- Revisiting the three component synthesis of isoxazolo[5,4-b]pyridines, 4-aryl-3,7,7-trimethyl-isoxazolo[5,4-b]quinolin-5(6H)-ones and related heterocycles
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The one-step three-component microwave assisted synthesis between aromatic aldehydes with tetronic acid or indan-1,3-dione readily formed the Knoevenagel adducts that underwent addition of 3-methylisoxazol-5-amine 1 to form the isoxazolo[5,4-b]pyridine pr
- Lingham, Anthony R.,Hawley, John A.,Greaves, Tamar,Jackson, Neale,Antolasic, Frank,Hügel, Helmut M.
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Read Online
- Microwave-promoted, catalyst-free, multi-component reaction of proline, aldehyde, 1,3-diketone: One pot synthesis of pyrrolizidines and pyrrolizinones
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One-pot, three-component preparation of the pyrrolizidine and pyrrolizinone derivatives in moderate to good yield is reported. The synthesis is facilitated by microwave irradiation of proline, aromatic aldehyde, and 1,3-diketone such as 2-arylmethylene-in
- Manjappa, Kiran B.,Peng, Yu-Ting,Jhang, Wei-Fang,Yang, Ding-Yah
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Read Online
- Mild Darzens Annulations for the Assembly of Trifluoromethylthiolated (SCF3) Aziridine and Cyclopropane Structures
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We report mild new annulation approaches to trisubstituted trifluoromethylthiolated (SCF3) aziridines and cyclopropanes via Darzens inspired protocols. The products of these anionic annulations, rarely studied previously, possess attractive features rendering them valuable building blocks for synthesis platforms. In this study, trisubstituted acetophenone nucleophiles bearing SCF3 and bromine substituents in their α position were shown to undergo [2 + 1] annulations with vinyl ketones and tosyl-protected imines under mild reaction conditions.
- Delost, Michael D.,Njardarson, Jon T.
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supporting information
p. 6121 - 6125
(2021/08/16)
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- Synthesis of novel spiro-tetrahydroquinoline derivatives and evaluation of their pharmacological effects on wound healing
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A highly diastereoselective method for the synthesis of novel spiro-tetrahydroquinoline derivatives is reported here, using a one-pot reaction method. All compounds were characterized by1 H-nuclear magnetic resonance (NMR) and mass spectroscopy
- Liou, Yan-Cheng,Lin, Yan-An,Wang, Ke,Yang, Juan-Cheng,Jang, Yeong-Jiunn,Lin, Wenwei,Wu, Yang-Chang
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- Leishmanicidal and cytotoxic activities and 4D-QSAR of 2-arylidene indan-1,3-diones
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The indan-1,3-dione and its derivatives are important building blocks in organic synthesis and present important biological activities. Herein, the leishmanicidal and cytotoxicity evaluation of 16 2-arylidene indan-1,3-diones is described. The compounds w
- de Souza, Ana P. M.,Costa, Maria C. A.,de Aguiar, Alex R.,Bressan, Gustavo C.,de Almeida Lima, Graziela D.,Lima, Wallace P.,Borsodi, Maria P. G.,Bergmann, Bartira R.,Ferreira, Márcia M. C.,Teixeira, Róbson R.
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- Highly diastereoselective spiro-cyclopropanation of 2-arylidene-1,3-indanediones and dimethylsulfonium ylides
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A highly diastereoselective spiro-cyclopropanation reaction of 2-arylidene-1,3-indanediones and dimethylsulfonium ylides has been developedviabase-induced annulation. This efficient and simple protocol features simple operations, mild conditions and excellent functional group compatibility. A variety of structurally interesting spiro-cyclopropanes were prepared in excellent yields and diastereomeric ratios (up to 97% yield and 20?:?1 dr). Also, ring expansion of the cyclopropanation product to quickly deliver a complex indeno[1,2-c]pyridazine structure showcased an interesting application of this method.
