An Effective Synthetic Entry to Fused Benzimidazoles via Iodocyclization
A protocol for the synthesis of the fused heterocyclic polycyclic compounds pyrrole[1,2‐a]benzimidazoles, piperidine[1,2‐a]benzimidazoles and oxa‐fused benzimidazoles using iodine and silver nitrate by an exo‐dig or endo‐dig cyclization pathway at room temperature has been developed. Silver nitrate...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2011-06, Vol.353 (9), p.1429-1437 |
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| container_end_page | 1437 |
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| container_issue | 9 |
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| container_title | Advanced synthesis & catalysis |
| container_volume | 353 |
| creator | Zhang, Xu Zhou, Yu Wang, Hengshuai Guo, Diliang Ye, Deju Xu, Yungen Jiang, Hualiang Liu, Hong |
| description | A protocol for the synthesis of the fused heterocyclic polycyclic compounds pyrrole[1,2‐a]benzimidazoles, piperidine[1,2‐a]benzimidazoles and oxa‐fused benzimidazoles using iodine and silver nitrate by an exo‐dig or endo‐dig cyclization pathway at room temperature has been developed. Silver nitrate is a key additive for improving the yield, and the improvement is a result of this additive eliminating the influence of iodine ions (I−), which would otherwise lead to the formation of bis‐iodine by‐products. Cyclizations involving terminal and substituted alkynes were performed. Further functionalizations demonstrated that the iodo derivatives obtained are potential synthetic intermediates that can increase the molecular complexity. |
| doi_str_mv | 10.1002/adsc.201100038 |
| format | Article |
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Silver nitrate is a key additive for improving the yield, and the improvement is a result of this additive eliminating the influence of iodine ions (I−), which would otherwise lead to the formation of bis‐iodine by‐products. Cyclizations involving terminal and substituted alkynes were performed. Further functionalizations demonstrated that the iodo derivatives obtained are potential synthetic intermediates that can increase the molecular complexity.</description><identifier>ISSN: 1615-4150</identifier><identifier>ISSN: 1615-4169</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201100038</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Additives ; Alkynes ; Byproducts ; Chemistry ; cyclization ; Derivatives ; Exact sciences and technology ; fused benzimidazoles ; Heterocyclic compounds ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings ; Iodine ; Organic chemistry ; Preparations and properties ; silver nitrate ; Silver nitrates ; Synthesis ; Terminals</subject><ispartof>Advanced synthesis & catalysis, 2011-06, Vol.353 (9), p.1429-1437</ispartof><rights>Copyright © 2011 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3908-91c58a83150b29899e4a0f980638adf7650db06dba6a7a7d153b52b88a07da113</citedby><cites>FETCH-LOGICAL-c3908-91c58a83150b29899e4a0f980638adf7650db06dba6a7a7d153b52b88a07da113</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fadsc.201100038$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fadsc.201100038$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24302448$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Zhang, Xu</creatorcontrib><creatorcontrib>Zhou, Yu</creatorcontrib><creatorcontrib>Wang, Hengshuai</creatorcontrib><creatorcontrib>Guo, Diliang</creatorcontrib><creatorcontrib>Ye, Deju</creatorcontrib><creatorcontrib>Xu, Yungen</creatorcontrib><creatorcontrib>Jiang, Hualiang</creatorcontrib><creatorcontrib>Liu, Hong</creatorcontrib><title>An Effective Synthetic Entry to Fused Benzimidazoles via Iodocyclization</title><title>Advanced synthesis & catalysis</title><addtitle>Adv. Synth. Catal</addtitle><description>A protocol for the synthesis of the fused heterocyclic polycyclic compounds pyrrole[1,2‐a]benzimidazoles, piperidine[1,2‐a]benzimidazoles and oxa‐fused benzimidazoles using iodine and silver nitrate by an exo‐dig or endo‐dig cyclization pathway at room temperature has been developed. Silver nitrate is a key additive for improving the yield, and the improvement is a result of this additive eliminating the influence of iodine ions (I−), which would otherwise lead to the formation of bis‐iodine by‐products. Cyclizations involving terminal and substituted alkynes were performed. Further functionalizations demonstrated that the iodo derivatives obtained are potential synthetic intermediates that can increase the molecular complexity.