One‐Pot Synthesis of Indolizines Using TBHP as the Methylene Source Under Metal‐Free Condition
An I2/tert‐butyl hydroperoxide (TBHP)‐mediated [2+1+1+1] cycloadditions/oxidative aromatization reactions for the synthesis of indolizines using the one‐pot cascade process have been developed. A variety of aryl methyl ketones react with pyridine/isoquinoline and TBHP in the transition‐metal‐free re...
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| Published in | European journal of organic chemistry Vol. 2020; no. 2; pp. 262 - 266 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
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Wiley
16.01.2020
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| Abstract | An I2/tert‐butyl hydroperoxide (TBHP)‐mediated [2+1+1+1] cycloadditions/oxidative aromatization reactions for the synthesis of indolizines using the one‐pot cascade process have been developed. A variety of aryl methyl ketones react with pyridine/isoquinoline and TBHP in the transition‐metal‐free reaction. This method utilizes readily available starting materials and TBHP acted in this reaction not only as oxidant and radical initiator but also as a methylene source, therefore providing a novel method of atom economy for the synthesis of indolizines.
A novel and simple direct construction of indolizines have been accomplished under metal‐free conditions using the one‐pot cascade process. This new protocol utilizes unfunctionalized starting materials, simple procedures, and successfully introduces the methylene source from TBHP into the indolines. |
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| AbstractList | An I
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tert
‐butyl hydroperoxide (TBHP)‐mediated [2+1+1+1] cycloadditions/oxidative aromatization reactions for the synthesis of indolizines using the one‐pot cascade process have been developed. A variety of aryl methyl ketones react with pyridine/isoquinoline and TBHP in the transition‐metal‐free reaction. This method utilizes readily available starting materials and TBHP acted in this reaction not only as oxidant and radical initiator but also as a methylene source, therefore providing a novel method of atom economy for the synthesis of indolizines. An I-2/tert-butyl hydroperoxide (TBHP)-mediated [2+1+1+1] cycloadditions/oxidative aromatization reactions for the synthesis of indolizines using the one-pot cascade process have been developed. A variety of aryl methyl ketones react with pyridine/isoquinoline and TBHP in the transition-metal-free reaction. This method utilizes readily available starting materials and TBHP acted in this reaction not only as oxidant and radical initiator but also as a methylene source, therefore providing a novel method of atom economy for the synthesis of indolizines. An I2/tert‐butyl hydroperoxide (TBHP)‐mediated [2+1+1+1] cycloadditions/oxidative aromatization reactions for the synthesis of indolizines using the one‐pot cascade process have been developed. A variety of aryl methyl ketones react with pyridine/isoquinoline and TBHP in the transition‐metal‐free reaction. This method utilizes readily available starting materials and TBHP acted in this reaction not only as oxidant and radical initiator but also as a methylene source, therefore providing a novel method of atom economy for the synthesis of indolizines. A novel and simple direct construction of indolizines have been accomplished under metal‐free conditions using the one‐pot cascade process. This new protocol utilizes unfunctionalized starting materials, simple procedures, and successfully introduces the methylene source from TBHP into the indolines. An I2/tert‐butyl hydroperoxide (TBHP)‐mediated [2+1+1+1] cycloadditions/oxidative aromatization reactions for the synthesis of indolizines using the one‐pot cascade process have been developed. A variety of aryl methyl ketones react with pyridine/isoquinoline and TBHP in the transition‐metal‐free reaction. This method utilizes readily available starting materials and TBHP acted in this reaction not only as oxidant and radical initiator but also as a methylene source, therefore providing a novel method of atom economy for the synthesis of indolizines. |
| Author | Zhang, Qianwei Ablajan, Keyume Ma, Huifang Guo, Zhongqi Wang, Bin |
| Author_xml | – sequence: 1 givenname: Qianwei surname: Zhang fullname: Zhang, Qianwei organization: Xinjiang University – sequence: 2 givenname: Keyume orcidid: 0000-0002-3135-6857 surname: Ablajan fullname: Ablajan, Keyume email: ablajan209@hotmail.com organization: Xinjiang University – sequence: 3 givenname: Bin surname: Wang fullname: Wang, Bin organization: Xinjiang University – sequence: 4 givenname: Huifang surname: Ma fullname: Ma, Huifang organization: Xinjiang University – sequence: 5 givenname: Zhongqi surname: Guo fullname: Guo, Zhongqi organization: Xinjiang University |
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| Copyright | 2019 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim 2020 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim |
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| Keywords | Heterocycles Metal-free H BOND CATALYZED ANNULATION DIAZO-COMPOUNDS ALKENES Cycloaddition CINNAMIC-ACIDS Methylene source Multicomponent reactions SUBSTITUTED INDOLIZINES PYRIDINIUM YLIDES C-C BOND ALKYLATION-PEROXIDATION |
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| Score | 2.401233 |
| Snippet | An I2/tert‐butyl hydroperoxide (TBHP)‐mediated [2+1+1+1] cycloadditions/oxidative aromatization reactions for the synthesis of indolizines using the one‐pot... An I-2/tert-butyl hydroperoxide (TBHP)-mediated [2+1+1+1] cycloadditions/oxidative aromatization reactions for the synthesis of indolizines using the one-pot... An I 2 / tert ‐butyl hydroperoxide (TBHP)‐mediated [2+1+1+1] cycloadditions/oxidative aromatization reactions for the synthesis of indolizines using the... |
| Source | Web of Science |
| SourceID | proquest crossref webofscience wiley |
| SourceType | Aggregation Database Enrichment Source Index Database Publisher |
| StartPage | 262 |
| SubjectTerms | Aromatic compounds Butyl hydroperoxide Cascade chemical reactions Chemical synthesis Chemistry Chemistry, Organic Cycloaddition Heterocycles Ketones Metal‐free Methylene Methylene source Multicomponent reactions Oxidizing agents Physical Sciences Science & Technology |
| Title | One‐Pot Synthesis of Indolizines Using TBHP as the Methylene Source Under Metal‐Free Condition |
| URI | https://onlinelibrary.wiley.com/doi/abs/10.1002%2Fejoc.201901803 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000506371100001 https://www.proquest.com/docview/2345498946 |
| Volume | 2020 |
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