- Visible Light-Promoted Selenylation/Cyclization of Enaminones toward the Formation of 3-Selanyl-4H-Chromen-4-Ones
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A simple and efficient visible-light-promoted selenylation/cyclization of enaminones have been realized for the practical synthesis of 3-selanyl-4H-chromen-4-ones. This reaction is performed in the mild conditions, no transition metal catalyst or photocatalysts and no additional oxidants are required. In addition, the 3-selanyl-4H-chromen-4-ones could be easily converted to selanyl-functionalized pyrimidines by reacting with benzamidine substrates. (Figure presented.).
- Liu, Hao-Yang,Zhang, Jia-Rong,Huang, Guo-Bao,Zhou, Yi-Huan,Chen, Yan-Yan,Xu, Yan-Li
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supporting information
p. 1656 - 1661
(2021/02/12)
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- TBN-triggered, manipulable annulations of: O -hydroxyarylenaminones for divergent syntheses of oximinochromanones and oximinocoumaranones
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Divergent synthesis provides an indispensable route to rapid acquisition of structurally diverse chemical scaffolds from identical starting materials. Herein, we describe unprecedented divergent annulations of o-hydroxyarylenaminones promoted by tert-butyl nitrite (TBN) under mild conditions. Two different types of benzo-oxa-heterocycle, including oximinochromanones and oximinocoumaranones, were smoothly assembled with a broad substrate scope and good functional group compatibility.
- Chen, Kai,Qian, Yu-En,Xiang, Hao-Yue,Xiao, Jun-An,Yang, Hua,Zhao, Qing-Lan,Zheng, Lan
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supporting information
p. 12285 - 12288
(2021/12/07)
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- T3P mediated domino C(sp2)-H sulfenylation/annulation of enaminones and methylsulfinyls for the synthesis of chromone thioether derivatives
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A new regioselective method for the synthesis of 3-(methylthio)-4H-chromen-4-one and 3-(phenylthio)-4H-chromen-4-one derivatives has been developed. The reaction between o-hydroxy-phenyl-functionalized enaminones and methylsulfinyl derivatives using T3P gave good yields of chromone thioether derivatives. The reaction proceeds via domino chromone ring construction and C(sp2)-H bond sulfenylation under transition-metal-free conditions.
- Balakrishna,Gudipati, Ramakrishna,Kandula, Venu,Yennam, Satyanarayana,Uma Devi,Behera, Manoranjan
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supporting information
p. 2458 - 2463
(2019/02/14)
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- Zn(OTf)2-Catalyzed Formal [3 + 3] Cascade Annulation of Propargylic Alcohols with 2-Aminochromones: Accessing the Chromeno[2,3- b]pyridines
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A Zn(OTf)2-catalyzed formal [3 + 3] cascade annulation strategy for the synthesis of functionalized chromeno[2,3-b]pyridines has been developed using propargylic alcohols and 2-aminochromones as the substrates. The protocol provides a convenien
- Tong, Pei,Sun, Zhou,Wang, Shutao,Zhang, Yuan,Li, Ying
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p. 13967 - 13974
(2019/10/16)
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- Application of E1cB Elimination in Asymmetric Organocatalytic Cascade Reactions to Construct Polyheterocyclic Compounds
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By introducing a carbon functionality at 2-position of chromane, the formal asymmetric functionalization of the 3-position of 2-substituted chromane has been realized via a highly chemo-, regio-, and stereoselective organocatalytic cascade reaction in a sequential one-pot manner involving an E1cB mechanism governed ring-opening process. Critical to our success was the design of a chiral dipeptide-based bifunctional acid-base organocatalyst, which exhibited high catalytic activity at low catalyst loading (1-0.1 mol %), leading to biologically interesting polyheterocyclic compounds.
- You, Zhi-Hao,Chen, Ying-Han,Tang, Yu,Liu, Yan-Kai
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supporting information
p. 8358 - 8363
(2019/10/16)
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- Iron-Catalyzed Regioselective Decarboxylative Alkylation of Coumarins and Chromones with Alkyl Diacyl Peroxides
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A facile iron-catalyzed decarboxylative radical coupling of alkyl diacyl peroxides with coumarins or chromones has been developed, affording a highly efficient approach to synthesize a variety of α-alkylated coumarins and β-alkylated chromones. The reaction proceeded smoothly without adding any ligand or additive and provided the corresponding products containing a wide scope of functional groups in moderate to excellent yields. This protocol was highlighted by its high regioselectivity, readily available starting materials, and operational simplicity.
