Catalyst-Driven Scaffold Diversity: Selective Synthesis of Spirocycles, Carbazoles and Quinolines from Indolyl Ynones
Medicinally relevant spirocyclic indolenines, carbazoles and quinolines can each be directly synthesised selectively from common indolyl ynone starting materials by catalyst variation. The high yielding, divergent reactions all proceed by an initial dearomatising spirocyclisation reaction to generat...
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| Veröffentlicht in: | Chemistry : a European journal 2016-06, Vol.22 (26), p.8777-8780 |
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| container_title | Chemistry : a European journal |
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| creator | Liddon, John T. R. James, Michael J. Clarke, Aimee K. O'Brien, Peter Taylor, Richard J. K. Unsworth, William P. |
| description | Medicinally relevant spirocyclic indolenines, carbazoles and quinolines can each be directly synthesised selectively from common indolyl ynone starting materials by catalyst variation. The high yielding, divergent reactions all proceed by an initial dearomatising spirocyclisation reaction to generate an intermediate vinyl–metal species, which then rearranges selectively by careful choice of catalyst and reaction conditions.
Medicinally relevant spirocyclic indolenines, carbazoles and quinolines can each be directly synthesised selectively from common indolyl ynone starting materials by catalyst variation (see scheme). The high yielding, divergent reactions all proceed by an initial dearomatising spirocyclisation reaction to generate an intermediate vinyl–metal species, which then rearranges selectively by careful choice of catalyst and reaction conditions. |
| doi_str_mv | 10.1002/chem.201601836 |
| format | Article |
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Medicinally relevant spirocyclic indolenines, carbazoles and quinolines can each be directly synthesised selectively from common indolyl ynone starting materials by catalyst variation (see scheme). The high yielding, divergent reactions all proceed by an initial dearomatising spirocyclisation reaction to generate an intermediate vinyl–metal species, which then rearranges selectively by careful choice of catalyst and reaction conditions.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201601836</identifier><identifier>PMID: 27124236</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>Carbazoles ; Carbazoles - chemical synthesis ; Carbazoles - chemistry ; Catalysis ; Catalysts ; Chemical synthesis ; Chemistry ; Communication ; Communications ; diversity ; Indoles - chemistry ; Materials selection ; Mesylates - chemistry ; Metals ; Organic compounds ; Quinolines ; Quinolines - chemical synthesis ; Quinolines - chemistry ; Scaffolds ; Spiro Compounds - chemical synthesis ; Spiro Compounds - chemistry ; spirocycles ; Stereoisomerism ; Synthesis</subject><ispartof>Chemistry : a European journal, 2016-06, Vol.22 (26), p.8777-8780</ispartof><rights>2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c6706-f6d1c8c2dea1cf947edbf3424c9120df95edc2cc4cb4cb34bb867d5f10d291f03</citedby><cites>FETCH-LOGICAL-c6706-f6d1c8c2dea1cf947edbf3424c9120df95edc2cc4cb4cb34bb867d5f10d291f03</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%2Fchem.201601836$$EPDF$$P50$$Gwiley$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201601836$$EHTML$$P50$$Gwiley$$Hfree_for_read</linktohtml><link.rule.ids>230,314,776,780,881,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27124236$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Liddon, John T. R.</creatorcontrib><creatorcontrib>James, Michael J.</creatorcontrib><creatorcontrib>Clarke, Aimee K.</creatorcontrib><creatorcontrib>O'Brien, Peter</creatorcontrib><creatorcontrib>Taylor, Richard J. K.</creatorcontrib><creatorcontrib>Unsworth, William P.</creatorcontrib><title>Catalyst-Driven Scaffold Diversity: Selective Synthesis of Spirocycles, Carbazoles and Quinolines from Indolyl Ynones</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>Medicinally relevant spirocyclic indolenines, carbazoles and quinolines can each be directly synthesised selectively from common indolyl ynone starting materials by catalyst variation. The high yielding, divergent reactions all proceed by an initial dearomatising spirocyclisation reaction to generate an intermediate vinyl–metal species, which then rearranges selectively by careful choice of catalyst and reaction conditions.
