Lewis Acid-Catalyzed 1,4-Addition and Annulation of 4-Hydroxy-coumarins with o-Hydroxyphenyl Propargyl Amines: Entry to Regio-Selective Synthesis of Furano[3,2-c]coumarins and Pyrano[3,2-c]coumarins
A facile and regioselective Lewis acid-catalyzed cascade annulation of o-hydroxyphenyl propargyl amines with 4hydroxycoumarin to afford furano[3,2-c]coumarin and pyrano[3,2c]coumarin derivatives is reported. The reaction presumably proceeds by the conjugate addition of 4-hydroxycoumarin to the in si...
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| Veröffentlicht in: | Journal of organic chemistry Jg. 88; H. 7; S. 4730 - 4742 |
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07.04.2023
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| Abstract | A facile and regioselective Lewis acid-catalyzed cascade annulation of o-hydroxyphenyl propargyl amines with 4hydroxycoumarin to afford furano[3,2-c]coumarin and pyrano[3,2c]coumarin derivatives is reported. The reaction presumably proceeds by the conjugate addition of 4-hydroxycoumarin to the in situ-generated alkynyl o-quinone methide and is followed by intramolecular 5-exo-dig and 6-endo-dig annulation to form furano[3,2-c]coumarins and pyrano[3,2-c]coumarins, respectively. The prepared o-hydroxyl substituted pyrano[3,2-c]coumarins could be readily transformed into the corresponding coumarin-derived dioxabicycles by acid-mediated cyclization. |
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| AbstractList | A facile and regioselective Lewis acid-catalyzed cascade annulation of
-hydroxyphenyl propargyl amines with 4-hydroxycoumarin to afford furano[3,2-
]coumarin and pyrano[3,2-
]coumarin derivatives is reported. The reaction presumably proceeds by the conjugate addition of 4-hydroxycoumarin to the in situ-generated alkynyl
-quinone methide and is followed by intramolecular 5-
and 6-
annulation to form furano[3,2-
]coumarins and pyrano[3,2-
]coumarins, respectively. The prepared
-hydroxyl substituted pyrano[3,2-
]coumarins could be readily transformed into the corresponding coumarin-derived dioxabicycles by acid-mediated cyclization. A facile and regioselective Lewis acid-catalyzed cascade annulation of o-hydroxyphenyl propargyl amines with 4hydroxycoumarin to afford furano[3,2-c]coumarin and pyrano[3,2c]coumarin derivatives is reported. The reaction presumably proceeds by the conjugate addition of 4-hydroxycoumarin to the in situ-generated alkynyl o-quinone methide and is followed by intramolecular 5-exo-dig and 6-endo-dig annulation to form furano[3,2-c]coumarins and pyrano[3,2-c]coumarins, respectively. The prepared o-hydroxyl substituted pyrano[3,2-c]coumarins could be readily transformed into the corresponding coumarin-derived dioxabicycles by acid-mediated cyclization. |
| Author | Yang, Ding-Yah Sorabad, Ganesh Shivayogappa |
| Author_xml | – sequence: 1 givenname: Ganesh Shivayogappa surname: Sorabad fullname: Sorabad, Ganesh Shivayogappa organization: Tunghai Univ, Dept Chem, Taichung, Taiwan – sequence: 2 givenname: Ding-Yah orcidid: 0000-0002-3611-2042 surname: Yang fullname: Yang, Ding-Yah email: yang@thu.edu.tw organization: Tunghai Univ, Dept Chem, Taichung, Taiwan |
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| CitedBy_id | crossref_primary_10_1039_D4RA03962A crossref_primary_10_3389_fchem_2024_1362992 crossref_primary_10_1002_adsc_202400893 crossref_primary_10_1002_cbdv_202300836 crossref_primary_10_1016_j_molstruc_2024_139185 |
