Synthesis of 3‑Sulfonylamino Quinolines from 1‑(2-Aminophenyl) Propargyl Alcohols through a Ag(I)-Catalyzed Hydroamination, (2 + 3) Cycloaddition, and an Unusual Strain-Driven Ring Expansion
We describe herein a silver-catalyzed conversion of 1-(2-aminophenyl)-propargyl alcohols to 4-substituted 3-tosylaminoquinolines using TsN3 as an amino surrogate. Controlled reactions reveal the pathway consisting of Ag(I)-catalyzed 5-exo-dig cyclization, catalyst-free (2 + 3) cycloaddition, and ri...
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| Veröffentlicht in: | Organic letters 2015-05, Vol.17 (9), p.2226-2229 |
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| container_title | Organic letters |
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| creator | Kumar, Yalla Kiran Kumar, Gadi Ranjith Reddy, Thota Jagadeshwar Sridhar, Balasubramanian Reddy, Maddi Sridhar |
| description | We describe herein a silver-catalyzed conversion of 1-(2-aminophenyl)-propargyl alcohols to 4-substituted 3-tosylaminoquinolines using TsN3 as an amino surrogate. Controlled reactions reveal the pathway consisting of Ag(I)-catalyzed 5-exo-dig cyclization, catalyst-free (2 + 3) cycloaddition, and ring-expansive rearrangement via nitrogen expulsion. As a support study, we show that the cyclic enamines in similar conditions produce amidines via a C–C bond migration. |
| doi_str_mv | 10.1021/acs.orglett.5b00832 |
| format | Article |
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Controlled reactions reveal the pathway consisting of Ag(I)-catalyzed 5-exo-dig cyclization, catalyst-free (2 + 3) cycloaddition, and ring-expansive rearrangement via nitrogen expulsion. 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Lett</addtitle><description>We describe herein a silver-catalyzed conversion of 1-(2-aminophenyl)-propargyl alcohols to 4-substituted 3-tosylaminoquinolines using TsN3 as an amino surrogate. Controlled reactions reveal the pathway consisting of Ag(I)-catalyzed 5-exo-dig cyclization, catalyst-free (2 + 3) cycloaddition, and ring-expansive rearrangement via nitrogen expulsion. As a support study, we show that the cyclic enamines in similar conditions produce amidines via a C–C bond migration.</description><subject>Alkynes - chemistry</subject><subject>Catalysis</subject><subject>Cyclization</subject><subject>Cycloaddition Reaction</subject><subject>Molecular Structure</subject><subject>Propanols - chemistry</subject><subject>Quinolines - chemical synthesis</subject><subject>Quinolines - chemistry</subject><subject>Silver - chemistry</subject><subject>Sulfhydryl Compounds - chemical synthesis</subject><subject>Sulfhydryl Compounds - chemistry</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kctu1DAUhiMEoqXwBEjoLGcEmfqS63I0FFqpEpeh6-g4cRJXjh3sBBFWvAKvxKPwJHg0Q5csfGwdf_9vHf9R9JKSDSWMXmLtN9Z1Wk7TJhWEFJw9is5pynick5Q9fjhn5Cx65v09ITR0yqfRGUuLPCU5P49-7xcz9dIrD7YF_ufnr_2sW2sWjYMyFj7NoWplpIfW2QFoIFYs3h4ux14Gbg0fnR3RdYuGra5tb7WHqXd27npA2Harm3W8wwn18kM2cL00zh68cVLWvIEVg9fA17Bbam2xadSxjaYJC-7M7GfUsJ8cKhO_deqbNPBZmQ6uvo9ofICfR09a1F6-OO0X0d27qy-76_j2w_ub3fY2Rp6kU4ylyFjTCimKtszzLElqlHlZEyFqITPZFoQmJG2wLmmaiCJ8IZVJ09IEeSHKlF9Eq6Pv6OzXWfqpGpSvpdZopJ19RbM8L0pWUh5QfkRrZ713sq1GpwZ0S0VJdQivCuFVp_CqU3hB9er0wCwG2Txo_qUVgMsjcFDf29mZMO9_Lf8CZDutGw</recordid><startdate>20150501</startdate><enddate>20150501</enddate><creator>Kumar, Yalla Kiran</creator><creator>Kumar, Gadi Ranjith</creator><creator>Reddy, Thota