Medicinally relevant spirocyclic indolenines, carbazoles and quinolines can each be directly synthesised selectively from common indolyl ynone starting materials by catalyst variation (see scheme). The high yielding, divergent reactions all proceed by an initial dearomatising spirocyclisation reaction to generate an intermediate vinyl–metal species, which then rearranges selectively by careful choice of catalyst and reaction conditions.</description><subject>Carbazoles</subject><subject>Carbazoles - chemical synthesis</subject><subject>Carbazoles - chemistry</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Chemical synthesis</subject><subject>Chemistry</subject><subject>Communication</subject><subject>Communications</subject><subject>diversity</subject><subject>Indoles - chemistry</subject><subject>Materials selection</subject><subject>Mesylates - chemistry</subject><subject>Metals</subject><subject>Organic compounds</subject><subject>Quinolines</subject><subject>Quinolines - chemical synthesis</subject><subject>Quinolines - chemistry</subject><subject>Scaffolds</subject><subject>Spiro Compounds - chemical synthesis</subject><subject>Spiro Compounds - chemistry</subject><subject>spirocycles</subject><subject>Stereoisomerism</subject><subject>Synthesis</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>EIF</sourceid><recordid>eNqFks1vFCEYxonR2HX16tGQePHgVD4GmPFgYra1bdLWmK2ueiEMAy4tO6wwUx3_etls3VQPNiGBF37Pk7wvDwBPMdrHCJFXemlW-wRhjnBF-T0wwYzgggrO7oMJqktRcEbrPfAopUuEUM0pfQj2iMCkJJRPwDBTvfJj6ouD6K5NB-daWRt8Cw9yGZPrx9dwbrzRfa7hfOz6pUkuwWDhfO1i0KP2Jr2EMxUb9SvkM1RdCz8Mrgvedbm0MazgSdcGP3r4pQv57jF4YJVP5snNPgUf3x1ezI6L0_dHJ7O3p4XmAvHC8hbrSpPWKKxtbsa0jaUlKXWNCWptzUyridalbvKiZdNUXLTMYtSSGltEp-DN1nc9NKvMmq6Pyst1dCsVRxmUk3-_dG4pv4VryVBVClZmgxc3BjF8H0zq5colbbxXnQlDkrgijCGECb0bFbWoBMN04_r8H_QyDLHLk5C4RoIxjgj_LyVqLnhd5T-cgv0tpWNIKRq76w4juYmI3ERE7iKSBc9uz2SH_8lEBuot8MN5M95hJ2fHh2e3zYut1qXe_NxpVbySXFDB5OL8SC4-XSzOF2ef5Vf6GwMN2dU</recordid><startdate>20160620</startdate><enddate>20160620</enddate><creator>Liddon, John T. R.</creator><creator>James, Michael J.</creator><creator>Clarke, Aimee K.</creator><creator>O'Brien, Peter</creator><creator>Taylor, Richard J. K.</creator><creator>Unsworth, William P.</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><general>John Wiley and Sons Inc</general><scope>BSCLL</scope><scope>24P</scope><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>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>20160620</creationdate><title>Catalyst-Driven Scaffold Diversity: Selective Synthesis of Spirocycles, Carbazoles and Quinolines from Indolyl Ynones</title><author>Liddon, John T. R. ; James, Michael J. ; Clarke, Aimee K. ; O'Brien, Peter ; Taylor, Richard J. 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R.</creatorcontrib><creatorcontrib>James, Michael J.</creatorcontrib><creatorcontrib>Clarke, Aimee K.</creatorcontrib><creatorcontrib>O'Brien, Peter</creatorcontrib><creatorcontrib>Taylor, Richard J. 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The high yielding, divergent reactions all proceed by an initial dearomatising spirocyclisation reaction to generate an intermediate vinyl–metal species, which then rearranges selectively by careful choice of catalyst and reaction conditions.
Medicinally relevant spirocyclic indolenines, carbazoles and quinolines can each be directly synthesised selectively from common indolyl ynone starting materials by catalyst variation (see scheme). The high yielding, divergent reactions all proceed by an initial dearomatising spirocyclisation reaction to generate an intermediate vinyl–metal species, which then rearranges selectively by careful choice of catalyst and reaction conditions.</abstract><cop>Germany</cop><pub>Blackwell Publishing Ltd</pub><pmid>27124236</pmid><doi>10.1002/chem.201601836</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Carbazoles Carbazoles - chemical synthesis Carbazoles - chemistry Catalysis Catalysts Chemical synthesis Chemistry Communication Communications diversity Indoles - chemistry Materials selection Mesylates - chemistry Metals Organic compounds Quinolines Quinolines - chemical synthesis Quinolines - chemistry Scaffolds Spiro Compounds - chemical synthesis Spiro Compounds - chemistry spirocycles Stereoisomerism Synthesis |
| title | Catalyst-Driven Scaffold Diversity: Selective Synthesis of Spirocycles, Carbazoles and Quinolines from Indolyl Ynones |
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