- Huang, Jie,Lee, Kevin,Ma, Ping,Sun, Shaofa,Wang, Gangqiang,Wang, Jian,Wu, Yang,Xing, Yalan
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supporting information
p. 18776 - 18780
(2021/10/26)
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- Phosphine-Catalyzed Cascade Michael Addition/[4+2] Cycloaddition Reaction of Allenoates and 2-Arylidene-1,3-indanediones
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The phosphine-catalyzed cascade Michael addition/[4+2] cycloaddition reaction of tetrahydrobenzofuranone-derived allenoates and 2-arylidene-1,3-indanediones has been reported, affording spirocyclic 1,3-indanedione derivatives in moderate to high yields wi
- Shi, Wangyu,Mao, Biming,Xu, Jiaqing,Wang, Qijun,Wang, Wei,Wu, Yongjun,Li, Xuefeng,Guo, Hongchao
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supporting information
p. 2675 - 2680
(2020/03/26)
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- A vinylogous Michael addition-triggered quadruple cascade reaction for the enantioselective generation of multiple quaternary stereocenters
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An efficient organocatalytic quadruple cascade reaction resulting in spiroxindole scaffolds bearing five quaternary stereocenters is reported. The complex cascade reaction is triggered by the scarcely explored vinylogous Michael addition of 3-alkylidene o
- Yang, Shu-Mei,Karanam, Praneeth,Wang, Min,Jang, Yeong-Jiunn,Yeh, Yu-Sheng,Tseng, Ping-Yao,Ganapuram, Madhusudhan Reddy,Liou, Yan-Cheng,Lin, Wenwei
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supporting information
p. 1398 - 1401
(2019/02/05)
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- Zirconium catalyzed synthesis of 2-arylidene Indan-1,3-diones and evaluation of their inhibitory activity against NS2B-NS3 WNV protease
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A simple and efficient Knoevenagel procedure for the synthesis of 2-arylidene indan-1,3-diones is herein reported. These compounds were prepared via ZrOCl2·8H2O catalyzed reactions of indan-1,3-dione with several aromatic aldehydes and using water as the
- Oliveira, Ana Flávia C. da S.,de Souza, Ana Paula M.,de Oliveira, André S.,da Silva, Milene L.,de Oliveira, Fabrício M.,Santos, Edjon G.,da Silva, ítalo Esposti P.,Ferreira, Rafaela S.,Villela, Filipe S.,Martins, Felipe T.,Leal, Daniel H.S.,Vaz, Boniek G.,Teixeira, Róbson R.,de Paula, Sergio O.
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supporting information
p. 98 - 109
(2018/03/09)
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- Synthesis of highly functionalized indeno[1,2-b]furans
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Some novel functionalized indeno[1,2-b]furans were synthesized from the reaction of indandione/indanone and aldehydes at room temperature followed by the reaction of the Knoevenagel condendensed intermediate with 4-hydroxycoumarins in the presence of iodi
- Dutta, Leema,Bhuyan, Pulak J.
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p. 3545 - 3548
(2017/10/06)
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- Chemo- and Diastereoselective Construction of Indenopyrazolines via a Cascade aza-Michael/Aldol Annulation of Huisgen Zwitterions with 2-Arylideneindane-1,3-diones
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A cascade aza-Michael/Aldol annulation of 2-arylideneindane-1,3-diones with in situ generated Huisgen zwitterions has been developed. This reaction afforded the desired products in moderate to good yields (up to 87%) with excellent chemo- and diastereoselectivity (up to 20:1). This strategy allows facile diastereoselective preparation of biologically important indenopyrazoline derivatives containing two contiguous chiral centers including a quaternary stereogenic center. (Figure presented.).
- Li, Yuming,Zhang, Haikun,Wei, Rong,Miao, Zhiwei
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supporting information
p. 4158 - 4164
(2017/10/11)
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- Multicomponent synthesis of new generation of arylindolylmethyl-1,3-indandiones using bis ionic liquid [BDBDIm]Br
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Background: In recent years, an increasing interest has been focused on the synthesis of 2-substituted 1,3-indandione compounds owing to their significant biological activity. It is well known that indandione and related compounds exhibit a wide range of
- Nikpassand, Mohammad,Fekri, Leila Zare,Bahrami, Farahnaz
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p. 629 - 635
(2017/01/13)
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- Synthesis and thermal transformations of spiro-fused N- phthalimidoaziridines Dedicated to Professor Armin de Meijere on the occasion of his 75th birthday
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Oxidation of N-aminophthalimide in the presence of 2-arylideneinden-1,3- diones with electron-withdrawing substituents gives the corresponding 3-aryl-1-phthalimidospiro[aziridine-2,2′-indene]-1′,3′-diones in good yields. Heating these aziridines with stan
- Pankova, Alena S.,Kuznetsov, Mikhail A.