| Cites_doi | 10.1021/acs.joc.6b00001 10.1021/jo030228f 10.1021/acs.joc.5b00281 10.1021/ar010105m 10.1021/acs.joc.9b01557 10.1007/s00044-011-9810-2 10.1039/c9ob00323a 10.1021/acs.chemrev.9b00145 10.3390/molecules200711733 10.1021/jo400081q 10.1021/ar500330x 10.3762/bjoc.13.53 10.1055/s-2008-1078497 10.1021/jp209925y 10.1021/acs.joc.2c00122 10.1039/c9cc07054k 10.1039/c8ob01927d 10.1021/ol800223g 10.1021/jo201789k 10.1071/CH15267 10.1039/c8cc00671g |
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| Keywords | KETONES CONDENSATION DERIVATIVES QUINONE METHIDES |
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| References | He, XW (WOS:000447018300018) 2018; 16 Appendino, G (WOS:000084519500008) 1999; 62 Shang, YJ (WOS:000354004600057) 2015; 80 Cravotto, G (WOS:000170617300025) 2001; 38 Yi, MH (WOS:000818662400029) 2022; 87 Caruana, L (WOS:000368695400006) 2015; 20 He, XW (WOS:000502728800008) 2019; 55 ARAGNO, M (WOS:A1988M631400009) 1988; 59 Ikawa, M (WOS:000188445800327) 1944; 66 Amouri, H (WOS:000178100400002) 2002; 35 Van de Water, RW (WOS:000176653300001) 2002; 58 Huang, CN (WOS:000258030400016) 2008 Bai, WJ (WOS:000346683200025) 2014; 47 Samanta, S (WOS:000431721000016) 2018; 54 Li, CC (WOS:000186156700027) 2003; 68 Arnone, A (WOS:A1997YD22200003) 1997; 60 He, XW (WOS:000487576900024) 2019; 84 Lei, K (WOS:000367806900015) 2016; 69 He, XW (WOS:000371753900033) 2016; 81 Pathak, TP (WOS:000296754400002) 2011; 76 MICHAEL, JP (WOS:A1995QF64500006) 1995; 12 Ghosh, S (WOS:000396755000001) 2017; 13 Traven, VF (WOS:000254032100071) 2008; 10 Yan, L.-Q. (000961881500001.25) 2021 Yin, GD (WOS:000317327800032) 2013; 78 MOSS, GP (WOS:A1995RP76300002) 1995; 67 Brader, G (WOS:A1996UP39800065) 1996; 42 Nadaraj, V (WOS:000307995200018) 2012; 21 Cao, DX (WOS:000488322600002) 2019; 119 Liu, XG (WOS:000298978000077) 2012; 116 Li, Q. (000961881500001.22) 2019; 361 Yan, LQ (WOS:000466500800014) 2019; 17 |
| References_xml | – volume: 58 start-page: 5367 year: 2002 ident: WOS:000176653300001 article-title: o-quinone methides:: intermediates underdeveloped and underutilized in organic synthesis publication-title: TETRAHEDRON – volume: 81 start-page: 2062 year: 2016 ident: WOS:000371753900033 article-title: FeCl3-Mediated One-Pot Domino Reactions for the Synthesis of 9-Aryl/9-Arylethynyl-2,3,4,9-tetrahydro-1H-xanthen-1-ones from Propargylic Amines/Diaryl Amines and 1,3-Cyclohexanediones publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/acs.joc.6b00001 – volume: 62 start-page: 1627 year: 1999 ident: WOS:000084519500008 article-title: A straightforward entry into polyketide monoprenylated furanocoumarins and pyranocoumarins publication-title: JOURNAL OF NATURAL PRODUCTS – volume: 68 start-page: 8500 year: 2003 ident: WOS:000186156700027 article-title: Total synthesis of wedelolactone publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo030228f – volume: 361 year: 2019 ident: 000961881500001.22 article-title: Base-mediated 1,4-Conjugate Addition/Intramolecular 5- exo-dig Annulation of Propargylamines with Benzoylacetonitriles and /3 -Keto Esters for Polysubstituted Furans and Furo[3,4- c]coumarins Formation publication-title: Adv. Synth. Catal. – volume: 38 start-page: 965 year: 2001 ident: WOS:000170617300025 article-title: "The chemistry of coumarin derivatives".: XII.: A library of pyranocoumarin derivatives via a one-pot three-component hetero Diels-Alder reaction publication-title: JOURNAL OF HETEROCYCLIC CHEMISTRY – volume: 80 start-page: 4760 year: 2015 ident: WOS:000354004600057 article-title: FeCl3-Mediated Synthesis of β-Alkynyl Ketones via Domino