%0 Journal Article %1 ISI:000248202800025 %A Fakhari, Ali Reza %A Nematollahi, Davood %A Shamsipur, Mojtaba %A Makarem, Somayeh %A Davarani, Seyed Saeid Hosseini %A Alizadeh, Abdolali %A Khavasi, Hamid Reza %C THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND %D 2007 %I PERGAMON-ELSEVIER SCIENCE LTD %J TETRAHEDRON %K ECEC acetoacetate; acetoacetate} electrochemical ethyl mechanism; methyl synthesis; voltammetry; {cyclic %N 18 %P 3894-3898 %R 10.1016/j.tet.2007.02.023 %T Electrochemical synthesis of 5,6-dihydroxy-2-methyl-1-benzofuran-3-carboxylate derivatives %V 63 %X Electrochemical oxidation of catechols (1a-c) has been studied in the presence of methyl acetoacetate (2a) and ethyl acetoacetate (2b) as nucleophiles in aqueous solution using cyclic voltammetry and controlled-potential coulometry. The results indicate that the quinones derived from catechols (1a-c) participate in Michael addition reactions with 2a and 2b to form the corresponding benzofuran derivatives (3a-f). The electrochemical synthesis of 3a-f has been successfully performed in an undivided cell in good yield and purity. The oxidation mechanism was deduced from voltammetric data and by coulometry at controlled potential. The products have been characterized after purification by IR, H-1 NMR, C-13 NMR, MS, and single crystal X-ray diffraction. (C) 2007 Elsevier Ltd. All rights reserved.

@article{ISI:000248202800025, abstract = {{Electrochemical oxidation of catechols (1a-c) has been studied in the presence of methyl acetoacetate (2a) and ethyl acetoacetate (2b) as nucleophiles in aqueous solution using cyclic voltammetry and controlled-potential coulometry. The results indicate that the quinones derived from catechols (1a-c) participate in Michael addition reactions with 2a and 2b to form the corresponding benzofuran derivatives (3a-f). The electrochemical synthesis of 3a-f has been successfully performed in an undivided cell in good yield and purity. The oxidation mechanism was deduced from voltammetric data and by coulometry at controlled potential. The products have been characterized after purification by IR, H-1 NMR, C-13 NMR, MS, and single crystal X-ray diffraction. (C) 2007 Elsevier Ltd. All rights reserved.}}, added-at = {2017-05-10T15:29:29.000+0200}, address = {{THE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, ENGLAND}}, affiliation = {{Fakhari, AR (Reprint Author), Shahid Beheshti Univ Med Sci, Fac Sci, Dept Chem, Tehran, Iran. Shahid Beheshti Univ Med Sci, Fac Sci, Dept Chem, Tehran, Iran. Bu Ali Sina Univ, Fac Sci, Dept Chem, Hamadan, Iran. Razi Univ, Fac Sci, Dept Chem, Kermanshah, Iran.}}, author = {Fakhari, Ali Reza and Nematollahi, Davood and Shamsipur, Mojtaba and Makarem, Somayeh and Davarani, Seyed Saeid Hosseini and Alizadeh, Abdolali and Khavasi, Hamid Reza}, author-email = {{a-zavareh@cc.sbu.ac.ir}}, biburl = {https://www.bibsonomy.org/bibtex/265dc5742e5316ddadc9bddb9b27cfa9d/hkhavasi}, cited-references = {{Bard A. J., 2001, ELECTROCHEMICAL METH, P496. BRUN A, 1974, J ELECTROANAL CHEM, V49, P287, DOI 10.1016/S0022-0728(74)80236-6. Cacchi S, 2002, HETEROCYCLES, V56, P613. {*}CAMBR SOFT CORP, CS CHEM DRAW ULTR VE. Fakhari AR, 2005, ELECTROCHIM ACTA, V50, P5322, DOI 10.1016/j.electacta.2005.03.009. Frackenpohl J, 2001, J CHEM SOC PERK T 1, P47, DOI 10.1039/b004693k. Keay B. A., 1996, COMPREHENSIVE HETERO, V2, P395, DOI DOI 10.1016/B978-008096518-5.00047-2. Larock RC, 1998, TETRAHEDRON LETT, V39, P5143, DOI 10.1016/S0040-4039(98)00982-4. Moreno I, 2001, SYNLETT, P1161. MURAE T, 1968, TETRAHEDRON, V24, P2177, DOI 10.1016/0040-4020(68)88119-0. Nematollahi D, 2005, J ORG CHEM, V70, P7769, DOI 10.1021/jo0508301. Nematollahi D, 2005, GREEN CHEM, V7, P638, DOI 10.1039/b503408f. Nematollahi D, 2004, J ORG CHEM, V69, P2637, DOI 10.1021/jo035304t. Nematollahi D, 2004, ELECTROCHIM ACTA, V49, P2495, DOI 10.1016/j.electacta.2004.02.005. Nematollahi D, 2002, J ORG CHEM, V67, P5036, DOI 10.1021/jo0200623. PAPAUCHADO L, 1972, J ELECTROANAL CHEM, V38, P389. PAPOUCHADO L, 1968, J AM CHEM SOC, V90, P5620, DOI 10.1021/ja01022a061. Rayn M. D., 1980, J ELECTROCHEM SOC, V127, P1489. SCHNEIDERS GE, 1979, J ORG CHEM, V44, P4710, DOI 10.1021/jo00393a055. Sun LJ, 1995, J ORG CHEM, V60, P8194, DOI 10.1021/jo00130a018. WARD RS, 1999, NAT PROD REP, V16, P57. YANG Z, 1991, TETRAHEDRON LETT, V32, P2061, DOI 10.1016/S0040-4039(00)78908-8. YOUNG TE, 1974, J ORG CHEM, V39, P1980, DOI 10.1021/jo00927a057. ZANG Y, 2002, J ORG CHEM, V67, P4177.}}, doc-delivery-number = {{192LH}}, doi = {{10.1016/j.tet.2007.02.023}}, interhash = {b7ddca4b25cef57b057f9b30fafe4585}, intrahash = {65dc5742e5316ddadc9bddb9b27cfa9d}, issn = {{0040-4020}}, journal = {{TETRAHEDRON}}, journal-iso = {{Tetrahedron}}, keywords = {ECEC acetoacetate; acetoacetate} electrochemical ethyl mechanism; methyl synthesis; voltammetry; {cyclic}, keywords-plus = {{ELECTROORGANIC SYNTHESIS; BENZOFURAN DERIVATIVES; OXIDATION; CONSTRUCTION; CATECHOLS; HALIDES; ALKYNES}}, language = {{English}}, month = {{APR 30}}, number = {{18}}, number-of-cited-references = {{24}}, pages = {{3894-3898}}, publisher = {{PERGAMON-ELSEVIER SCIENCE LTD}}, research-areas = {{Chemistry}}, times-cited = {{38}}, timestamp = {2017-05-10T15:29:29.000+0200}, title = {{Electrochemical synthesis of 5,6-dihydroxy-2-methyl-1-benzofuran-3-carboxylate derivatives}}, type = {{Article}}, unique-id = {{ISI:000248202800025}}, usage-count-last-180-days = {{1}}, usage-count-since-2013 = {{4}}, volume = {{63}}, web-of-science-categories = {{Chemistry, Organic}}, year = {{2007}} }