogen complex reported by Yamamoto. We developed a novel titanium-catalyzed nitrogenation procedure using TiCl4 in the presence of an excess amount of Li and TMSCl. In this reaction, a 1 atm pressure of nitrogen gas can be used and the reaction proceeds at room temperature. The procedure is very simple. A THF solution of TiCl4 or Ti(O iPr)4 (1 equiv.), Li (10 equiv.), and TMSCl (10 equiv.) was stirred under an atmosphere of nitrogen at room temperature overnight to give titanium-nitrogen complexes. Although the structures of the titanium-nitrogen complexes have not yet been determined, they would consist of N(TMS)3, X2TiN(TMS)2, and XTi=NTMS. Using this procedure, various heterocycles, such as indole, quinoline, pyrrole, pyrrolizine, and indolizine derivatives, could be synthesized from molecular nitrogen in good-to-moderate yields as a stoichiometric reaction based on a titanium complex by a one-pot reaction. Furthermore, monomorine I and pumiliotoxin C were synthesized from molecular nitrogen as a nitrogen source. This procedure was further extended for the syntheses of heterocycles using a catalytic amount of titanium complex; also, indole and pyrrole derivatives were obtained in high yields.

Ruthenium-Catalyzed Hydration of Nitriles and Transformation of δ-Ketonitriles to Ene-lactams: Total Synthesis of (-)-Pumiliotoxin C

Hydration of nitriles with 1-2 equivalents of water can be performed efficiently by using RuH2(PPh3)4 catalyst to give the corresponding amides.Under the similar reaction conditions, δ-ketonitriles can be converted into the corresponding ene-lactams, which are versatile synthetic intermediates.The efficiency of the reaction is demonstrated by the short-step synthesis of (-)-pumiliotoxin C.

Synthesis and Reactions of Iodo Lactams

The synthesis of a series of iodo lactams has been achieved by a new cyclization method that depends on generating N,O-bis(trimethylsilyl)imidate derivatives as intermediates.Treatment of an unsaturated amide with trimethylsilyl triflate in pentane and then iodine in tetrahydrofuran gives the iodo lactam.Some reactions of this new difunctional group with bases, nucleophiles, and Michael acceptors leading to functionalized or elaborated lactams are presented.In general, iodo lactams undergo direct SN2 reactions with reactive (but weakly basic) nucleophiles like azide and triphenylphosphine and elimination or decomposition in the presence of bases or basic nucleophiles.Sodium hydride may be used to generate an N-acylaziridine intermediate, which can be opened with azide to deliver an azido lactam with overall retention of stereochemistry.Silver-assisted solvolysis of iodo lactams gives the hydroxy lactams with retention of configuration, probably also because of participation by the lactam nitrogen.The sodium salt of 5-(iodomethyl)-2-pyrrolidinone (3), generated at -20 deg C, undergoes an annulation reaction with unsaturated esters (but not sulfones), leading to pyrrolizidine derivatives.

STEREOCONTROLLED SYNTHESIS OF DIAMINES FROM IODOLACTAMS

Displacement of iodide from iodolactams by azide occurs with retention of configuration if a catalytic amount of NaH is added, due to the intervention of an N-acyl-aziridine.Several diamine equivalents and a spermidine analogue are prepared in this way.

Synthesis of the Lycopodium Alkaloid rac-α-Obscurine by 1,3-Annulation of an Enimine

Acid catalysed 1,3-annulation of 1,2,3,4-tetrahydro-6-methyl-2-oxopyridine (1) to the enimine 3, followed by methylation, provides a new regio and stereoselective route to rac-α-obscurine (5).Reduction of rac-N-desmethyl-α-obscurine with LiAlH4 yields rac-lycodine (11) and rac-deacetylflabellidine (9).A new pathway for the biogenesis of the β-amino-imine 9 is suggested.