- Jin, Can,Sun, Bin,Xu, Tengwei,Yan, Zhiyang,Zhang, Xun
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supporting information
p. 1585 - 1591
(2019/08/07)
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- Selectfluor-Mediated Tandem Cyclization of Enaminones for the Synthesis of 3-Fluorochromones
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An efficient synthesis of various 3-fluorochromones (3-fluoro-4 H -chromene-4-ones) from enamino ketones by using Selectfluor is described. The key step in the synthesis involves tandem fluorination and cyclization to form 3-fluorochromones in good yields. The significant features of this method include simple operational procedures, a high purity of the product, and excellent regioselectivity.
- Behera, Manoranjan,Chatterjee, Anindita,Kandula, Venu,Mallesham, Poosa,Raghavulu, K.,Thota, Pradeep Kumar,Yennam, Satyanarayana
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p. 2295 - 2299
(2019/12/11)
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- An Efficient Microwave-Assisted Propylphosphonic Anhydride (T3P )-Mediated One-Pot Chromone Synthesis via Enaminones
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An efficient synthesis of 4 H -chromene-4-ones via enamino ketones, with cyclization by using T3P under microwave heating is described. This is the first report for the synthesis of chromones by using T3P . Significant features of this method include short reaction times and high-purity products.
- Balakrishna,Kandula, Venu,Gudipati, Ramakrishna,Yennam, Satyanarayana,Devi, P. Uma,Behera, Manoranjan
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supporting information
p. 1087 - 1091
(2018/04/30)
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- Convenient and Rapid Synthesis of 3-Selenocyanato-4 H -chromen-4-ones
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A sequential one-pot, simple and convenient method is described for the synthesis of 3-selenocyanato-4 H -chromen-4-ones by addition, first of DMF-DMA and then of triselenodicyanide as electrophile.
- Kosso, Anne Roly Obah,Broggi, Julie,Redon, Sébastien,Vanelle, Patrice
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supporting information
p. 1215 - 1218
(2018/03/26)
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- Expedient chemoselective and catalyst-free synthesis of 3,3-difluorochroman-4-ones from o-hydroxyarylenaminones and Selectfluor
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An expedient and mild strategy for the synthesis of unconventional 2-(dimethylamino)-3,3-difluorochroman-4-one derivatives from o-hydroxyarylenaminones and Selectfluor was developed at room temperature under catalyst-free conditions. This method showed excellent chemoselectivity and great functional groups tolerance.
- Xu, Jian,Kuang, Zhijie,Song, Qiuling
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supporting information
p. 963 - 966
(2017/11/27)
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- Visible-light-driven, radical-triggered tandem cyclization of o-hydroxyaryl enaminones: Facile access to 3-CF2/CF3-containing chromones
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A practical and straightforward synthetic route to construct a variety of 3-CF2/CF3-containing chromones via photoredox catalysis was developed. This novel protocol features a visible-light-induced radical-triggered tandem cyclizatio
- Xiang, Haoyue,Zhao, Qinglan,Tang, Zhenyu,Xiao, Junan,Xia, Pengju,Wang, Chaoming,Yang, Chunhao,Chen, Xiaoqing,Yang, Hua
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supporting information
p. 146 - 149
(2017/11/27)
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- A facile strategy for accessing 3-alkynylchromones through gold-catalyzed alkynylation/cyclization of o-hydroxyarylenaminones
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A strategy based on tandem alkynylation of o-hydroxyarylenaminones followed by intramolecular cyclization has been developed to generate a diverse array of 3-alkynyl chromones. The functionality embedded in these key intermediates enables their facile elaboration into more diverse structures by a variety of functionalizations and ring-forming processes.
- Akram, Manjur O.,Bera, Saibal,Patil, Nitin T.
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supporting information
p. 12306 - 12309
(2016/10/22)
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- Synthesis of 3-thiophenchromone by stille cross-coupling palladium on charcoal-catalyzed ligand-free
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A new concise, facile, and efficient method for synthesis of 3-thiophenchromone was accomplished in more than over 80% yield starting from formation of the substituted 3-iodochromones and tetrathiophentins by Stille cross-coupling reaction in the presence of palladium on charcoal-catalyzed ligand-free under mild conditions.