Jagadeshwar</creator><creator>Sridhar, Balasubramanian</creator><creator>Reddy, Maddi Sridhar</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20150501</creationdate><title>Synthesis of 3‑Sulfonylamino Quinolines from 1‑(2-Aminophenyl) Propargyl Alcohols through a Ag(I)-Catalyzed Hydroamination, (2 + 3) Cycloaddition, and an Unusual Strain-Driven Ring Expansion</title><author>Kumar, Yalla Kiran ; Kumar, Gadi Ranjith ; Reddy, Thota Jagadeshwar ; Sridhar, Balasubramanian ; Reddy, Maddi Sridhar</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a345t-a9b62dfbeb8f977644cae79c0bbcbe6ef801405dac9154b80521e4df14a38b953</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Alkynes - chemistry</topic><topic>Catalysis</topic><topic>Cyclization</topic><topic>Cycloaddition Reaction</topic><topic>Molecular Structure</topic><topic>Propanols - chemistry</topic><topic>Quinolines - chemical synthesis</topic><topic>Quinolines - chemistry</topic><topic>Silver - chemistry</topic><topic>Sulfhydryl Compounds - chemical synthesis</topic><topic>Sulfhydryl Compounds - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kumar, Yalla Kiran</creatorcontrib><creatorcontrib>Kumar, Gadi Ranjith</creatorcontrib><creatorcontrib>Reddy, Thota Jagadeshwar</creatorcontrib><creatorcontrib>Sridhar, Balasubramanian</creatorcontrib><creatorcontrib>Reddy, Maddi Sridhar</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kumar, Yalla Kiran</au><au>Kumar, Gadi Ranjith</au><au>Reddy, Thota Jagadeshwar</au><au>Sridhar, Balasubramanian</au><au>Reddy, Maddi Sridhar</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of 3‑Sulfonylamino Quinolines from 1‑(2-Aminophenyl) Propargyl Alcohols through a Ag(I)-Catalyzed Hydroamination, (2 + 3) Cycloaddition, and an Unusual Strain-Driven Ring Expansion</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2015-05-01</date><risdate>2015</risdate><volume>17</volume><issue>9</issue><spage>2226</spage><epage>2229</epage><pages>2226-2229</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>We describe herein a silver-catalyzed conversion of 1-(2-aminophenyl)-propargyl alcohols to 4-substituted 3-tosylaminoquinolines using TsN3 as an amino surrogate. Controlled reactions reveal the pathway consisting of Ag(I)-catalyzed 5-exo-dig cyclization, catalyst-free (2 + 3) cycloaddition, and ring-expansive rearrangement via nitrogen expulsion. As a support study, we show that the cyclic enamines in similar conditions produce amidines via a C–C bond migration.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>25875073</pmid><doi>10.1021/acs.orglett.5b00832</doi><tpages>4</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1523-7060 |
| ispartof | Organic letters, 2015-05, Vol.17 (9), p.2226-2229 |
| issn | 1523-7060 1523-7052 |
| language | eng |
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| source | MEDLINE; American Chemical Society Journals |
| subjects | Alkynes - chemistry Catalysis Cyclization Cycloaddition Reaction Molecular Structure Propanols - chemistry Quinolines - chemical synthesis Quinolines - chemistry Silver - chemistry Sulfhydryl Compounds - chemical synthesis Sulfhydryl Compounds - chemistry |
| title | Synthesis of 3‑Sulfonylamino Quinolines from 1‑(2-Aminophenyl) Propargyl Alcohols through a Ag(I)-Catalyzed Hydroamination, (2 + 3) Cycloaddition, and an Unusual Strain-Driven Ring Expansion |
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