Anthracene-fused isoxazolopyrrolo[2,1-a]isoquinolines via an endocyclic N-acyliminium ion cyclization: a joint experimental and theoretical study
A simple and efficient strategy is reported for the synthesis of anthracene-fused isoxazolopyrrolo[2,1-a]isoquinolines via an endocyclic N-acyliminium ion cyclization. The cyclization of 18-aryl-21-(2-arylethyl)-22-hydroxy-16-oxa-17,21-diazahexacyclo[6.6.5.315,19.02,7.09,14.015,19]docosa-2,4,6,9,11,...
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| Veröffentlicht in: | Tetrahedron 2016-08, Vol.72 (32), p.4827-4834 |
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| creator | Ledovskaya, Maria S. Molchanov, Alexander P. Kostikov, Rafael R. Panikorovsky, Taras L. Gurzhiy, Vladislav V. Ryazantsev, Mikhail N. Boitsov, Vitali M. Stepakov, Alexander V. |
| description | A simple and efficient strategy is reported for the synthesis of anthracene-fused isoxazolopyrrolo[2,1-a]isoquinolines via an endocyclic N-acyliminium ion cyclization. The cyclization of 18-aryl-21-(2-arylethyl)-22-hydroxy-16-oxa-17,21-diazahexacyclo[6.6.5.315,19.02,7.09,14.015,19]docosa-2,4,6,9,11,13,17-heptaen-20-ones proceeds with high stereoselectivity, leading to 28-aryl-30-oxa-12,29-diazaoctacyclo[13.6.6.32,14.02,14.03,12.04,9.016,21.022,27]triaconta-4,6,8,16,18,20,22,24,26,28-decaen-13-ones. The N-acyliminium cyclization of 18-aryl-21-(2-arylethyl)-20-hydroxy-16-oxa-17,21-diazahexacyclo[6.6.5.315,19.02,7.09,14.015,19]docosa-2,4,6,9,11,13,17-heptaen-22-ones occurs only for substrates with electron-rich aromatic groups in the arylalkyl fragment. In these cases, cyclization also proceeds with a high stereoselectivity with the formation of anthracene-fused isoxazolopyrrolo[2,1-a]isoquinolines as single diastereomers. To understand the mechanisms that allow for cyclization of N-acyliminium ion a quantum chemical investigation was performed.
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| doi_str_mv | 10.1016/j.tet.2016.06.048 |
| format | Article |
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[Display omitted]</description><subject>Dihydroisoxazoles</subject><subject>Formations</subject><subject>Fragmentation</subject><subject>Hydroxylactams</subject><subject>Intramolecular cyclization</subject><subject>N-Acyliminium ion</subject><subject>Quantum chemical investigation</subject><subject>Quantum chemistry</subject><subject>Stereoselectivity</subject><subject>Strategy</subject><subject>Substrates</subject><subject>Synthesis (chemistry)</subject><subject>Tetrahedrons</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNp9UMtu1DAUtRBIDIUPYOclCzK1HcdJYFVVPCpV7aZdIWT5caPeUcYebKdq-hf8MR6GNdKVzn2dI51DyHvOtpxxdb7bFihbUdstqyWHF2TDpZJNJ7l6STaMSdZIJthr8ibnHWOMc9FuyO-LUB6ScRCgmZYMnmKOT-Y5zvGwplThh_jIG_Ozrn8tGOKMATJ9RENNoBB8dKub0dGbxrh1xj0GXPYUY6B_D8-m1P4TNXQXMRQKTwdIuIdQzFwVPC0PEBMUdHXOZfHrW_JqMnOGd__wjNx__XJ3-b25vv12dXlx3bi2ZaXp3cSVkMMoBTPMyM4K7-yoBFfdYJj1U2-tl75TAHayrZ-EH0clbc8tiF62Z-TDSfeQqjPIRe8xO5hnEyAuWfOh7ZRUYz_UV356dSnmnGDSh-rBpFVzpo_x652u8etj_JrVkkfO5xMHqodHhKSzQwgOPCZwRfuI_2H_AX2PkiY</recordid><startdate>20160811</startdate><enddate>20160811</enddate><creator>Ledovskaya, Maria S.</creator><creator>Molchanov, Alexander P.</creator><creator>Kostikov, Rafael R.</creator><creator>Panikorovsky, Taras L.</creator><creator>Gurzhiy, Vladislav V.</creator><creator>Ryazantsev, Mikhail N.</creator><creator>Boitsov, Vitali M.</creator><creator>Stepakov, Alexander V.