Unexpected results of a SNAr-reaction. A novel synthetic approach to 1-arylthio-2-naphthols
1-(Phenylthio)-3-(pyridin-3-yl)-2-naphthol was obtained as an unexpected result of a nucleophilic aromatic substitution reaction of 3-(pyridine-3-yl)naphthalene-2-yl trifluoromethanesulfonate with thiophenol. This observation led to the discovery of an easy to handle method to synthesize 1-arylthio-...
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| Veröffentlicht in: | Tetrahedron letters 2013-11, Vol.54 (48), p.6615-6618 |
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| creator | Grombein, Cornelia M. Hu, Qingzhong Heim, Ralf Huch, Volker Hartmann, Rolf W. |
| description | 1-(Phenylthio)-3-(pyridin-3-yl)-2-naphthol was obtained as an unexpected result of a nucleophilic aromatic substitution reaction of 3-(pyridine-3-yl)naphthalene-2-yl trifluoromethanesulfonate with thiophenol. This observation led to the discovery of an easy to handle method to synthesize 1-arylthio-2-naphthols. It has been revealed that electron withdrawing groups on the aryl thiol promoted the yields and heterocycle substituents at the 3-position of the naphthalene core are tolerable by the reaction. This reaction can thus serve as a corner stone in the structural diversification of 3-heterocycle substituted 1-arylthio-2-naphthols as potential inhibitors of cytochrome P450. |
| doi_str_mv | 10.1016/j.tetlet.2013.09.111 |
| format | Article |
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This reaction can thus serve as a corner stone in the structural diversification of 3-heterocycle substituted 1-arylthio-2-naphthols as potential inhibitors of cytochrome P450.</description><identifier>ISSN: 0040-4039</identifier><identifier>EISSN: 1873-3581</identifier><identifier>DOI: 10.1016/j.tetlet.2013.09.111</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>1-Arylthio-2-naphthol ; Aromatic compounds ; Corners ; Cytochromes P450 ; Handles ; Inhibitors ; Naphthalene ; SNAr-reaction ; Tetrahedrons ; Thiophenol ; Triflate</subject><ispartof>Tetrahedron letters, 2013-11, Vol.54 (48), p.6615-6618</ispartof><rights>2013 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3001-555099cc387c9c46d9b13fe90cde65619337f6d7fafc9fbb461b5452164b16223</citedby><cites>FETCH-LOGICAL-c3001-555099cc387c9c46d9b13fe90cde65619337f6d7fafc9fbb461b5452164b16223</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.tetlet.2013.09.111$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids></links><search><creatorcontrib>Grombein, Cornelia M.</creatorcontrib><creatorcontrib>Hu, Qingzhong</creatorcontrib><creatorcontrib>Heim, Ralf</creatorcontrib><creatorcontrib>Huch, Volker</creatorcontrib><creatorcontrib>Hartmann, Rolf W.</creatorcontrib><title>Unexpected results of a SNAr-reaction. A novel synthetic approach to 1-arylthio-2-naphthols</title><title>Tetrahedron letters</title><description>1-(Phenylthio)-3-(pyridin-3-yl)-2-naphthol was obtained as an unexpected result of a nucleophilic aromatic substitution reaction of 3-(pyridine-3-yl)naphthalene-2-yl trifluoromethanesulfonate with thiophenol. This observation led to the discovery of an easy to handle method to synthesize 1-arylthio-2-naphthols. It has been revealed that electron withdrawing groups on the aryl thiol promoted the yields and heterocycle substituents at the 3-position of the naphthalene core are tolerable by the reaction. This reaction can thus serve as a corner stone in the structural diversification of 3-heterocycle substituted 1-arylthio-2-naphthols as potential inhibitors of cytochrome P450.</description><subject>1-Arylthio-2-naphthol</subject><subject>Aromatic compounds</subject><subject>Corners</subject><subject>Cytochromes P450</subject><subject>Handles</subject><subject>Inhibitors</subject><subject>Naphthalene</subject><subject>SNAr-reaction</subject><subject>Tetrahedrons</subject><subject>Thiophenol</subject><subject>Triflate</subject><issn>0040-4039</issn><issn>1873-3581</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNp9kD9P5DAUxC3ESSzcfYMrXF7j4Bc7zro5aYX4JyEoYKsrLMd5UbzKxsH2Ivj2Z7TUvOY1M6OZHyG_gVfAQV3uqox5wlzVHETFdQUAJ2QF61Yw0azhlKw4l5xJLvQZOU9px8upNV-Rf9sZ3xd0GXsaMR2mnGgYqKXPj5vIIlqXfZgruqFzeMOJpo85j5i9o3ZZYrBupDlQYDZ-THn0gdVstsuYxzCln-THYKeEv77-BdneXL9c3bGHp9v7q80Dc4JzYE3TcK2dE-vWaSdVrzsQA2ruelSNAi1EO6i-Hezg9NB1UkHXyKYGJTtQdS0uyJ9jbin0esCUzd4nh9NkZwyHZKCVsi17G1Gk8ih1MaQUcTBL9PtS3gA3nyzNzhxZmk-WhmtTWBbb36MNy4w3j9Ek53F22PtY2Jk--O8D_gOWyX6G</recordid><startdate>20131127</startdate><enddate>20131127</enddate><creator>Grombein, Cornelia M.</creator><creator>Hu, Qingzhong</creator><creator>Heim, Ralf</creator><creator>Huch, Volker</creator><creator>Hartmann, Rolf W.</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20131127</creationdate><title>Unexpected results of a SNAr-reaction. 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A novel synthetic approach to 1-arylthio-2-naphthols</atitle><jtitle>Tetrahedron letters</jtitle><date>2013-11-27</date><risdate>2013</risdate><volume>54</volume><issue>48</issue><spage>6615</spage><epage>6618</epage><pages>6615-6618</pages><issn>0040-4039</issn><eissn>1873-3581</eissn><abstract>1-(Phenylthio)-3-(pyridin-3-yl)-2-naphthol was obtained as an unexpected result of a nucleophilic aromatic substitution reaction of 3-(pyridine-3-yl)naphthalene-2-yl trifluoromethanesulfonate with thiophenol. This observation led to the discovery of an easy to handle method to synthesize 1-arylthio-2-naphthols. It has been revealed that electron withdrawing groups on the aryl thiol promoted the yields and heterocycle substituents at the 3-position of the naphthalene core are tolerable by the reaction. 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| ispartof | Tetrahedron letters, 2013-11, Vol.54 (48), p.6615-6618 |
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| language | eng |
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| source | ScienceDirect Journals (5 years ago - present) |
| subjects | 1-Arylthio-2-naphthol Aromatic compounds Corners Cytochromes P450 Handles Inhibitors Naphthalene SNAr-reaction Tetrahedrons Thiophenol Triflate |
| title | Unexpected results of a SNAr-reaction. A novel synthetic approach to 1-arylthio-2-naphthols |
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