A novel, chemoselective one-pot procedure for the preparation of 3H-spiro[isobenzofuran-1,2′-pyrrole]-3,3′(1′H)-dione derivatives via oxidative cleavage of 3a,8b-dihydroxyindeno[1,2-b]pyrroles
A one-pot, efficient and chemoselective procedure for the synthesis of new 3H-spiro[isobenzofuran-1,2′-pyrrole]-3,3′(1′H)-dione derivatives has been developed which involves room temperature oxidative cleavage of 3a,8b-dihydroxyindeno[1,2-b]pyrroles themselves synthesized from the reaction of ninhyd...
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| Published in | Tetrahedron letters Vol. 55; no. 12; pp. 1967 - 1970 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
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19.03.2014
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| Abstract | A one-pot, efficient and chemoselective procedure for the synthesis of new 3H-spiro[isobenzofuran-1,2′-pyrrole]-3,3′(1′H)-dione derivatives has been developed which involves room temperature oxidative cleavage of 3a,8b-dihydroxyindeno[1,2-b]pyrroles themselves synthesized from the reaction of ninhydrin and enaminones in 30% ethanol. A reasonable mechanism is proposed for the oxidation reaction based on the results of this study and our previous related work. |
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| AbstractList | A one-pot, efficient and chemoselective procedure for the synthesis of new 3H-spiro[isobenzofuran-1,2'-pyrrole]-3,3'(1'H) -dione derivatives has been developed which involves room temperature oxidative cleavage of 3a,8b-dihydroxyindeno[1,2-b]pyrroles themselves synthesized from the reaction of ninhydrin and enaminones in 30% ethanol. A reasonable mechanism is proposed for the oxidation reaction based on the results of this study and our previous related work. A one-pot, efficient and chemoselective procedure for the synthesis of new 3H-spiro[isobenzofuran-1,2 '-pyrrole]-3,3 '(1 ' H)-dione derivatives has been developed which involves room temperature oxidative cleavage of 3a,8b-dihydroxyindeno[1,2-b]pyrroles themselves synthesized from the reaction of ninhydrin and enaminones in 30% ethanol. A reasonable mechanism is proposed for the oxidation reaction based on the results of this study and our previous related work. (c) 2014 Elsevier Ltd. All rights reserved. |
| Author | Ariapour, Noushin Alborz, Maryam Mohammadizadeh, Mohammad R. Mahdavinia, Gholam Hossein |
| Author_xml | – sequence: 1 givenname: Gholam Hossein surname: Mahdavinia fullname: Mahdavinia, Gholam Hossein organization: Department of Chemistry, Marvdasht Branch, Islamic Azad University, Marvdasht, Iran – sequence: 2 givenname: Mohammad R. surname: Mohammadizadeh fullname: Mohammadizadeh, Mohammad R. email: mrmohammadizadeh@pgu.ac.ir, mrmohamadizadeh@gmail.com organization: Chemistry Department, Persian Gulf University, Bushehr 75169, Iran – sequence: 3 givenname: Noushin surname: Ariapour fullname: Ariapour, Noushin organization: Chemistry Department, Persian Gulf University, Bushehr 75169, Iran – sequence: 4 givenname: Maryam surname: Alborz fullname: Alborz, Maryam organization: Chemistry Department, Persian Gulf University, Bushehr 75169, Iran |
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| Cites_doi | 10.1016/j.tet.2005.11.011 10.1016/j.tetlet.2010.02.163 10.1016/j.tetlet.2010.08.113 10.1021/ol006050q 10.1016/j.tet.2005.06.026 10.1007/s11239-011-0647-9 10.1016/j.cclet.2010.04.004 10.1016/j.ultsonch.2011.02.007 10.3797/scipharm.1107-02 10.1016/S0040-4039(99)00808-4 10.1021/cr00083a009 10.1039/a709237g 10.1021/jo9915224 10.1002/hlca.200900183 10.1021/cr950257t 10.1016/S0968-0896(00)00061-4 10.1002/hlca.201000241 10.1002/hlca.19950780610 |
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| Snippet | A one-pot, efficient and chemoselective procedure for the synthesis of new 3H-spiro[isobenzofuran-1,2′-pyrrole]-3,3′(1′H)-dione derivatives has been developed... A one-pot, efficient and chemoselective procedure for the synthesis of new 3H-spiro[isobenzofuran-1,2 '-pyrrole]-3,3 '(1 ' H)-dione derivatives has been... A one-pot, efficient and chemoselective procedure for the synthesis of new 3H-spiro[isobenzofuran-1,2'-pyrrole]-3,3'(1'H) -dione derivatives has been developed... |
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| StartPage | 1967 |
| SubjectTerms | Chemistry Chemistry, Organic Chemoselective Cleavage Derivatives Ethanol Ethyl alcohol Indenopyrroles Ninhydrin One-pot Oxidation Oxidative cleavage Physical Sciences Science & Technology Spiroisobenzofuranopyrroles Synthesis Tetrahedrons |
| Title | A novel, chemoselective one-pot procedure for the preparation of 3H-spiro[isobenzofuran-1,2′-pyrrole]-3,3′(1′H)-dione derivatives via oxidative cleavage of 3a,8b-dihydroxyindeno[1,2-b]pyrroles |
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| Volume | 55 |
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