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supporting information
p. 2499 - 2503
(2014/05/06)
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- Direct β-acylation of 2-arylidene-1,3-indandiones with acyl chlorides catalyzed by organophosphanes
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We have developed an organophosphane-catalyzed direct β-acylation of a series of conjugated systems bearing ketone, amide and ester functionalities using acyl chlorides as trapping reagents. A wide variety of highly functional ketone derivatives were gene
- Lee, Chia-Jui,Sheu, Chia-Ning,Tsai, Cheng-Che,Wu, Zong-Ze,Lin, Wenwei
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supporting information
p. 5304 - 5306
(2014/05/06)
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- Aqueous extract of Balanites roxburghii fruit: A green dispersant for C-C bond formation
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An aqueous biosurfactant solution, a biobased green acidic catalyst for Knoevenagel condensation of 1,3-indanedione with aryl aldehydes and tandem Knoevenagel-Michael reaction of 3-methyl-1-phenylpyrazole with aryl aldehydes, has been reported for the fir
- Barge, Madhuri,Salunkhe, Rajashri
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p. 31177 - 31183
(2014/08/05)
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- Determination of thermodynamic affinities of various polar olefins as hydride, hydrogen atom, and electron acceptors in acetonitrile
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A series of 69 polar olefins with various typical structures (X) were synthesized and the thermodynamic affinities (defined in terms of the molar enthalpy changes or the standard redox potentials in this work) of the polar olefins obtaining hydride anions, hydrogen atoms, and electrons, the thermodynamic affinities of the radical anions of the polar olefins (X ?-) obtaining protons and hydrogen atoms, and the thermodynamic affinities of the hydrogen adducts of the polar olefins (XH?) obtaining electrons in acetonitrile were determined using titration calorimetry and electrochemical methods. The pure Ci - 'C π-bond heterolytic and homolytic dissociation energies of the polar olefins (X) in acetonitrile and the pure Ci - 'C π-bond homolytic dissociation energies of the radical anions of the polar olefins (X?-) in acetonitrile were estimated. The remote substituent effects on the six thermodynamic affinities of the polar olefins and their related reaction intermediates were examined using the Hammett linear free-energy relationships; the results show that the Hammett linear free-energy relationships all hold in the six chemical and electrochemical processes. The information disclosed in this work could not only supply a gap of the chemical thermodynamics of olefins as one class of very important organic unsaturated compounds but also strongly promote the fast development of the chemistry and applications of olefins.
- Cao, Ying,Zhang, Song-Chen,Zhang, Min,Shen, Guang-Bin,Zhu, Xiao-Qing
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p. 7154 - 7168
(2013/08/23)
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- Efficient example of cross-linked polymeric catalysed synthesis of 7H-benzo[h]indeno[1,2-b]quinolin-8-one and 8H-naphtho[2,3-h]indeno[1,2-b] quinolin-9-one
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Cross-linked poly(2-acrylamido-2-methyl propane sulphonic acid) (AMPS) was found to be an efficient heterogeneous catalyst for direct synthesis of 7H-benzo[h]indeno[1, 2-b]quinolin-8-one and 8Hnaphtho[ 2, 3-h]indeno[1, 2-b]quinolin-9-one derivatives throu
- Sandaroos, Reza,Vadi, Mehdi,Damavandi, Saman
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p. 1497 - 1501
(2014/04/03)
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- Phosphine-catalyzed [4 + 2] annulation of γ-substituent allenoates: Facile access to functionalized spirocyclic skeletons
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The first phosphine-catalyzed [4 + 2] annulation of γ-substituted allenoates with 2-arylidene-1H-indene-1,3(2H)-diones is disclosed. In the reaction, the γ-substituted allenoate serves as a new type of 1,4-dipolar synthon; this broadens the application of
- Li, Erqing,Huang, You,Liang, Ling,Xie, Peizhong
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supporting information
p. 3138 - 3141
(2013/07/26)
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- Clean synthesis of 2-arylideneindan-1,3-diones in water
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A high-yield synthesis of 2-arylideneindan-1,3-diones in water was achieved by the Knoevenagel condensation of indan-1,3-dione with aromatic aldehydes at ambient temperature avoiding the addition of any catalyst. The procedure is simple, efficient, as wel
- Yang, Peng Hui,Zhang, Qun Zheng,Sun, Wei
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experimental part
p. 1063 - 1068
(2012/08/28)