</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>20160811</creationdate><title>Anthracene-fused isoxazolopyrrolo[2,1-a]isoquinolines via an endocyclic N-acyliminium ion cyclization: a joint experimental and theoretical study</title><author>Ledovskaya, Maria S. ; Molchanov, Alexander P. ; Kostikov, Rafael R. ; Panikorovsky, Taras L. ; Gurzhiy, Vladislav V. ; Ryazantsev, Mikhail N. ; Boitsov, Vitali M. ; Stepakov, Alexander V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c330t-7cf162489420a0a45b2dcb9621658a0bdf7bbd4d56eebfb3df2d9964b71be2743</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Dihydroisoxazoles</topic><topic>Formations</topic><topic>Fragmentation</topic><topic>Hydroxylactams</topic><topic>Intramolecular cyclization</topic><topic>N-Acyliminium ion</topic><topic>Quantum chemical investigation</topic><topic>Quantum chemistry</topic><topic>Stereoselectivity</topic><topic>Strategy</topic><topic>Substrates</topic><topic>Synthesis (chemistry)</topic><topic>Tetrahedrons</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ledovskaya, Maria S.</creatorcontrib><creatorcontrib>Molchanov, Alexander P.</creatorcontrib><creatorcontrib>Kostikov, Rafael R.</creatorcontrib><creatorcontrib>Panikorovsky, Taras L.</creatorcontrib><creatorcontrib>Gurzhiy, Vladislav V.</creatorcontrib><creatorcontrib>Ryazantsev, Mikhail N.</creatorcontrib><creatorcontrib>Boitsov, Vitali M.</creatorcontrib><creatorcontrib>Stepakov, Alexander V.</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ledovskaya, Maria S.</au><au>Molchanov, Alexander P.</au><au>Kostikov, Rafael R.</au><au>Panikorovsky, Taras L.</au><au>Gurzhiy, Vladislav V.</au><au>Ryazantsev, Mikhail N.</au><au>Boitsov, Vitali M.</au><au>Stepakov, Alexander V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Anthracene-fused isoxazolopyrrolo[2,1-a]isoquinolines via an endocyclic N-acyliminium ion cyclization: a joint experimental and theoretical study</atitle><jtitle>Tetrahedron</jtitle><date>2016-08-11</date><risdate>2016</risdate><volume>72</volume><issue>32</issue><spage>4827</spage><epage>4834</epage><pages>4827-4834</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><abstract>A simple and efficient strategy is reported for the synthesis of anthracene-fused isoxazolopyrrolo[2,1-a]isoquinolines via an endocyclic N-acyliminium ion cyclization. The cyclization of 18-aryl-21-(2-arylethyl)-22-hydroxy-16-oxa-17,21-diazahexacyclo[6.6.5.315,19.02,7.09,14.015,19]docosa-2,4,6,9,11,13,17-heptaen-20-ones proceeds with high stereoselectivity, leading to 28-aryl-30-oxa-12,29-diazaoctacyclo[13.6.6.32,14.02,14.03,12.04,9.016,21.022,27]triaconta-4,6,8,16,18,20,22,24,26,28-decaen-13-ones. The N-acyliminium cyclization of 18-aryl-21-(2-arylethyl)-20-hydroxy-16-oxa-17,21-diazahexacyclo[6.6.5.315,19.02,7.09,14.015,19]docosa-2,4,6,9,11,13,17-heptaen-22-ones occurs only for substrates with electron-rich aromatic groups in the arylalkyl fragment. In these cases, cyclization also proceeds with a high stereoselectivity with the formation of anthracene-fused isoxazolopyrrolo[2,1-a]isoquinolines as single diastereomers. To understand the mechanisms that allow for cyclization of N-acyliminium ion a quantum chemical investigation was performed.
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| subjects | Dihydroisoxazoles Formations Fragmentation Hydroxylactams Intramolecular cyclization N-Acyliminium ion Quantum chemical investigation Quantum chemistry Stereoselectivity Strategy Substrates Synthesis (chemistry) Tetrahedrons |
| title | Anthracene-fused isoxazolopyrrolo[2,1-a]isoquinolines via an endocyclic N-acyliminium ion cyclization: a joint experimental and theoretical study |
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