16883-69-5Relevant articles and documents
Synthesis of 2-aminoindolizines by 1,3-dipolar cycloaddition of pyridinium ylides with electron-deficient ynamides
Brioche, Julien,Meyer, Christophe,Cossy, Janine
, p. 2800 - 2803 (2015)
Electron-deficient ynamides, possessing an ynoate or an ynone moiety, have been successfully involved for the first time in a 1,3-dipolar cycloaddition with stabilized pyridinium ylides. These reactions afford an efficient and general access toward a variety of substituted 2-aminoindolizines which can serve as useful precursors for the synthesis of other more complex nitrogen heterocycles.
Ultrasound-promoted regioselective synthesis of chalcogeno-indolizines by a stepwise 1,3-dipolar cycloaddition
Vieira, Marcelo M.,Dalberto, Bianca T.,Coelho, Felipe L.,Schneider, Paulo H.
, (2020)
A series of new organochalcogen derivatives of indolizines was synthesized in moderate to excellent yields from pyridinium salts and chalcogeno-alkynes. The reaction can be carried out under thermal conditions or by sonochemical processes in short reaction times. The stepwise cycloaddition reaction forming chalcogeno-indolizines is regioselective and extends to a broad range of functional groups. Furthermore, novel chalcogeno-alkynes are reported and the first derivatives of teluro-indolizine are described. The influence of selenium functionalization on the photophysical properties of indolizines is also described, in which the compounds showed absorption in the UV–Vis region around 360 nm and emission in the blue-to-green region. Relatively low fluorescence quantum yield (?fl) values were calculated, in agreement with the chalcogen effect on other heterocycles.
Synthesis of tetrasubstituted pyridazines via cascade reactions of diazocarbonyl compounds with pyridinium ylides
Tomilov,Platonov,Dorokhov,Zhalnina
, p. 1252 - 1256 (2008)
Reactions of pyridinium ylides with diazocarbonyl compounds involve the formation of functionalized azine intermediates that can undergo intramolecular cyclocondensation into tetrasubstituted pyridazines provided the starting reagents contain carbonyl groups. Reactions of pyridinium ylides with diazo compounds were studied for various substituents in both the substrates.
Preparation of 1-trifluoroacetyl indolizines and their derivatives via the cycloaddition of pyridinium N-ylides with 4-4-ethoxy1-1,1,1-trifluorobut-3-en-one
Zhu, Shi-Zheng,Qin, Chao-Yue,Wang, Yan-Li,Chu, Qian-Li
, p. 183 - 187 (1999)
Under basic reaction conditions pyridinium or isoquinolinium N-ylides (C5H5N+ CH2YBr- or C9H7N+CH2YBr-, Y : CO2R, CN, PhCO) reacted readily with 4-ethoxyl-1,1,1-trifluorobut-3-en-2-one to give the corresponding 1-trifluoroacetyl substituted indolizines or pyrrolo-[1,2-a]isoquinolines. The molecular structure of 1-trifluoromethyl-3-methoxyl-pyrrolo-[1,2-a]isoquinoline is presented.
Stereoselective Cycloaddition of Pyridinium or Isoquinolinium Methylides with Olefinic Dipolarophiles and Subsequent Cycloadditions of the Cycloadducts with Nitrile Oxides
Tsuge, Otohiko,Kanemasa, Shuji,Takenaka, Shigeori
, p. 3631 - 3636 (1986)
Pyridinium or isoquinolinium methylides undergo highly stereo- and regioselective cycloadditions with olefinic dipolarophiles to form unstable tetrahydroindolizine derivatives.One of the two double bonds existing in the dihydro heteroaromatic ring of the cycloadducts reacts with nitrile oxides, in the same flask, in stereo-, regio-, and periselective fashions to lead to stable isoxazole-fused tetrahydroindolizines in good yields.