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- Enantioselective synthesis of spirocyclic cyclopentenes: Asymmetric [3+2] annulation of 2-arylideneindane-1,3-diones with MBH carbonates derivatives catalyzed by multifunctional thiourea-phosphines
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The [3+2] annulation reactions of 2-arylideneindane-1,3-diones with Morita-Baylis-Hillman (MBH) carbonates proceeded smoothly in the presence of multifunctional thiourea-phosphines to produce the corresponding quaternary carbon centered spirocyclic cyclop
- Hu, Fangle,Wei, Yin,Shi, Min
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supporting information; experimental part
p. 7911 - 7919
(2012/10/08)
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- Solvent-free one pot synthesis of indenoquinolinones catalyzed by iron(III) trifl ate
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A green three-component one pot condensation synthesis of 16 indenoquinolinone from aromatic aldehydes, 1-aminonaphthalene or 1-aminoanthracene and 1,3-indanedione catalyzed by Fe(OTf)3 is described. The isolated yields ranged from 80 % to 92 %
- Damavandi, Saman,Sandaroos, Reza
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experimental part
p. 121 - 124
(2011/11/12)
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- Asymmetric synthesis of multi-substituted spiro[5,5]undecane-1,5,9-triones via organocatalytic three-component reaction
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The asymmetric domino three-component Knoevanagel-Diels-Alder addition (ATCDA) reaction, as an important methodology, has been utilized to construct complex product from ordinary starting materials. In this report, many typical organoamine catalysts were investigated to achieve highly efficient asymmetric three-component reaction of enones 2, aldehydes 3 and Meldrum's acid 4. Various pharmacological multi-substituted spiro[5,5]undecane-1,5,9-triones promoted by 9-amino-9-deoxy-epi-quinine 1 g in one-pot, were obtained in moderate to good yields (up to 81%) with excellent diastereo-(>99:1 dr) and enantioselectivities (up to 97% ee). Meanwhile, based on the controlled experiments and analytical data, a reasonable mechanism of dual-activity for this reaction has been proposed.
- Shi, Jian,Liu, Yangbin,Wang, Min,Lin, Lili,Liu, Xiaohua,Feng, Xiaoming
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supporting information; experimental part
p. 1781 - 1787
(2011/04/15)
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- Sulfamic acid-catalyzed, three-component, one-pot synthesis of [1,2,4]Triazolo/benzimidazolo quinazolinone derivatives
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An efficient and convenient approach is reported for three-component, one-pot synthesis of the [1,2,4]triazolo/benzimidazolo quinazolinones by condensation of 2-amino benzimidazole or 3-amino-1,2,4-triazole as amine sources with dimedone and different ald
- Heravi, Majid M.,Derikvand, Fatemeh,Ranjbar, Leila
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scheme or table
p. 677 - 685
(2011/03/21)
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- Unexpected formation of fluorine-containing multiply substituted dispirocyclohexanes from the reaction of ethyl-4,4,4-trifluoro-1,3- dioxobutanoate and 2-arylideneindane-1,3-diones
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In the presence of a catalytic amount of piperidine (10 mol%), reaction of ethyl 4,4,4-trifluoro-3-oxobutanoate 3 and 2-arylidene-indane-1,3-diones 4 gave the unexpected fluorine-containing multiply substituted dispirocyclohexanes 5 in good yields. The st
- Dai, Baifan,Song, Liping,Wang, Pengyuan,Yi, Hai,Cao, Weiguo,Jin, Guifang,Zhu, Shizheng,Shao, Min
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scheme or table
p. 1842 - 1846
(2009/12/04)
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- Synthesis and antimicrobial study of novel 1-aryl-2-oxo-indano[3,2-d] pyrido/pyrimido[1,2-b]pyrimidines
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A series of 2-(arylidene)-indan-1, 3-diones 1 were prepared by Knoevenagel reaction between indane-1,3-dione and the appropriate araldehydes. The α,β-enones 1 have been used as a component of Michael addition with equimolar amounts of 2-aminopyridine/2-am
- Sarvesh, Pandey K.,Nizamuddin, Khan
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experimental part
p. 418 - 423
(2009/04/04)
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- Synthesis of 2-(aryl methylene)-(1H)-indane-1,3-(2H)-diones as potential fungicidal and bactericidal agents
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Reaction of diethyl phthalate 1 and ethyl acetate 2 in the presence of sodium metal and ethanol affords indane-1, 3-dione 3, which have been substituted at C-2 position with different aromatic aldehydes 4, to yield their respective aryl derivatives of indane-1,3-dione 5a-h. These derivatives are evaluated for their antifungal and antibacterial activity. The structures of all the compounds are determined by IR, 1H NMR and mass spectrometry.