</description><subject>Additives</subject><subject>Alkynes</subject><subject>Byproducts</subject><subject>Chemistry</subject><subject>cyclization</subject><subject>Derivatives</subject><subject>Exact sciences and technology</subject><subject>fused benzimidazoles</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</subject><subject>Iodine</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><subject>silver nitrate</subject><subject>Silver nitrates</subject><subject>Synthesis</subject><subject>Terminals</subject><issn>1615-4150</issn><issn>1615-4169</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNqFkL1PwzAQxS0EEqWwMmdBYkk5x0nsjG3pl1TBUBCoi3WxHWFIE4jTQvrXk6pVxcb07qTfe3d6hFxT6FGA4A61U70AaLsAEyekQ2Ma-SGNk9PjHME5uXDuHYBywXmHTPuFN8oyo2q7Md6iKeo3U1vljYq6ary69MZrZ7Q3MMXWrqzGbZkb520serNSl6pRud1ibcvikpxlmDtzddAueR6PnoZTf_44mQ37c1-xBISfUBUJFKz9JA0SkSQmRMgSATETqDMeR6BTiHWKMXLkmkYsjYJUCASukVLWJbf73M-q_FobV8uVdcrkORamXDtJgdFACNFql_T2qKpK5yqTyc_KrrBqWkjuKpO7yuSxstZwc8hGpzDPKiyUdUdXEDIIwnDHJXvu2-am-SdV9u8Xw783_L3Xutr8HL1YfciYMx7Jl4eJjBnQV74cyCX7BcLSiwE</recordid><startdate>201106</startdate><enddate>201106</enddate><creator>Zhang, Xu</creator><creator>Zhou, Yu</creator><creator>Wang, Hengshuai</creator><creator>Guo, Diliang</creator><creator>Ye, Deju</creator><creator>Xu, Yungen</creator><creator>Jiang, Hualiang</creator><creator>Liu, Hong</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley-VCH</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>201106</creationdate><title>An Effective Synthetic Entry to Fused Benzimidazoles via Iodocyclization</title><author>Zhang, Xu ; Zhou, Yu ; Wang, Hengshuai ; Guo, Diliang ; Ye, Deju ; Xu, Yungen ; Jiang, Hualiang ; Liu, Hong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3908-91c58a83150b29899e4a0f980638adf7650db06dba6a7a7d153b52b88a07da113</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Additives</topic><topic>Alkynes</topic><topic>Byproducts</topic><topic>Chemistry</topic><topic>cyclization</topic><topic>Derivatives</topic><topic>Exact sciences and technology</topic><topic>fused benzimidazoles</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</topic><topic>Iodine</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><topic>silver nitrate</topic><topic>Silver nitrates</topic><topic>Synthesis</topic><topic>Terminals</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Xu</creatorcontrib><creatorcontrib>Zhou, Yu</creatorcontrib><creatorcontrib>Wang, Hengshuai</creatorcontrib><creatorcontrib>Guo, Diliang</creatorcontrib><creatorcontrib>Ye, Deju</creatorcontrib><creatorcontrib>Xu, Yungen</creatorcontrib><creatorcontrib>Jiang, Hualiang</creatorcontrib><creatorcontrib>Liu, Hong</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhang, Xu</au><au>Zhou, Yu</au><au>Wang, Hengshuai</au><au>Guo, Diliang</au><au>Ye, Deju</au><au>Xu, Yungen</au><au>Jiang, Hualiang</au><au>Liu, Hong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>An Effective Synthetic Entry to Fused Benzimidazoles via Iodocyclization</atitle><jtitle>Advanced synthesis & catalysis</jtitle><addtitle>Adv. 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Further functionalizations demonstrated that the iodo derivatives obtained are potential synthetic intermediates that can increase the molecular complexity.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/adsc.201100038</doi><tpages>9</tpages></addata></record> |
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| subjects | Additives Alkynes Byproducts Chemistry cyclization Derivatives Exact sciences and technology fused benzimidazoles Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Heterocyclic compounds with only one n hetero atom and condensed derivatives Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Iodine Organic chemistry Preparations and properties silver nitrate Silver nitrates Synthesis Terminals |
| title | An Effective Synthetic Entry to Fused Benzimidazoles via Iodocyclization |
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