17281-79-7

Upstream product

• 110-86-1 pyridine 
• 292638-85-8 acrylic acid methyl ester 
• 98-86-2 acetophenone 
• 2579-22-8 Phenylpropargyl aldehyde 
• 1658-42-0 methyl 2-pyridylacetate 
• 70-11-1 α-bromoacetophenone 
• 4636-16-2 iodoacetophenone 
• 100-47-0 benzonitrile 
• 316375-85-6 methyl indolizine-1-carboxylate 
• 1395895-89-2 methyl 5-phenyl-2-(pyridin-2-yl)pent-4-ynoate 
• 621-82-9 Cinnamic acid 
• 16883-69-5 N-phenacylpyridinium bromide 
• 922-67-8 propynoic acid methyl ester 

Downstream Products

• 133619-71-3 methyl 3-(α-hydroxybenzyl)indolizine-1-carboxylate 
• 133619-77-9 dimethyl 3,3'-(phenylmethylene)diindolizine-1-carboxylate 
• 189569-52-6 methyl 3-(1-phenylvinyl)indolizine-1-carboxylate 

Relevant academic research and scientific papers

Iodine-mediated one-pot synthesis of C-3 acylated indolizines from pyridines, aryl methyl ketones and acrylate derivatives

An I2/CuI-promoted multi-component reaction from pyridines, aryl methyl ketones and electron deficient acrylates has been accomplished in a “one-pot” manner, which provides a straightforward and efficient access to C-3 acylated indolizines. The

Preparation method of C-3 arylformylindolizine compounds

The invention discloses a preparation method of C-3 arylformylindolizine compounds. The method comprises the following steps: adding a metal additive, elemental iodine, a pyridine derivative, aromaticethanone, an electron deficient olefin and a base into

Catalyst-Free Annulation of 2-Pyridylacetates and Ynals with Molecular Oxygen: An Access to 3-Acylated Indolizines

A catalyst and additive-free annulation of 2-pyridylacetates and ynals under molecular oxygen was the first developed, affording 3-acylated indolizines in good to excellent yields. Molecular oxygen was used as the source of the carbonyl oxygen atom in indolizines. This approach was compatible with a wide range of functional groups, and especially it has been successfully extended to unsaturated double bonds and triple bonds, which were difficult to prepare by previous methods in a single step.

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.

One-pot synthesis of indolizine via 1,3-dipolar cycloaddition using a sub-equivalent amount of K2Cr2O7 as an efficient oxidant under base free conditions

A one-pot method for synthesizing multi-substituted indolizines from α-halo-carbonyl compounds, pyridines and electron deficient alkenes was developed. A sub-equivalent amount of potassium dichromate was used as an oxidant under base free conditions. The transformation developed should be of economic efficiency.

Facile access to 3-acylindoles through palladium-catalyzed addition of indoles to nitriles: The one-pot synthesis of indenoindolones

A palladium-catalyzed addition of indoles to nitriles, leading to 3-acylindoles, was reported, and the scope of nitriles was investigated. The strategy described provides a more efficient and atom-economical alternative to indenoindolones. It was found that alkenyl, carbonyl, halogen, methoxy, and nitro groups on aryl nitriles, which could offer opportunities for further synthetic transformations, are all compatible with the conditions. N-unprotected indoles with electron-rich groups show excellent reactivity towards this addition reaction. Under the optimized conditions, an array of indenoindolones are obtained in synthetic useful yields from readily available indoles and nitriles in one pot. The results also show that both the electron-poor and electron-rich substituents could be introduced to indoles and nitriles and that the halogen atoms were compatible under the current conditions.

A direct method for the synthesis of indolizine derivatives from easily available aromatic ketones, pyridines, and acrylonitrile derivatives

A concise and efficient strategy has been proposed to synthesize indolizine derivatives from easily available aryl or heteroaryl methyl ketones, pyridines, and acrylonitriles. The mechanistic pathway involved the integration of iodination, pyridinium ylid

Facile approach to diverse 3-acylated indolizines via a sequential Sonogashira coupling/iodocyclization process

Successful implementation of a sequential Pd-catalyzed Sonogashira cross-coupling/iodine-promoted 5-exo-dig cyclization procedure with pyridines bearing a terminal alkyne moiety provided direct and straightforward access to a diverse array of 3-acylated i

Palladium-catalyzed oxidative C-H bond and C=C double bond cleavage: C-3 acylation of indolizines with α,β-unsaturated carboxylic acids

A novel palladium-catalyzed C-3 acylation of indolizines with α,β-unsaturated carboxylic acids via C-H bond and C=C double bond cleavage under oxidative conditions is described. The regioselectivity is assisted by the carboxylic group, and the selection of the oxidant is crucial to the reaction.

Indolizines 4. The synthesis of new 3-vinylindolizines.

New 3-vinylindolizines have been synthesized by two methods.The first strategy calls for the Wittig olefination of 3-acylindolizines with methylenetriphenylphosphorane or methoxymethylenetriphenylphosphorane.The best yields are obtained when the ylid is formed at room temperature and the condensation in refluxing THF.The required 3-acylindolizines were obtained by direct acylation of indolizines or by 1,3-dipolar cyclo-additions to acylmethylpyridinium ylids.The following 3-isopropenylindolizines were made with good yields: unsubstituted (18, 85percent), 2-methyl (10, 98percent), 2-C6H5 (17, 95percent), 1-COOMe (20, 98percent), 1-COOMe-2-C6H5 (22, 91 percent), 1,2-di-COOMe (24, 58percent).Also synthesized are the following 3-α-styrylindolizines: 2-C6H5 (19, 99percent), 1-COOMe (21, 93percent), 1-COOMe-2-C6H5 (23, 87percent), 1,2-diCOOMe (25, 66percent). 3-(α-Methyl-β-methoxyvinyl)indolizines E (26, 40percent) and Z (27, 40percent) were also obtained.The second strategy involves the 1,3-dipolar cyclo-addition of dipolarophiles to allylpyridinium ylids.The following new 3-vinylindolizines have been synthesized: 1-carbomethoxy-3-vinylindolizine (30, 21percent), 1,2-dicarbomethoxy-3-vinylindolizine (31, 16percent), 1-carbomethoxy-3-β-styrylindolizine (33, 43percent), 3-β-styrylindolizine (34, 17percent), 1-carbomethoxy-3-(β-carbomethoxy)vinylindolizine 38 (31percent).