25314-92-5

Upstream product

• 127391-37-1 2-((Z)-4-Phenyl-but-1-en-3-ynyl)-pyridine 1-oxide 
• 98-88-4 benzoyl chloride 
• 32896-98-3 2-methyl-1-(2-oxo-2-phenylethyl)pyridinium bromide 
• 36805-97-7 N,N-dimethylformamide di-tert-butyl acetal 
• 136714-42-6 1-Phenacyl-α-picolinium 
• 2579-22-8 Phenylpropargyl aldehyde 
• 17881-80-0 (2-picolyl)trimethylsilane 
• 92497-49-9 2-(4-phenyl-but-1-en-3-ynyl)-pyridine 
• 108-31-6 maleic anhydride 
• 16883-69-5 N-phenacylpyridinium bromide 
• 5535-48-8 PVS 
• 110-86-1 pyridine 
• 70-11-1 α-bromoacetophenone 

Relevant academic research and scientific papers

Application of DMF-methyl sulfate adduct in the regioselective synthesis of 3-acylated indolizines

A number of 3-acylated indolizines were synthesized in good to excellent yields by a newly established reaction between picolinium salts and the methylsulfate salt of A (R = Me), the adduct formed from DMF-Me2SO4 as the key reagent.

Transition-Metal-Free Synthesis of Indolizines from Electron-Deficient Alkenes via One-Pot Reaction Using TEMPO as an Oxidant

A one-pot method for the synthesis of multisubstituted indolizines from α-halo carbonyl compounds, pyridines, and electron-deficient alkenes is reported. The oxidative dehydrogenation reaction takes place under transition-metal-free conditions using TEMPO as an oxidant. This protocol uses ready available starting materials in a convenient procedure under mild reaction conditions.

Electrophilicities of 1,2-disubstituted ethylenes

The kinetics of the reactions of maleic anhydride, N-methylmaleimide, fumaronitrile, diethyl fumarate, and diethyl maleate with pyridinium and sulfonium ylides were studied in DMSO at 20 C. All of the reactions were found to follow a second-order rate law

Regioselective synthesis of 3-acylindolizines and benzo- analogues via 1,3-dipolar cycloadditions of N-ylides with maleic anhydride

3-Acylindolizines (5a-5f) and their benzo- analogues 1-acylpyrrolo[1,2-a] quinolines (6a-6f) and 1-acylpyrrolo[2,1-a]isoquinolines (7a-7i) are regioselectively synthesized by a convenient one pot reaction of the corresponding pyridinium (quinolinium, isoquinolinium) ylide with maleic anhydride (MA) in the presence of the mild oxidant tetrakispyridinecobalt(ii) dichromate (TPCD). These reactions proceed via a tandem reaction sequence of 1,3-dipolar cycloaddition of azomethine ylide with MA, anhydride hydrolysis and oxidative bisdecarboxylation of the primary cycloadducts followed by dehydrogenative aromatization of the dihydroindolizines. TPCD serves as both decarboxylation and dehydrogenation reagent in the reactions. These results show that TPCD is a promising new reagent for bisdecarboxylation of aliphatic carboxylates.

Controlling chemoselectivity-application of DMF di-t-butyl acetal in the regioselective synthesis of 3-monosubstituted indolizines

Among a number of DMF dialkyl acetals investigated for the regioselective synthesis of 3-acylindolizines, the di-t-butyl acetal, via its iminium intermediate readily formed in situ, provides the highest chemoselectivity for the intermolecular cyclization of picolinium salts. DMF di-t-butyl acetal was applied to the syntheses of a variety of 3-acylated indolizines including alkyl, aryl, and heteroaryl substituents.

SYNTHESIS OF INDOLIZINES

Disclosed are methods of preparing substituted indolizines represented by the following formula: comprising reacting a substrate represented by the following formula: with either the cyclization reagent of the following formula: or, a reagent prepared by reacting the compound represented the formula below with an alkylating agent: The variables in the above formulas are defined herein.

HETEROCYCLIC SYNTHESIS BY ELECTROCYCLIZATION OF EXTENDED DIPOLES: A NOVEL ACCESS TO THE INDOLIZINE AND QUINOLIZINE SYSTEMS

On thermal activation α-butenynyl substituted pyridine-N-oxides 4 undergo a multistep rearrangement affording 4-oxo-4H-quinolizines (8) and 2-acylindolizines (9).In the geometrical isomeriziation of E-4 to Z-4 annulated isoxazolidines (7) are involved as unstable intermediates.