Nucleophilic-Substitution/Intramolecular-Cyclization/Reverse Claisen Condensation of N-Cyclohexyl Propargylamines and 1,3-Diketones publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/acs.joc.5b00281 – volume: 35 start-page: 501 year: 2002 ident: WOS:000178100400002 article-title: Taming reactive phenol tautomers and o-quinone methides with transition metals:: A structure-reactivity relationship publication-title: ACCOUNTS OF CHEMICAL RESEARCH doi: 10.1021/ar010105m – volume: 59 start-page: 399 year: 1988 ident: WOS:A1988M631400009 article-title: EXPERIMENTAL STUDIES ON THE TOXICITY OF FERULA-COMMUNIS IN THE RAT publication-title: RESEARCH COMMUNICATIONS IN CHEMICAL PATHOLOGY AND PHARMACOLOGY – volume: 42 start-page: 881 year: 1996 ident: WOS:A1996UP39800065 article-title: Pyranoquinolones and acridones from Vepris bilocularis publication-title: PHYTOCHEMISTRY – volume: 66 start-page: 902 year: 1944 ident: WOS:000188445800327 article-title: Studies on 4-hydroxycoumarins V The condensation of α,β-unsaturated ketones with 4-hydroxycoumarin publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 84 start-page: 11623 year: 2019 ident: WOS:000487576900024 article-title: Catalyst-Free Synthesis of 2,3-Dihydrobenzofurans via a Formal [4+1] Annulation of Propargylamines with Sulfur Ylides publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/acs.joc.9b01557 – volume: 21 start-page: 2902 year: 2012 ident: WOS:000307995200018 article-title: Microwave solvent-free condition synthesis and pharmacological evaluation of pyrano[3,2-c]quinolines publication-title: MEDICINAL CHEMISTRY RESEARCH doi: 10.1007/s00044-011-9810-2 – volume: 67 start-page: 1307 year: 1995 ident: WOS:A1995RP76300002 article-title: GLOSSARY OF CLASS NAMES OF ORGANIC-COMPOUNDS AND REACTIVE INTERMEDIATES BASED ON STRUCTURE publication-title: PURE AND APPLIED CHEMISTRY – volume: 17 start-page: 4005 year: 2019 ident: WOS:000466500800014 article-title: Synthesis of 4-styrylcoumarins via FeCl3-promoted cascade reactions of propargylamines with β-keto esters publication-title: ORGANIC & BIOMOLECULAR CHEMISTRY doi: 10.1039/c9ob00323a – volume: 119 start-page: 10403 year: 2019 ident: WOS:000488322600002 article-title: Coumarin-Based Small-Molecule Fluorescent Chemosensors publication-title: CHEMICAL REVIEWS doi: 10.1021/acs.chemrev.9b00145 – volume: 20 start-page: 11733 year: 2015 ident: WOS:000368695400006 article-title: The Emergence of Quinone Methides in Asymmetric Organocatalysis publication-title: MOLECULES doi: 10.3390/molecules200711733 – volume: 78 start-page: 3132 year: 2013 ident: WOS:000317327800032 article-title: Stereoselective Synthesis of 2,8-Dioxabicyclo[3.3.1]nonane Derivatives via a Sequential Michael Addition/Bicyclization Reaction publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo400081q – volume: 47 start-page: 3655 year: 2014 ident: WOS:000346683200025 article-title: The Domestication of ortho-Quinone Methides publication-title: ACCOUNTS OF CHEMICAL RESEARCH doi: 10.1021/ar500330x – volume: 60 start-page: 971 year: 1997 ident: WOS:A1997YD22200003 article-title: Constituents of Dragon's Blood .5. Dracoflavans B-1, B-2, C-1, C-2, D-1, and D-2, new A-type deoxyproanthocyanidins publication-title: JOURNAL OF NATURAL PRODUCTS – volume: 12 start-page: 77 year: 1995 ident: WOS:A1995QF64500006 article-title: QUINOLINE, QUINAZOLINE, AND ACRIDONE ALKALOIDS publication-title: NATURAL PRODUCT REPORTS – volume: 13 start-page: 552 year: 2017 ident: WOS:000396755000001 article-title: Effect of the ortho-hydroxy