One-pot transition-metal-free cascade synthesis of thieno[2,3-c]coumarins from chromones

A one-pot transition-metal-free, base-mediated synthesis of a novel series of functionalized thieno[2,3-c]coumarins via a cascade reaction from chromones has been developed. This cascade reaction involves a Michael addition–Knoevenagel condensation–intramolecular cyclization. This transformation proceeds under mild conditions and gives various thieno[2,3-c]coumarins in good-to-excellent yields. The methodology is tolerant of a wide range of functional groups and applicable to library synthesis.

[1]  R. Singla,et al.  Recent developments of C-4 substituted coumarin derivatives as anticancer agents. , 2016, European journal of medicinal chemistry.

[2]  H. Osman,et al.  Therapeutic potential of coumarins as antiviral agents , 2016, European Journal of Medicinal Chemistry.

[3]  M. Bakthadoss,et al.  One-Pot Synthesis of Benzothiazole-Tethered Chromanones/Coumarins via Claisen Rearrangement Using the Solid State Melt Reaction. , 2016, The Journal of organic chemistry.

[4]  K. Pavelić,et al.  The novel coumarin[3,2-c]thiophene and its hydroxamic acid and ureido derivatives: synthesis and cytostatic activity evaluations , 2016, Medicinal Chemistry Research.

[5]  Yu-Hong Yang,et al.  Synthesis of substituted pyrroles using a silver-catalysed reaction between isocyanoacetates/benzyl isocyanides and chromones , 2015 .

[6]  K. Nakatani,et al.  Exploratory Study on the RNA-Binding Structural Motifs by Library Screening Targeting pre-miRNA-29 a. , 2015, Chemistry.

[7]  Chunfang Jiang,et al.  Cp*Co(III)-Catalyzed Annulations of 2-Alkenylphenols with CO: Mild Access to Coumarin Derivatives. , 2015, Organic letters.

[8]  Chunhao Yang,et al.  Synthesis of multisubstituted 2-aminopyrroles/pyridines via chemoselective Michael addition/intramolecular cyclization reaction. , 2014, Organic letters.

[9]  Z. Miao,et al.  Cascade synthesis of novel functionalized pyridine-fused coumarins in aqueous medium , 2014 .

[10]  Z. Miao,et al.  Rapid access to α-carbolines via a one-pot tandem reaction of α,β-unsaturated ketones with 2-nitrophenylacetonitrile and the anti-proliferative activities of the products. , 2014, Organic & biomolecular chemistry.

[11]  Jayachandran Jayakumar,et al.  One pot synthesis of bioactive benzopyranones through palladium-catalyzed C-H activation and CO insertion into 2-arylphenols. , 2013, Chemical communications.

[12]  Wenchao Yang,et al.  Novel coumarin-based sensitive and selective fluorescent probes for biothiols in aqueous solution and in living cells , 2013 .

[13]  Lin Yuan,et al.  Development of a ratiometric fluorescent pH probe for cell imaging based on a coumarin–quinoline platform , 2013 .

[14]  R. Zaki,et al.  Synthesis and antimicrobial activity of new heterocyclic compounds containing thieno[3,2-c]coumarin and pyrazolo[4,3-c]coumarin frameworks , 2013, Russian Journal of Bioorganic Chemistry.

[15]  Sungwoo Hong,et al.  One-pot catalysis of dehydrogenation of cyclohexanones to phenols and oxidative Heck coupling: expedient synthesis of coumarins. , 2013, Chemical communications.

[16]  J. Nwachukwu,et al.  Thiophene-core estrogen receptor ligands having superagonist activity. , 2013, Journal of medicinal chemistry.

[17]  Chunhao Yang,et al.  Pot, atom and step economic synthesis: a diversity-oriented approach to construct 2-substituted pyrrolo[2,1-f][1,2,4]triazin-4(3H)-ones , 2013 .

[18]  P. Gogoi,et al.  KF/Al2O3/PEG-400: An Efficient Catalytic System for the Fiesselmann-Type Synthesis of Thiophene Derivatives , 2013 .

[19]  P. Langer,et al.  Design and synthesis of condensed thienocoumarins by Suzuki–Miyaura reaction/lactonization tandem protocol , 2012 .

[20]  Chunhao Yang,et al.  One-pot syntheses of novel pyrazole-containing bisphosphonate esters at room temperature. , 2012, Organic & biomolecular chemistry.

[21]  I. Nicholls,et al.  Monitoring the distribution of warfarin in blood plasma. , 2012, ACS medicinal chemistry letters.

[22]  K. Fung,et al.  Anticancer Effects of Imperatorin Isolated from Angelica dahurica: Induction of Apoptosis in HepG2 Cells through both Death-Receptor- and Mitochondria-Mediated Pathways , 2011, Chemotherapy.

[23]  P. Langer,et al.  4-Chloro-3-(trifluoroacetyl)- and 4-chloro-3-(methoxalyl)coumarins as novel and efficient building blocks for the regioselective synthesis of 3,4-fused coumarins , 2011 .

[24]  M. Haukka,et al.  Synthesis and anti-inflammatory effects of a series of novel 7-hydroxycoumarin derivatives. , 2011 .

[25]  C. Shayo,et al.  Coumarins: old compounds with novel promising therapeutic perspectives. , 2010, Current medicinal chemistry.

[26]  Y. Hori,et al.  Photoactive yellow protein-based protein labeling system with turn-on fluorescence intensity. , 2009, Journal of the American Chemical Society.

