Cu (I) Catalyzed One Pot S-N-Click Reactions of Halogenated Coumarins and 1-aza-coumarins
A one pot three component, copper catalyzed azide-alkyne cycloaddition reaction has been employed for the synthesis of bis-coumarinyl triazoles (A-D) using 4-chloro, 4-bromomethyl, 3-bromoacetyl and 4-bromomethyl-1-aza-coumarins (I-IV), sodium azide, and coumarin propargyl ethers (V-IX) in moderate...
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| Published in | Journal of heterocyclic chemistry Vol. 55; no. 2; pp. 537 - 544 |
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| Main Authors | , |
| Format | Journal Article |
| Language | English |
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| Abstract | A one pot three component, copper catalyzed azide-alkyne cycloaddition reaction has been employed for the synthesis of bis-coumarinyl triazoles (A-D) using 4-chloro, 4-bromomethyl, 3-bromoacetyl and 4-bromomethyl-1-aza-coumarins (I-IV), sodium azide, and coumarin propargyl ethers (V-IX) in moderate yields. |
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| AbstractList | A one pot three component, copper catalyzed azide-alkyne cycloaddition reaction has been employed for the synthesis of bis-coumarinyl triazoles (A-D) using 4-chloro, 4-bromomethyl, 3-bromoacetyl and 4-bromomethyl-1-aza-coumarins (I-IV), sodium azide, and coumarin propargyl ethers (V-IX) in moderate yields. A one pot three component, copper catalyzed azide‐alkyne cycloaddition reaction has been employed for the synthesis of bis ‐coumarinyl triazoles ( A – D ) using 4‐chloro, 4‐bromomethyl, 3‐bromoacetyl and 4‐bromomethyl‐1‐ aza ‐coumarins ( I – IV ), sodium azide, and coumarin propargyl ethers ( V – IX ) in moderate yields. |
| Author | Kulkarni, Manohar V. Revankar, Hrishikesh M. |
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| Cites_doi | 10.1021/ol0621506 10.1021/jo200085j 10.1016/j.tet.2009.03.035 10.1039/c2gc36521a 10.1016/j.tet.2012.07.080 10.1021/jo1024927 10.1021/ol1022036 10.1021/ol048341v 10.1111/j.1747-0285.2012.01441.x 10.1021/jo2016339 10.1021/co1000234 10.1021/jo500890w 10.1080/00397911.2013.833628 10.1021/jo01070a042 10.1139/v68-409 10.1039/b919434g 10.1080/00397919008244901 10.1002/ardp.19813140810 10.1002/ardp.19662990513 10.1039/C2GC36521A |
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| Keywords | CYCLOADDITION ALKYNES AZIDE ACIDS 1,2,3-TRIAZOLES |
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| References | Kolarovic, A (WOS:000289187300023) 2011; 76 RAO, CP (WOS:A1990CV83800007) 1990; 20 Alonso, F (WOS:000295816700027) 2011; 76 Lal, S (WOS:000288692000056) 2011; 76 Naik, RJ (WOS:000308994500003) 2012; 80 Li, WT (WOS:000288062600012) 2011; 13 Friscourt, F (WOS:000283531000059) 2010; 12 Mohammed, S (WOS:000308451500003) 2012; 68 Beckmann, HSG (WOS:000243124900001) 2007; 9 Rao,, C. P. (000424271200020.19) 1000; 30 Mishra, KB (WOS:000337871100037) 2014; 79 Verduyn,, L. S. C. (000424271200020.22) 2010; 46 KULKARNI, MV (WOS:A1981MC43700009) 1981; 314 KNIGHT, AR (WOS:A1968B640000004) 1968; 46 Mukherjee, N (WOS:000314185900016) 2013; 15 Sehulte,, K. E. (000424271200020.21) 1966; 299 COOK, DJ (WOS:A19616263B00026) 1961; 26 Rao,, C. P. (000424271200020.17) 1000; 33 Appukkuttan, P (WOS:000224973100022) 2004; 6 Dururgkar, KA (WOS:000265962600005) 2009; 65 Espinosa,, D. M. (000424271200020.6) 2014; 44 RAO, VR (WOS:A1986C215900019) 1986; 25 e_1_2_7_6_1 Sehulte K. E. (e_1_2_7_19_1) 1966; 299 e_1_2_7_5_1 e_1_2_7_4_1 e_1_2_7_3_1 e_1_2_7_9_1 e_1_2_7_8_1 e_1_2_7_7_1 Kolarovi A. (e_1_2_7_12_1) 2011; 76 e_1_2_7_18_1 e_1_2_7_16_1 Rao C. P. (e_1_2_7_22_1); 33 e_1_2_7_2_1 e_1_2_7_15_1 Rao C. P. (e_1_2_7_21_1); 30 Rao R. V. (e_1_2_7_17_1) 1986; 25 e_1_2_7_13_1 Mishra K. B. (e_1_2_7_14_1) 2014; 78 e_1_2_7_23_1 e_1_2_7_10_1 e_1_2_7_20_1 Verduyn L. S. C. (e_1_2_7_11_1) 2010; 46 |
