- One-pot regio- and chemo-selective synthesis of thiaazatricyclododecane
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A highly regio- and chemo-selective heteroannulation protocol for the synthesis of unreported polysubstituted thiaazatricyclododecanes has been developed by a sequential four-component reaction of isoquinoline, 2-bromoacetophenones, aryl isothiocyanates,
- Alizadeh, Abdolali,Bagherinejad, Akram,Bayat, Fahimeh,Zhu, Long-Guan
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- Synthesis of novel fused heterocycle-oxa-aza-phenanthrene and anthracene derivatives via sequential one-pot synthesis in aqueous micellar system
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Oxa-aza-phenanthrene and anthracene derivatives which contain a bridgehead nitrogen are synthesized in an aqueous micellar system. The synthetic route is easy and yield is excellent. In this proposed method, solvent, base and surfactant are optimized and
- Srivastava, Madhulika,Singh, Jaya,Singh, Shyam B.,Tiwari, Kamleshwar,Pathak, Vijay K.,Singh, Jagdamba
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- New quinoline- and isoquinoline-based multicomponent methods for the synthesis of 1,1(3,3)-dicyanotetrahydrobenzoindolizines
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Convenient multicomponent methods for the synthesis of benzannulated dihydroindolizines based on quinoline or isoquinoline, malononitrile, aromatic aldehydes and α-halomethylcarbonyl compounds were developed. Several alternative protocols of using the reactants were studied, starting with separate generation of two most probable intermediates and ending with the four-component condensation of all reactants. The scope of applicability of these methods was found, depending on the initial compounds used. The reaction is highly stereoselective with predominant formation of one of the possible isomers.
- Sanin,Zubarev,Rudenko, A. Yu.,Rodinovskaya,Batuev,Shestopalov
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- Unprecedented access to functionalized pyrrolo[2,1-a]isoquinolines from the domino reaction of isoquinolinium ylides and electrophilic benzannulated heterocycles
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We have come across an unexpected reaction between electrophilic indoles and isoquinolinium methylides for accessing functionalized pyrrolo[2,1-a]isoquinolines. The reaction was found in general to yield the products in good yields. We also observed the f
- Babu, Sheba Ann,A. R., Rajalekshmi,P. R., Nitha,Omanakuttan, Vishnu K.,P., Rahul,Varughese, Sunil,John, Jubi
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supporting information
p. 1807 - 1817
(2021/03/14)
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- Silver-Promoted (4 + 1) Annulation of Isocyanoacetates with Alkylpyridinium Salts: Divergent Regioselective Synthesis of 1,2-Disubstituted Indolizines
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An unprecedented silver-promoted regioselective (4 + 1) annulation of isocyanoacetates with pyridinium salts is reported. The established protocol provides controlled, facile, and modular access to a range of synthetically useful N-fused heterocyclic scaffolds containing indolizines, pyrrolo[1,2-a]quinolines, pyrrolo[2,1-a]isoquinolines, and 1H-imidazo[4,5-a]indolizin-2(3H)-ones. A mechanistic pathway involving nucleophilic addition/protonation/elimination/cycloisomerization is proposed.
- Chen, Yan,Shatskiy, Andrey,Liu, Jian-Quan,K?rk?s, Markus D.,Wang, Xiang-Shan
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supporting information
p. 7555 - 7560
(2021/10/02)
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- Regio- And Stereoselectivity in the 1,3-Dipolar Cycloaddition Reactions of Isoquinolinium Ylides with Cyclopenta[ a ]acenaphthylen-8-ones
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A convenient regio- and diastereoselective synthesis of functionalized 5a,5b-dihydro-5 H,13 H -naphtho[1′′,8′′:4′,5′,6′]pentaleno[1′:3,4]pyrrolo[2,1- a ]isoquinolin-5-ones via 1,3-dipolar cycloaddition reaction of 8 H -cyclopenta[a]acenaphthylen-8-ones wi
- Yavari, Issa,Ravaghi, Parisa,Safaei, Maryam,Kayanian, Jasmine
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p. 1691 - 1695
(2020/09/02)
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- DMAP-Catalyzed Annulation Approach for Modular Assembly of Furan-Fused Chromenes
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With a tandem DMAP-catalyzed reaction between o-AQM, in which it is generated in situ from propargylic amine, and acyl carbene surrogate (from pyridinium ylide), a variety of polyarylated chromenes are assembled in good yields. This process does not require transition-metal catalyst and exhibits easy manipulation of the arene group and good functional group compatibility, particularly the -Br group which can be further transformed to other functionalities by cross-coupling reactions. The modular feature of o-AQM substrates and the simple operation procedures add further advantages to this synthetic method.