An efficient microwave accelerated three component reaction of phenacyl azides and pyridinium phenacyl salts: A facile greener approach to 2-amino-2-ene-1,4-diones/pyrrolidin-2-ones
Chimaladenne, Venkateswarlu,Manda, Ramesh,Gudipally, Ashok Reddy,Valluru, Krishna Reddy,Brahman, Pradeep Kumar,Somarapu, Vijaya Laxmi
, p. 2941 - 2949 (2020)
A mild and efficient base promoted, microwave assisted, green synthesis of 2-amino-2-ene-1,4-diones has been described by the decomposition of phenacyl azides followed by treatment with pyridinium salts of phenacyl bromides in aqueous media. A diverse range of substrates bearing electron-releasing and electron-withdrawing substituents were well tolerated and delivered corresponding 2-amino-2-ene-1,4-diones in good yields. Synthesized 2-amino-2-ene-1,4-diones have been further explored in the synthesis of various substituted 4-hydroxypyrrolidin-2-ones.
Benzoquinoline-based fluoranthene derivatives as electron transport materials for solution-processed red phosphorescent organic light-emitting diodes
Park, So-Ra,Shin, Dong Heon,Park, Sang-Mi,Suh, Min Chul
, p. 28520 - 28526 (2017)
A new electron transport material (ETM) with two fluoranthene and a benzoquinoline moiety was synthesized for the fabrication of solution-processed phosphorescent organic light-emitting diodes (PHOLEDs). In particular, we designed a bulky structure with a large twisted angle and improved thermal stability as compared to those of the common ETMs [e.g., 2,2′,2′′-(1,3,5-phenylene)tris(1-phenyl-1H-benzimidazole) (TPBI)] for device stability. As a result, we found that 4-(3-(fluoranthen-3-yl)-5-(fluoranthen-4-yl)phenyl)-2-phenyl-benzo[h]quinoline (FRT-PBQ) showed high glass transition temperature (Tg: ～184 °C) and moderately high electron transport behavior despite its bulky structural moieties. Moreover, we fabricated solution-processed red PHOLEDs with FRT-PBQ, and a relatively high current efficiency and external quantum efficiency of up to 20.7 cd A-1 and 15.5%, respectively, were achieved. In addition, the device lifetime was extended by a factor of 1.7 as compared to that of the device fabricated with TPBI as a common ETM.
Regioisomeric synthesis of dihydrofuro[2,3-d]pyrimidines in a diastereoselective manner involving nitrogen ylides in one-pot three-component reaction
Dutta, Leema,Sharma, Meenakshi,Bhuyan, Pulak J.
, p. 6654 - 6660 (2016)
Synthesized some novel regioisomers of furo[2,3-d]pyrimidines in a diastereoselective manner via one-pot three-component reaction of barbituric acids, aryl aldehydes and pyridinium bromides in the presence of triethylamine as base. Both the isomers were obtained in comparable ratio with excellent overall yield.
Synthesis and characterisation of extended π-bonding systems in cycloimmonium ylides derived from the 4,4′-bipyridine
Depature, Ludovic,Surpateanu, Gheorghe
, p. 2239 - 2254 (2002)
Disubstituted cycloimmonium ylides derived from the 4,4'-bipyridine with one, two or four ylidic systems in their molecular structure are described as stable compounds. Synthesis of some bridged 1,1'-disubstituted 4,4'-bipyridinium dimethylides in which 1,4- or 1,3-phenylene spacers may be used, provide some new macromolecular cycloimmonium ylides with spatially extended π-bonding system. These compounds were obtained by the chemical conversion of 4,4'-bipyridinium salts as viologens or bis-viologens, with acylating or carbamoylating agents, in basic media. The characterisation of all compounds has been mainly performed by 1H and 13C NMR spectroscopy.
Three-component synthesis of novel spirooxindole–furan derivatives using pyridinium salts
Baharfar, Robabeh,Asghari, Sakineh,Zaheri, Farya,Shariati, Narges
, p. 359 - 364 (2017)
A simple and efficient synthesis of novel spirooxindole–furan derivatives has been investigated by a modified version of the“interrupted” Feist–Bénary (IFB) reaction of isatin derivatives, 1,3-dicarbonyl compounds and N-phenacyl pyridinium salts in the presence of triethylamine. The reaction has been carried out under mild conditions in ethanol, and the products were obtained in good to moderate yields with a simple work-up procedure.