| References_xml | – volume: 9 start-page: 1 year: 2007 ident: WOS:000243124900001 article-title: One-pot procedure for diazo transfer and azide-alkyne cycloaddition: Triazole linkages from amines publication-title: ORGANIC LETTERS doi: 10.1021/ol0621506 contributor: fullname: Beckmann, HSG – volume: 76 start-page: 2367 year: 2011 ident: WOS:000288692000056 article-title: [CuBr(PPh3)(3)] for Azide-Allkyne Cycloaddition Reactions under Strict Click Conditions publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo200085j contributor: fullname: Lal, S – volume: 26 start-page: 4949 year: 1961 ident: WOS:A19616263B00026 article-title: BROMINATION STUDIES OF ALKYL-SUBSTITUTED 2-PYRIDONES AND 2-QUINOLONES publication-title: JOURNAL OF ORGANIC CHEMISTRY contributor: fullname: COOK, DJ – volume: 65 start-page: 3974 year: 2009 ident: WOS:000265962600005 article-title: A Cu(I)-promoted one-pot 'SNAr-click reaction' of fluoronitrobenzenes publication-title: TETRAHEDRON doi: 10.1016/j.tet.2009.03.035 contributor: fullname: Dururgkar, KA – volume: 15 start-page: 389 year: 2013 ident: WOS:000314185900016 article-title: Solvent-free one-pot synthesis of 1,2,3-triazole derivatives by the 'Click' reaction of alkyl halides or aryl boronic acids, sodium azide and terminal alkynes over a Cu/Al2O3 surface under ball-milling publication-title: GREEN CHEMISTRY doi: 10.1039/c2gc36521a contributor: fullname: Mukherjee, N – volume: 46 start-page: 2495 year: 1968 ident: WOS:A1968B640000004 article-title: ISOLATION AND CHARACTERIZATION OF 4-CHLORO-3,4' - 3',4''-TERCOUMARIN publication-title: CANADIAN JOURNAL OF CHEMISTRY contributor: fullname: KNIGHT, AR – volume: 68 start-page: 8156 year: 2012 ident: WOS:000308451500003 article-title: Recyclable clay supported Cu (II) catalyzed tandem one-pot synthesis of 1-aryl-1,2,3-triazoles publication-title: TETRAHEDRON doi: 10.1016/j.tet.2012.07.080 contributor: fullname: Mohammed, S – volume: 33 start-page: 593 year: 1000 ident: 000424271200020.17 publication-title: Indian J Chem B contributor: fullname: Rao,, C. P. – volume: 25 start-page: 413 year: 1986 ident: WOS:A1986C215900019 article-title: STUDIES ON COUMARIN DERIVATIVES .1. SYNTHESIS OF SOME SUBSTITUTED THIAZOLYL-COUMARINS AND BENZOXAZINYL-COUMARINS publication-title: INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY contributor: fullname: RAO, VR – volume: 76 start-page: 2613 year: 2011 ident: WOS:000289187300023 article-title: Tandem Catalysis: From Alkynoic Acids and Aryl Iodides to 1,2,3-Triazoles in One Pot publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo1024927 contributor: fullname: Kolarovic, A – volume: 12 start-page: 4936 year: 2010 ident: WOS:000283531000059 article-title: One-Pot Three-Step Synthesis of 1,2,3-Triazoles by Copper-Catalyzed Cycloaddition of Azides with Alkynes formed by a Sonogashira Cross-Coupling and Desilylation publication-title: ORGANIC LETTERS doi: 10.1021/ol1022036 contributor: fullname: Friscourt, F – volume: 6 start-page: 4223 year: 2004 ident: WOS:000224973100022 article-title: A microwave-assisted click chemistry synthesis of 1,4-disubstituted 1,2,3-triazoles via a copper(I)-catalyzed three-component reaction publication-title: ORGANIC LETTERS doi: 10.1021/ol048341v contributor: fullname: Appukkuttan, P – volume: 46 start-page: 898 year: 2010 ident: 000424271200020.22 publication-title: Chem Comm contributor: fullname: Verduyn,, L. S. C. – volume: 30 start-page: 666 year: 1000 ident: 000424271200020.19 publication-title: Indian J Chem B contributor: fullname: Rao,, C. P. – volume: 299 start-page: 457 year: 1966 ident: 000424271200020.21 publication-title: Arch Pharm contributor: fullname: Sehulte,, K. E. – volume: 80 start-page: 516 year: 2012 ident: WOS:000308994500003 article-title: Click Chemistry Approach for Bis-Chromenyl Triazole Hybrids and Their