- He, Xinwei,Li, Ruxue,Choy, Pui Ying,Liu, Tianyi,Wang, Junya,Yuen, On Ying,Leung, Man Pan,Shang, Yongjia,Kwong, Fuk Yee
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supporting information
p. 9444 - 9449
(2020/12/21)
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- One-pot synthesis of pyrrolo[2,1-a]isoquinolines via tandem reactions of vinylselenonium salt, 2-bromoethanones, and isoquinoline
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An convenient and one-pot synthesis of pyrrolo[2,1-a]isoquinolines via the tandem reaction of methyl(phenyl)vinylselenonium salt with isoquinoline and 2-bromoethanones has been developed, which features very mild conditions, available substrates, simple experimental procedures, moderate to good yields, and wide functional group tolerance.
- Li, Yunxia,Liao, Minghong,Liu, Shanshan,Mao, Deshou,Sun, Qi,Tang, E.,Zhao, Yan
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p. 1563 - 1574
(2020/01/28)
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- DABCO-catalyzed multi-component domino reactions for the one-pot efficient synthesis of diverse and densely functionalized benzofurans in water
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An efficient, three-component strategy for the improved synthesis of a pharmaceutically interesting diverse kind of multi-functionalized benzofurans via one-pot two-step domino protocol with high diastereoselectivity in excellent yields has been established. The synthesis was achieved by reacting phenacyl bromides, N-heterocycles, aromatic aldehydes, and cyclic 1,3-dicarbonyl compounds in the presence of a catalytic amount of DABCO (1,4-diazabicyclo[2.2.2]octane) as an inexpensive, impressive, and readily available catalyst in water under reflux. In this process in total three new bonds (two C–C and one C–O) form in one pot. Short reaction time, excellent yields, no chromatographic purification, and evasion of environmentally hazardous or toxic catalysts and organic solvents in the entire reaction process may make this protocol very useful for academia and industry.
- Golchin, Sajedeh,Mosslemin, Mohammad Hossein,Yazdani-Elah-Abadi, Afshin,Shams, Nasim
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p. 1735 - 1749
(2017/02/15)
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- Transition-Metal-Free Synthesis of Indolizines from Electron-Deficient Alkenes via One-Pot Reaction Using TEMPO as an Oxidant
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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.
- Shi, Fei,Zhang, Yu,Lu, Zhaole,Zhu, Xiaolei,Kan, Weiqiu,Wang, Xiang,Hu, Huayou
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p. 413 - 420
(2016/01/28)
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- 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
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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.
- Wang, Chao,Hu, Huayou,Xu, Juanfang,Kan, Weiqiu
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p. 41255 - 41258
(2015/05/20)
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- One-pot two-step synthesis of 1-(ethoxycarbonyl)indolizines via pyridinium ylides
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Pyridinium salts Py+-CH2-EWG (EWG = CO2Et, CONEt2, CN, COMe, COPh) reacted with Michael acceptors Ar-CH=C(CO2Et)(Acc) (Acc = CO2Et, COMe, SO2Me, CONH2) at ambient temperature in the presence of base to give [3 + 2]-cycloadducts by stepwise [3 + 2]-cycloaddition of the intermediate pyridinium ylides. Treatment of the crude reaction mixtures with 1 equiv. of chloranil and atmospheric oxygen in the presence of sodium hydroxide gave 1-(ethoxycarbonyl)indolizines by dehydrogenation and elimination of the acceptor group (Acc). A good yield of indolizine was also obtained from Py +-CH2CN and iPr-CH=C(CO2Et)2, which indicates that this method is not restricted to aromatic Michael acceptors. Structurally related isoquinolinium salts react with Michael acceptors analogously to give pyrrolo[2,1-a]isoquinolines.
