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Access to 2,3-Disubstituted Benzofurans through One-Pot Acid-Catalyzed Nucleophilic Substitution/TBAF-Mediated Oxacycloisomerization
An efficient synthetic strategy for the synthesis of diversely 2,3‐disubstituted benzofurans is described. This method is based on the use of propargylic alcohols generated from TBS‐protected ortho‐hydroxy benzaldehydes as starting materials and allows a library of 2,3‐disubstituted benzofurans to b...
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| Published in: | European journal of organic chemistry 2012-09, Vol.2012 (27), p.5381-5388 |
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| Main Authors: | , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c4518-c2c7cc5e6cef6d2ac7a8cbfeee5eceb58be52477978f3c6d499fa0fbe37014093 |
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| cites | cdi_FETCH-LOGICAL-c4518-c2c7cc5e6cef6d2ac7a8cbfeee5eceb58be52477978f3c6d499fa0fbe37014093 |
| container_end_page | 5388 |
| container_issue | 27 |
| container_start_page | 5381 |
| container_title | European journal of organic chemistry |
| container_volume | 2012 |
| creator | Raji Reddy, Chada Krishna, Gaddam Kavitha, Nerella Latha, Bellamkonda Shin, Dong-Soo |
| description | An efficient synthetic strategy for the synthesis of diversely 2,3‐disubstituted benzofurans is described. This method is based on the use of propargylic alcohols generated from TBS‐protected ortho‐hydroxy benzaldehydes as starting materials and allows a library of 2,3‐disubstituted benzofurans to be built. The procedure consists of one‐pot nucleophilic substitution, TBS‐deprotection, and exo‐dig cycloisomerization.
A one‐pot method for the synthesis of diversely 2,3‐disubstituted benzofurans from propargylic alcohols is described. The strategy involves acid‐catalyzed nucleophilic substitution followed by TBAF‐mediated desilylative exo‐dig‐oxacycloisomerization. |
| doi_str_mv | 10.1002/ejoc.201200708 |
| format | article |
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A one‐pot method for the synthesis of diversely 2,3‐disubstituted benzofurans from propargylic alcohols is described. The strategy involves acid‐catalyzed nucleophilic substitution followed by TBAF‐mediated desilylative exo‐dig‐oxacycloisomerization.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201200708</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Alkynes ; Chemistry ; Combinatorial chemistry ; Cyclization ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives ; Noncondensed benzenic compounds ; Nucleophilic substitution ; Organic chemistry ; Oxygen heterocycles ; Preparations and properties ; Synthetic methods</subject><ispartof>European journal of organic chemistry, 2012-09, Vol.2012 (27), p.5381-5388</ispartof><rights>Copyright © 2012 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 INIST-CNRS</rights><rights>Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4518-c2c7cc5e6cef6d2ac7a8cbfeee5eceb58be52477978f3c6d499fa0fbe37014093</citedby><cites>FETCH-LOGICAL-c4518-c2c7cc5e6cef6d2ac7a8cbfeee5eceb58be52477978f3c6d499fa0fbe37014093</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=26429385$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Raji Reddy, Chada</creatorcontrib><creatorcontrib>Krishna, Gaddam</creatorcontrib><creatorcontrib>Kavitha, Nerella</creatorcontrib><creatorcontrib>Latha, Bellamkonda</creatorcontrib><creatorcontrib>Shin, Dong-Soo</creatorcontrib><title>Access to 2,3-Disubstituted Benzofurans through One-Pot Acid-Catalyzed Nucleophilic Substitution/TBAF-Mediated Oxacycloisomerization</title><title>European journal of organic chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>An efficient synthetic strategy for the synthesis of diversely 2,3‐disubstituted benzofurans is described. This method is based on the use of propargylic alcohols generated from TBS‐protected ortho‐hydroxy benzaldehydes as starting materials and allows a library of 2,3‐disubstituted benzofurans to be built. The procedure consists of one‐pot nucleophilic substitution, TBS‐deprotection, and exo‐dig cycloisomerization.