- Meena,Shankar,Ramseshu,Giles,Prakash,Venkataraman
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p. 1572 - 1575
(2007/10/03)
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- Solvent-free synthesis of 2-arylideneindan-1,3-diones in the presence of magnesium oxide or silica gel under grinding
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The solvent-free synthesis of 2-arylideneindan-1,3-diones can be achieved in the presence of MgO or silica gel under grinding. This process is simple, efficient, and environmentally benign. Copyright Taylor & Francis, Inc.
- Wu, Danyi,Ren, Zhongjiao,Cao, Weiguo,Tong, Weiqi
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p. 3157 - 3162
(2007/10/03)
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- Direct organocatalytic asymmetric heterodomino reactions: The Knoevenagel/Diels-Alder/epimerization sequence for the highly diastereoselective synthesis of symmetrical and nonsymmetrical synthons of benzoannelated centropolyquinanes
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Amino acids and amines have been used to catalyze three component hetero-domino Knoevenagel/Diels-Alder/epimerization reactions of readily available various precursor enones (1a-1), aldehydes (2a-p), and 1,3-indandione (3). The reaction provided excellent
- Ramachary,Anebouselvy,Chowdari, Naidu S.,Barbas III, Carlos F.
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p. 5838 - 5849
(2007/10/03)
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- 1,3-Dipolar cycloadditions of arylcarbonitrile oxides and diaryl nitrilimines with some 2-arylmethylene-1,3-indanediones; regiochemistry of the reactions
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Ring-closure reaction affording spiroisoxazolines and spiropyrazolines via a 1,3-dipolar cycloaddition between the title compounds, occurs with high regioselectivity.
- Boudriga, Sarra,Askri, Mohiedinne,Gharbi, Rafik,Rammah, Mohamed,Ciamala, Kabula
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p. 204 - 207
(2007/10/03)
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- Reaction of 2-benzoyl-1,2-dihydroisoquinoline-1-carbonitrile tetrafluoroborate salt with 2-arylmethylene-1,3-indanediones. Regio- and stereochemistry of the reaction. Formation of spiro compounds
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The regio- and stereochemistry of spiro-adducts derived from [4+2] cycloaddition between the title compounds were deduced by 1H NMR data and the elucidated structure of the tetrasubstituted pyrroles obtained by acidic hydrolysis.
- Boudriga, Sarra,Askri, Mohiedinne,Rammah, Mohamed,Monnier-Jobe, Karin
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p. 208 - 210
(2007/10/03)
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- The First Organocatalytic Hetero-Domino Knoevenagel-Diels-Alder-Epimerization Reactions: Diastereoselective Synthesis of Highly Substituted Spiro[cyclohexane-1,2′-indan]-1′,3′ ,4-triones
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L-Proline and pyrrolidine catalyzed the three component hetero-domino Knoevenagel-Diels-Alder-Epimerization reactions of readily available precursors enones 1a-i, arylaldehydes 2a-i and 1,3-indandione 3 to furnish highly substituted prochiral spiro[cycloh
- Ramachary,Chowdari, Naidu S.,Barbas III, Carlos F.