Antitubercular Activity publication-title: CHEMICAL BIOLOGY & DRUG DESIGN doi: 10.1111/j.1747-0285.2012.01441.x contributor: fullname: Naik, RJ – volume: 44 start-page: 807 year: 2014 ident: 000424271200020.6 publication-title: Synth Comm contributor: fullname: Espinosa,, D. M. – volume: 314 start-page: 708 year: 1981 ident: WOS:A1981MC43700009 article-title: STUDIES ON COUMARINS .1. publication-title: ARCHIV DER PHARMAZIE contributor: fullname: KULKARNI, MV – volume: 20 start-page: 535 year: 1990 ident: WOS:A1990CV83800007 article-title: CLAISEN REARRANGEMENT OF 4-PROPARGYLOXYCOUMARINS - FORMATION OF 2H,5H-PYRANO[3,2-C][1]BENZOPYRAN-5-ONES publication-title: SYNTHETIC COMMUNICATIONS contributor: fullname: RAO, CP – volume: 76 start-page: 8394 year: 2011 ident: WOS:000295816700027 article-title: Multicomponent Click Synthesis of 1,2,3-Triazoles from Epoxides in Water Catalyzed by Copper Nanoparticles on Activated Carbons publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo2016339 contributor: fullname: Alonso, F – volume: 13 start-page: 72 year: 2011 ident: WOS:000288062600012 article-title: One-Pot Tandem Copper-Catalyzed Library Synthesis of 1-Thiazolyl-1,2,3-triazoles as Anticancer Agents publication-title: ACS COMBINATORIAL SCIENCE doi: 10.1021/co1000234 contributor: fullname: Li, WT – volume: 79 start-page: 5752 year: 2014 ident: WOS:000337871100037 article-title: Click Chemistry Inspired Synthesis of Morpholine-Fused Triazoles publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo500890w contributor: fullname: Mishra, KB – ident: e_1_2_7_9_1 doi: 10.1021/co1000234 – ident: e_1_2_7_10_1 doi: 10.1080/00397911.2013.833628 – ident: e_1_2_7_18_1 doi: 10.1021/jo01070a042 – ident: e_1_2_7_23_1 doi: 10.1111/j.1747-0285.2012.01441.x – ident: e_1_2_7_6_1 doi: 10.1016/j.tet.2012.07.080 – ident: e_1_2_7_15_1 doi: 10.1139/v68-409 – volume: 25 start-page: 413 year: 1986 ident: e_1_2_7_17_1 publication-title: Indian J Chem contributor: fullname: Rao R. V. – volume: 46 start-page: 898 year: 2010 ident: e_1_2_7_11_1 publication-title: Chem Comm doi: 10.1039/b919434g contributor: fullname: Verduyn L. S. C. – ident: e_1_2_7_20_1 doi: 10.1080/00397919008244901 – ident: e_1_2_7_16_1 doi: 10.1002/ardp.19813140810 – ident: e_1_2_7_4_1 doi: 10.1021/jo200085j – ident: e_1_2_7_7_1 doi: 10.1016/j.tet.2009.03.035 – volume: 299 start-page: 457 year: 1966 ident: e_1_2_7_19_1 publication-title: Arch Pharm doi: 10.1002/ardp.19662990513 contributor: fullname: Sehulte K. E. – volume: 78 start-page: 5752 year: 2014 ident: e_1_2_7_14_1 publication-title: J. Org Chem doi: 10.1021/jo500890w contributor: fullname: Mishra K. B. – volume: 33 start-page: 593 ident: e_1_2_7_22_1 publication-title: Indian J Chem contributor: fullname: Rao C. P. – volume: 76 start-page: 2613 year: 2011 ident: e_1_2_7_12_1 publication-title: J. Org Chem doi: 10.1021/jo1024927 contributor: fullname: Kolarovi A. – ident: e_1_2_7_2_1 doi: 10.1021/ol048341v – ident: e_1_2_7_13_1 doi: 10.1021/ol0621506 – volume: 30 start-page: 666 ident: e_1_2_7_21_1 publication-title: Indian J Chem contributor: fullname: Rao C. P. – ident: e_1_2_7_5_1 doi: 10.1039/C2GC36521A – ident: e_1_2_7_3_1 doi: 10.1021/jo2016339 – ident: e_1_2_7_8_1 doi: 10.1021/ol1022036 |
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| Snippet | A one pot three component, copper catalyzed azide-alkyne cycloaddition reaction has been employed for the synthesis of bis-coumarinyl triazoles (A-D) using... A one pot three component, copper catalyzed azide‐alkyne cycloaddition reaction has been employed for the synthesis of bis ‐coumarinyl triazoles ( A – D )... |
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| Title | Cu (I) Catalyzed One Pot S-N-Click Reactions of Halogenated Coumarins and 1-aza-coumarins |
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