A one‐pot method for the synthesis of diversely 2,3‐disubstituted benzofurans from propargylic alcohols is described. The strategy involves acid‐catalyzed nucleophilic substitution followed by TBAF‐mediated desilylative exo‐dig‐oxacycloisomerization.</description><subject>Alkynes</subject><subject>Chemistry</subject><subject>Combinatorial chemistry</subject><subject>Cyclization</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</subject><subject>Noncondensed benzenic compounds</subject><subject>Nucleophilic substitution</subject><subject>Organic chemistry</subject><subject>Oxygen heterocycles</subject><subject>Preparations and properties</subject><subject>Synthetic methods</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><recordid>eNqFkMFv0zAUxiMEEmNw5RwJccOdHTt2fOy6dRsaK4IBu1nOyzN1yeJiJ2LtmT-cVB0VN07vHX7f75O-LHvN6IRRWpzgKsCkoKygVNHqSXbEqNaESk2fjr_ggjDN755nL1JaUUq1lOwo-z0FwJTyPuTFO07OfBrq1Pt-6LHJT7HbBjdE243AMobh-zJfdEg-hj6fgm_IzPa23WxH9GaAFsN66VsP-ee_Dh-6k9vT6Zx8wMbbnXLxYGEDbfAp3GP0W7tjXmbPnG0Tvnq8x9mX-fnt7JJcLy6uZtNrAqJkFYECFECJEtDJprCgbAW1Q8QSAeuyqrEshFJaVY6DbITWzlJXI1eUCar5cfZm713H8HPA1JtVGGI3VhqmpKyYZEKN1GRPQQwpRXRmHf29jRvDqNktbXZLm8PSY-Dto9YmsK0b9wKfDqlCikLzqhw5ved--RY3_7Ga8_eL2b8dZJ_1qceHQ9bGH0Yqrkrz7ebCfPoq7oRicyP5H4Q4oag</recordid><startdate>201209</startdate><enddate>201209</enddate><creator>Raji Reddy, Chada</creator><creator>Krishna, Gaddam</creator><creator>Kavitha, Nerella</creator><creator>Latha, Bellamkonda</creator><creator>Shin, Dong-Soo</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley-VCH</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201209</creationdate><title>Access to 2,3-Disubstituted Benzofurans through One-Pot Acid-Catalyzed Nucleophilic Substitution/TBAF-Mediated Oxacycloisomerization</title><author>Raji Reddy, Chada ; Krishna, Gaddam ; Kavitha, Nerella ; Latha, Bellamkonda ; Shin, Dong-Soo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4518-c2c7cc5e6cef6d2ac7a8cbfeee5eceb58be52477978f3c6d499fa0fbe37014093</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Alkynes</topic><topic>Chemistry</topic><topic>Combinatorial chemistry</topic><topic>Cyclization</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives</topic><topic>Noncondensed benzenic compounds</topic><topic>Nucleophilic substitution</topic><topic>Organic chemistry</topic><topic>Oxygen heterocycles</topic><topic>Preparations and properties</topic><topic>Synthetic methods</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Raji Reddy, Chada</creatorcontrib><creatorcontrib>Krishna, Gaddam</creatorcontrib><creatorcontrib>Kavitha, Nerella</creatorcontrib><creatorcontrib>Latha, Bellamkonda</creatorcontrib><creatorcontrib>Shin, Dong-Soo</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Raji Reddy, Chada</au><au>Krishna, Gaddam</au><au>Kavitha, Nerella</au><au>Latha, Bellamkonda</au><au>Shin, Dong-Soo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Access to 2,3-Disubstituted Benzofurans through One-Pot Acid-Catalyzed Nucleophilic Substitution/TBAF-Mediated Oxacycloisomerization</atitle><jtitle>European journal of organic chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2012-09</date><risdate>2012</risdate><volume>2012</volume><issue>27</issue><spage>5381</spage><epage>5388</epage><pages>5381-5388</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>An efficient synthetic strategy for the synthesis of diversely 2,3‐disubstituted benzofurans is described. This method is based on the use of propargylic alcohols generated from TBS‐protected ortho‐hydroxy benzaldehydes as starting materials and allows a library of 2,3‐disubstituted benzofurans to be built. The procedure consists of one‐pot nucleophilic substitution, TBS‐deprotection, and exo‐dig cycloisomerization.
A one‐pot method for the synthesis of diversely 2,3‐disubstituted benzofurans from propargylic alcohols is described. The strategy involves acid‐catalyzed nucleophilic substitution followed by TBAF‐mediated desilylative exo‐dig‐oxacycloisomerization.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.201200708</doi><tpages>8</tpages></addata></record> |
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| ispartof | European journal of organic chemistry, 2012-09, Vol.2012 (27), p.5381-5388 |
| issn | 1434-193X 1099-0690 |
| language | eng |
| recordid | cdi_proquest_journals_1766816147 |
| source | Wiley-Blackwell Read & Publish Collection |
| subjects | Alkynes Chemistry Combinatorial chemistry Cyclization Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives Noncondensed benzenic compounds Nucleophilic substitution Organic chemistry Oxygen heterocycles Preparations and properties Synthetic methods |
| title | Access to 2,3-Disubstituted Benzofurans through One-Pot Acid-Catalyzed Nucleophilic Substitution/TBAF-Mediated Oxacycloisomerization |
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