- Yang, Qian,Zhang, Zunting,Liang, Bo
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p. 310 - 316
(2015/01/30)
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- First examples of 2,6-diarylnicotinaldehydes prepared under conventional and microwave conditions
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Enaminoketones undergo unexpected self condensation in acetic acid to produce a wide range of 2,3,6-trisubstituted pyridine derivatives in excellent yields in the presence of NH4OAc. This is the first Letter on the synthesis of 2,6-diarylnicoti
- Shankaraiah,Chandrasekhar,Siva Nagi Reddy,Sabitha, Gowravaram
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p. 842 - 846
(2015/03/04)
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- Synthesis, antimycobacterial evaluation and pharmacophore modeling of analogues of the natural product formononetin
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Abstract The synthesis and antimycobacterial activity of formononetin analogues is hereby reported. Formononetin and its analogue 11E showed 88% and 95% growth inhibition, respectively, against the H37Rv strain of Mycobacterium tuberculosis. Pharmacophore modeling studies indicated that the presence of a hydroxyl group in formononetin and its analogues, is crucial for maintaining activity.
- Mutai, Peggoty,Pavadai, Elumalai,Wiid, Ian,Ngwane, Andile,Baker, Bienyameen,Chibale, Kelly
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supporting information
p. 2510 - 2513
(2015/06/02)
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- Synthesis of 4-aminoxanthones by an uncatalyzed, multicomponent reaction
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The synthesis of xanthones via a multicomponent reaction of isocyanides is described for the first time. In this one-pot process, a tandem [4+1] plus [4+2] cycloaddition leads to polysubstituted 4-aminoxanthones in excellent to quantitative yields at room temperature in a non-catalyzed reaction.
- Bornadiego, Ana,Diaz, Jesus,Marcos, Carlos F.
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supporting information
p. 718 - 722
(2014/04/03)
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- A facile and general approach to 3-((trifluoromethyl)thio)-4 H -chromen-4-one
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A facile and efficient synthetic strategy to 3-((trifluoromethyl)thio)-4H-chromen-4-one was developed. AgSCF3 and trichloroisocyanuric acid were employed here to generate active electrophilic trifluoromethylthio species in situ. This reaction could proceed under mild conditions in a short reaction time and be insensitive to air and moisture.
- Xiang, Haoyue,Yang, Chunhao
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supporting information
p. 5686 - 5689
(2015/02/19)
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- Synthesis and biological evaluation of novel pyrazole derivatives with anticancer activity
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We synthesized thirty-six novel pyrazole derivatives and studied their antiproliferative activity in human ovarian adenocarcinoma A2780 cells, human lung carcinoma A549 cells, and murine P388 leukemia cells. Four of these substances were selected because of their higher antiproliferative activity and further analyses showed that they were all able to induce apoptosis, although to a different extent. The expression of p53 and p21waf1, which induce apoptosis and cell cycle arrest, was evaluated by western blot analysis in cells treated with compound 12d. The analysis of the cell cycle showed that all the selected compounds cause a partial G2/M block and the formation of polyploid cells. Furthermore, the four selected compounds were tested for their interaction with the microtubular cytoskeletal system by docking analysis, tubulin polymerization assay and immunofluorescence staining, demonstrating that the compound 12d, unlike the other active derivatives, was able to significantly bind dimers of α- and β-tubulin, probably causing a molecular distortion resulting in the disassembly of microtubules.
- Balbi, Alessandro,Anzaldi, Maria,MacCi, Chiara,Aiello, Cinzia,Mazzei, Mauro,Gangemi, Rosaria,Castagnola, Patrizio,Miele, Mariangela,Rosano, Camillo,Viale, Maurizio
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experimental part
p. 5293 - 5309
(2011/12/14)
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- Synthesis of 2,2′-diaminobischromones using a modified procedure for the rearrangement of 5-(2-hydroxyphenyl)isoxazole to 2-aminochromone
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A modified procedure for the rearrangement of 5-(2-hydroxyphenyl)isoxazoles 6a-e to 2-aminochromones 8a-e was developed and this procedure was utilised in the synthesis of hitherto unreported bischromones 3a-c. The isoxazoles 6a-e were prepared regioselec
- Ghosh, Tarun,Saha, Satyajit,Bandyopadhyay, Chandrakanta
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p. 1845 - 1849
(2007/10/03)
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- 3-Mercaptochromones
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The 3-mercaptochromones 6a-c were synthesized by reduction of the disulfides 4a-c with 2-mercaptoethanol.The compounds 4a-c were prepared from the chromone-3-sulfinic acids 2a-c via the thiosulfonates 3a-c or directly with hydrobromic acid.
- Loewe, Werner,Kennemann, Angela
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p. 239 - 243
(2007/10/02)
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