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p. 1910 - 1914
(2007/10/03)
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- Use of Functionalised Ynamines in a Hetero-Diels-Alder Approach to Dihydronaphtholpyrans and Indenopyrans
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Reaction of the ynamine ester methyl 3-(pyrrolidin-1-yl)prop-2-ynoate 5 with 2-(4-nitrobenzylidene)-1-tetralone 1 results in a very poor yield of the chromatographically labile 4-aryl-5,6-dihydro-4H-naphtholpyran 8 along with the α-pyrone 10.Increa
- Bloxham, Jason,Dell, Colin P.
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p. 3055 - 3060
(2007/10/02)
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- New Aspects in the Reaction of Azomethines with Cyclic CH-Acidic Compounds
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Treatment of substituted benzylidene anilines 1a - f with cyclic CH-acidic compounds 2a - m in ethanol at room temperature yields in addition/elimination reactions the corresponding arylidene derivatives 4 and the 2:1 adducts 5.The addition products 3, which are formed as intermediates, could not be isolated in any case.The donor/acceptor effect of the substituents on the benzylidene moiety influences to a significant extent the reactivity towards the azomethine carbon. Keywords.Azomethine; CH-Acidic compound; Addition/elimination reaction.
- Hennig, Lothar,Alva-Astudillo, Mario,Mann, Gerhard,Kappe, Thomas
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p. 571 - 580
(2007/10/02)
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- A convient route to polyfunctionalised indeno[1,2-b]pyran derivatives
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2-Arylidene-1,3-indanediones undrgo facile formal hetero-Diels-Alder cycloadditions with ynamines bearing electron-withdrawing groups yielding polyfunctionalised indeno[1,2-b]pyrans.
- Bloxham,Dell
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p. 4051 - 4054
(2007/10/02)
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- 5-Arylidene 1,3-Dimethylbarbituric Acid Derivatives, Mild Organic Oxidants for Allylic and Benzylic Alcohols
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Various 5-arylidene 1,3-dimethylbarbituric acid derivatives and closely related compounds were synthesized as models of redox coenzymes and used for oxidation of alcohols.Under mild neutral conditions, 5-arylidene 1,3-dimethylbarbituric acid derivatives, especially those having an electron-withdrawing group on the aromatic ring, effectively oxidized allylic and benzylic alcohols to the corresponding carbonyl compounds.The relationship between the oxidizing ability and the structure of the oxidant (coenzyme model) was investigated and it was found that the electron density on the carbon-carbon double bond is a critical factor for the oxidation.In the case of the deuterium-labeled compound, the observed value of normal and primary isotope effect was 3.3 and so it was concluded that mechanism of this oxidation mainly involves the hydride transfer from the alcohol.An electrochemical investigation was also carried out and the redox potentials of the coenzyme models, 5-arylidene 1,3-dimethylbarbituric acid derivatives and related compounds, were measured.Keywords - 5-arylidene 1,3-dimethylbarbituric acid; coenzyme model; oxidation; allylic alcohol; benzylic alcohol; oxidation mechanism; hydride transfer; primary isotope effect; cyclic voltammetry; redox potential
- Tanaka, Kiyoshi,Chen, Xing,Kimura, Teiji,Yoneda, Fumio
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- SYNTHESIS OF 5-OXOINDENOPYRIDINIUM SALTS
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When N-methylated 4-aryl-5-oxo-4,5-dihydroindenopyridines are oxidized with hydrogen peroxide in the presence of perchloric acid, in addition to the formation of the indenopyridinium perchlorates, cleavage of the dihydropyridine ring occurs, giving
- Zandersons, A. Z.,Lusis, V. K.,Mutsenietse, D. Kh.,Dubur, G. Ya.
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- Reaction of selenonium monoketoylides with 2-arylideneindanediones
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The reaction of selenonium monoketoylide with 2-arylidene-1,3-indanediones was investigated.Dihydrofurans with various structures or 2-(α-phenacylarylidene)-1,3-indanediones are formed, depending on the nature of the arylidene group.
- Magdesieva, N. N.,Sergeeva, T. A.
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p. 1622 - 1624
(2007/10/02)
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