[27]  G. Melagraki,et al.  Synthesis and evaluation of the antioxidant and anti-inflammatory activity of novel coumarin-3-aminoamides and their alpha-lipoic acid adducts. , 2009, European journal of medicinal chemistry.

[28]  Q. Wang,et al.  7-Diethylamino-3(2'-benzoxazolyl)-coumarin is a novel microtubule inhibitor with antimitotic activity in multidrug resistant cancer cells. , 2009, Biochemical pharmacology.

[29]  V. Snieckus,et al.  Combined directed ortho and remote metalation-Suzuki cross-coupling strategies. Efficient synthesis of heteroaryl-fused benzopyranones from biaryl O-carbamates. , 2009, The Journal of organic chemistry.

[30]  Gang Cheng,et al.  Two efficient cascade reactions to synthesize substituted furocoumarins. , 2008, The Journal of organic chemistry.

[31]  B. Masereel,et al.  Novel 3-carboxamide-coumarins as potent and selective FXIIa inhibitors. , 2008, Journal of medicinal chemistry.

[32]  B. Tyagi,et al.  Synthesis of 7-substituted 4-methyl coumarins by Pechmann reaction using nano-crystalline sulfated-zirconia , 2007 .

[33]  Paul A. Clarke,et al.  Combining pot, atom and step economy (PASE) in organic synthesis. Synthesis of tetrahydropyran-4-ones , 2007 .

[34]  Tomohiro Yamaguchi,et al.  The first total synthesis of lamellarin α 20-sulfate, a selective inhibitor of HIV-1 integrase , 2006 .

[35]  X. Qian,et al.  Detecting Hg2+ ions with an ICT fluorescent sensor molecule: remarkable emission spectra shift and unique selectivity. , 2006, The Journal of organic chemistry.

[36]  J. de Ruyck,et al.  3,6-disubstituted coumarins as mechanism-based inhibitors of thrombin and factor Xa. , 2005, Journal of medicinal chemistry.

[37]  R. Larock,et al.  An efficient synthesis of coumestrol and coumestans by iodocyclization and Pd-catalyzed intramolecular lactonization. , 2005, The Journal of organic chemistry.

[38]  J. Sessler,et al.  Coumarin-strapped calix[4]pyrrole: a fluorogenic anion receptor modulated by cation and anion binding. , 2005, Journal of the American Chemical Society.

[39]  Kelin Li,et al.  Sequential Pd(II)-Pd(0) catalysis for the rapid synthesis of coumarins. , 2005, The Journal of organic chemistry.

[40]  J. Hotchkiss,et al.  Inhibition of 3α-hydroxysteroid dehydrogenase (3α-HSD) activity of human lung microsomes by genistein, daidzein, coumestrol and C18-, C19- and C21-hydroxysteroids and ketosteroids , 2005, Steroids.

[41]  V. Young,et al.  Solid-state properties of warfarin sodium 2-propanol solvate. , 2006, Journal of pharmaceutical sciences.

[42]  F. Havaldar,et al.  A facile synthesis of 10-methoxy-4. 8-dinitro-6H-benzo [2,3-c]chromen-6-one , 2004 .

[43]  G. Röschenthaler,et al.  Synthesis of 2-(trifluoromethyl)-1,2-dihydro-4H-thieno[2,3-c]chromen-4-ones and 2-(trifluoromethyl)-4H-thieno[2,3-c]chromen-4-ones from 2-trifluoromethylchromones and ethyl mercaptoacetate , 2003 .

[44]  I. Vorontsov,et al.  7-Polyfluoroalkylnorkhellins: synthesis and reactions with alkyl mercaptoacetates , 2003 .

[45]  M. Potdar,et al.  Coumarin syntheses via Pechmann condensation in Lewis acidic chloroaluminate ionic liquid , 2001 .

[46]  G. Röschenthaler,et al.  Unexpected synthesis of dihydrothienocoumarin derivatives from 2-trifluoromethylchromones and ethyl mercaptoacetate , 2001 .

[47]  K. Lee,et al.  Chemical constituents of Prangos tschiniganica; structure elucidation and absolute configuration of coumarin and furanocoumarin derivatives with anti-HIV activity. , 2001, Chemical & pharmaceutical bulletin.

[48]  R. Larock,et al.  Synthesis of coumarins via palladium-catalyzed carbonylative annulation of internal alkynes by o-iodophenols , 2000, Organic letters.

[49]  F. Bigi,et al.  Montmorillonite KSF as an Inorganic, Water Stable, and Reusable Catalyst for the Knoevenagel Synthesis of Coumarin-3-carboxylic Acids. , 1999, The Journal of organic chemistry.

[50]  S. Sotheeswaran,et al.  Anti-HIV coumarins from Calophyllum seed oil. , 1998, Bioorganic & medicinal chemistry letters.

[51]  M. D. Mullican,et al.  Novel thiophene-, pyrrole-, furan-, and benzenecarboxamidotetrazoles as potential antiallergy agents. , 1991, Journal of medicinal chemistry.

[52]  S. Patt,et al.  Synthesis and biological properties of thiophene ring analogues of mianserin. , 1983, Journal of medicinal chemistry.

[53]  J. A. Minatelli,et al.  Salicylidene-thiolactone rearrangement. A direct synthesis of 4H-2-arylthieno[3,2-c][1]benzopyran-4-ones , 1977 .