group of salicylaldehyde in the A3 coupling reaction: A metal-catalyst-free synthesis of propargylamine publication-title: BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY doi: 10.3762/bjoc.13.53 – start-page: 1825 year: 2008 ident: WOS:000258030400016 article-title: Synthesis, characterization, and redox property of 3-(2-phenyl-4H-thiochromen-4-ylidene)-3H-chromene-2,4-diones publication-title: SYNLETT doi: 10.1055/s-2008-1078497 – volume: 116 start-page: 727 year: 2012 ident: WOS:000298978000077 article-title: Molecular Origins of Optoelectronic Properties in Coumarin Dyes: Toward Designer Solar Cell and Laser Applications publication-title: JOURNAL OF PHYSICAL CHEMISTRY A doi: 10.1021/jp209925y – volume: 87 start-page: 5795 year: 2022 ident: WOS:000818662400029 article-title: Copper-Catalyzed Cascade Annulation of o-HydroxyphenylPropargylamines with Pyrazolin-5-ones to AccessPyrano[2,3-c]pyrazoles publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/acs.joc.2c00122 – volume: 55 start-page: 15069 year: 2019 ident: WOS:000502728800008 article-title: A ZnI2-catalyzed regioselective cascade 1,4-conjugate addition/5-exo-dig annulation pathway for one-pot access to heterobiaryl frameworks publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c9cc07054k – volume: 16 start-page: 7191 year: 2018 ident: WOS:000447018300018 article-title: FeCl3-promoted tandem 1,4-conjugate addition/6-endo-dig cyclization/oxidation of propargylamines and benzoylacetonitriles/malononitriles: direct access to functionalized 2-aryl-4H-chromenes publication-title: ORGANIC & BIOMOLECULAR CHEMISTRY doi: 10.1039/c8ob01927d – volume: 10 start-page: 1319 year: 2008 ident: WOS:000254032100071 article-title: Coumarinyl(thienyl)thiazoles: Novel photochromes with modulated fluorescence publication-title: ORGANIC LETTERS doi: 10.1021/ol800223g – volume: 76 start-page: 9210 year: 2011 ident: WOS:000296754400002 article-title: Applications of ortho-Quinone Methide Intermediates in Catalysis and Asymmetric Synthesis publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo201789k – volume: 69 start-page: 98 year: 2016 ident: WOS:000367806900015 article-title: A New Protocol for Total Synthesis of Natural Product Frutinone A and Its Derivatives publication-title: AUSTRALIAN JOURNAL OF CHEMISTRY doi: 10.1071/CH15267 – volume: 54 start-page: 3379 year: 2018 ident: WOS:000431721000016 article-title: Regioselective synthesis of unsymmetrical biheteroaryls via copper(II)-catalyzed cascade annulation publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c8cc00671g – year: 2021 ident: 000961881500001.25 article-title: Copper-Catalyzed Cascade 1,4-Addition/Annulation/ Hydrolysis of Propargylamines with 2-Hydroxynaphthalene-1,4-diones: Direct Formation of 12-Phenacyl-11H-benzo[b]xanthenes publication-title: J. Org. Chem. |
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| Snippet | A facile and regioselective Lewis acid-catalyzed cascade annulation of o-hydroxyphenyl propargyl amines with 4hydroxycoumarin to afford furano[3,2-c]coumarin... A facile and regioselective Lewis acid-catalyzed cascade annulation of -hydroxyphenyl propargyl amines with 4-hydroxycoumarin to afford furano[3,2- ]coumarin... |
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| Title | Lewis Acid-Catalyzed 1,4-Addition and Annulation of 4-Hydroxy-coumarins with o-Hydroxyphenyl Propargyl Amines: Entry to Regio-Selective Synthesis of Furano[3,2-c]coumarins and Pyrano[3,2-c]coumarins |
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