- Allgaeuer, Dominik S.,Mayr, Herbert
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supporting information
p. 6379 - 6388
(2013/10/21)
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- Amberlite-IRA-402 (OH) ion exchange resin mediated synthesis of indolizines, pyrrolo [1,2-a] quinolines and isoquinolines: Antibacterial and antifungal evaluation of the products
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A number of indolizines and pyrrolo[1,2-a]quinolines/isoquinolines were prepared from phenacyl pyridinium, quinolinium and isoquinolinium salts derived fromthe reaction of the heterocycles with 2-bromo acetophenone with alkynes and alkenes using amberlite-IRA-402 (OH) ion exchange resin as the base. Antibacterial and antifungal studies were carried out against thirteen bacterial and four fungal strains, which revealed that three derivatives (4a, 4b, 7a) out of fifteen are effective against all the thirteen strains and one derivative, 10, showed dual antibactericidal and antifungal efficacy.
- Hazra, Abhijit,Mondal, Shyamal,Maity, Arindam,Naskar, Subhendu,Saha, Pritam,Paira, Rupankar,Sahu, Krishnendu B.,Paira, Priyankar,Ghosh, Soma,Sinha, Chandrima,Samanta, Amalesh,Banerjee, Sukdeb,Mondal, Nirup B.
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body text
p. 2132 - 2140
(2011/06/21)
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- Synthesis of zwitterionic salts of pyridinium-meldrum acid and barbiturate through unique four-component reactions
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An efficient synthetic procedure for the preparation of the unusual charge-separated pyridinium-Meldrum acid and N,N-dimethylbarbiturate acid zwitterionic salts was developed though a unique one-pot fourcomponent reaction involving pyridine, aromatic aldehyde, Meldrum acid or N,N-dimethylbarbituric acid, and p-nitrobenzyl bromide in acetonitrile. By varying combinations of four components involving nitrogencontaining heterocycles, we conveniently established reactiveα-halomethylene compounds, aldehydes and β-dicarbonyl compounds a library of zwitterionic salts.
- Wang, Qi-Fang,Hui, Li,Hou, Hong,Yan, Chao-Guo
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supporting information; experimental part
p. 260 - 265
(2010/08/05)
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- 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
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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.
- Zhu, Shi-Zheng,Qin, Chao-Yue,Wang, Yan-Li,Chu, Qian-Li
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p. 183 - 187
(2007/10/03)
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- SYNTHESIS AND STRUCTURAL STUDY ON Α-SUBSTITUED-1-STYRYLPYRIDINIUM SALTS. REINVESTIGATION OF KROHNKE CONDENSATION
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Kroehnke condensation of several cycloimmonium salts with p-dimethylaminobenzaldehyde has been studied.X-Ray diffraction, IR and Raman spectra, 1H- and 13C-NMR and UV spectra of the products are discussed, being compared, when necessary, with the starting pyridinium salts.All compounds showed the Z configuration, corresponding to the more stable structure, except one, in which steric factors were predominant.
- Alvarez-Builla, J.,Novella, J. L.,Galvez, E.,Smith, P.,Florencio, F.,et al.
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p. 699 - 708
(2007/10/02)
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- Preparation of Tetrahydroindolizines from Pyridinuim and Isoquinolinium Ylides
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Carbonyl- and nitrile-stabilised pyridinium and cyclic azonium methylides condense with chalcones to form tetrahydroindolizines and analogous fused pyrrolidines.The stereochemistry is illuminated by 13C and 1H n.m.r. spectroscopy.Several incorrect literature structures are rectified.
- Katritzky, Alan R.,Grzeskowiak, Nicholas E.,Alvarez-Builla, Julio
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p. 1180 - 1185
(2007/10/02)
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- Studies on Cycloimmonium Ylids: Synthesis of Some 2,4,6-Triarylpyridines via Isoquinolinium Ylids
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Aroylmethylene-isoquinolinium ylids on reaction with substituted benzylidenacetophenones in gl. acetic acid containing ammonium acetate afford 2,4,6-triarylpyridines (4a-j).The reaction seems to proceed via the intermediacy of pentane-1,5-dionylisoquinoli
- Tewari, R. S.,Dubey, A. K.
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p. 153 - 154
(2007/10/02)
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- Imidazo (1,2-B) isoquinoline derivatives
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5,10-Dihydro-imidazo(1,2b)isoquinolines substituted in the 2- and/or 3-position(s) by an aromatic group have analgesic, anti-inflammatory or anti-pyretic activity. Except for 2-phenyl-5,10-dihydroimidazo(1,2b)isoquinoline, they are believed to be novel co
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