A general synthesis of diversely substituted indazoles and hetero-aromatic derivatives from o-halo-(het)arylaldehydes or -phenones
A set of variously substituted indazoles and hetero-aromatic derivatives were synthesized from o-halo-(het)arylaldehydes using a palladium catalyzed amination followed by cyclization. Starting from phenones, this process was extended to give 3-substituted indazoles. Moreover, N-1-substituted-indazol...
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| Veröffentlicht in: | Tetrahedron 2014-11, Vol.70 (44), p.8413-8418 |
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| container_issue | 44 |
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| container_title | Tetrahedron |
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| creator | Dubost, Emmanuelle Stiebing, Silvia Ferrary, Thibault Cailly, Thomas Fabis, Frédéric Collot, Valérie |
| description | A set of variously substituted indazoles and hetero-aromatic derivatives were synthesized from o-halo-(het)arylaldehydes using a palladium catalyzed amination followed by cyclization. Starting from phenones, this process was extended to give 3-substituted indazoles. Moreover, N-1-substituted-indazoles can be reached by this strategy using an optional selective N-1-alkylation step during the process. This methodology offers a general and easy route for the synthesis of regioselectively substituted indazoles.
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| doi_str_mv | 10.1016/j.tet.2014.07.092 |
| format | Article |
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[Display omitted]</description><subject>Chemical Sciences</subject><subject>Cross-coupling</subject><subject>Cyclization</subject><subject>Derivatives</subject><subject>Heterocycles</subject><subject>Indazole</subject><subject>Methodology</subject><subject>Organic chemistry</subject><subject>Palladium</subject><subject>Strategy</subject><subject>Synthesis (chemistry)</subject><subject>Tetrahedrons</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNp9kcFu2zAMhoVhA5a1fYDddGwP9khblm3sFBTrOiDALttZkC2qVuBYmaQYyI598inIsONOFMnvJ0j9jH1EKBFQftqXiVJZAYoS2hL66g3boJCiaATKt2wDIKAQUMF79iHGPQAgVvWGvW75Cy0U9MzjeUkTRRe5t9y4lUKk-czjaYjJpVMiw91i9G8_U-R6MXyiRMEXOviDTm7khoJb82vNfZuL3BeTnn1xn8EHHc6zng1NZ5PbPvDiONHiF4q37J3Vc6S7v_GG_Xz68uPxudh9__rtcbsrxlqKVFhJ0FNV900jwKLtBqtrO1S6HQfZWeigx8q03UCUE8Layh6xbsQohGioqW_Yw3VuXkodgzvklZTXTj1vd-pSy7-DiNCtmNn7K3sM_teJYlIHF0eaZ72QP0WFrRCybWrZZxSv6Bh8jIHsv9kI6uKN2qvsjbp4o6BV2Zus-XzVUL53dRRUHB0tIxkXaEzKePcf9R_mDpjt</recordid><startdate>20141104</startdate><enddate>20141104</enddate><creator>Dubost, Emmanuelle</creator><creator>Stiebing, Silvia</creator><creator>Ferrary, Thibault</creator><creator>Cailly, Thomas</creator><creator>Fabis, Frédéric</creator><creator>Collot, Valérie</creator><general>Elsevier Ltd</general><general>Elsevier</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope><scope>1XC</scope><orcidid>https://orcid.org/0000-0002-2692-7686</orcidid><orcidid>https://orcid.org/0000-0002-5262-4494</orcidid></search><sort><creationdate>20141104</creationdate><title>A general synthesis of diversely substituted indazoles and hetero-aromatic derivatives from o-halo-(het)arylaldehydes or -phenones</title><author>Dubost, Emmanuelle ; Stiebing, Silvia ; Ferrary, Thibault ; Cailly, Thomas ; Fabis, Frédéric ; Collot, Valérie</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c364t-f6e09e2395540f1f8bfa3fb2a7cb68f080912d78beef08e13f6911354c4445e53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>Chemical Sciences</topic><topic>Cross-coupling</topic><topic>Cyclization</topic><topic>Derivatives</topic><topic>Heterocycles</topic><topic>Indazole</topic><topic>Methodology</topic><topic>Organic chemistry</topic><topic>Palladium</topic><topic>Strategy</topic><topic>Synthesis (chemistry)</topic><topic>Tetrahedrons</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dubost, Emmanuelle</creatorcontrib><creatorcontrib>Stiebing, Silvia</creatorcontrib><creatorcontrib>Ferrary, Thibault</creatorcontrib><creatorcontrib>Cailly, Thomas</creatorcontrib><creatorcontrib>Fabis, Frédéric</creatorcontrib><creatorcontrib>Collot, Valérie</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>Hyper Article en Ligne (HAL)</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Dubost, Emmanuelle</au><au>Stiebing, Silvia</au><au>Ferrary, Thibault</au><au>Cailly, Thomas</au><au>Fabis, Frédéric</au><au>Collot, Valérie</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A general synthesis of diversely substituted indazoles and hetero-aromatic derivatives from o-halo-(het)arylaldehydes or -phenones</atitle><jtitle>Tetrahedron</jtitle><date>2014-11-04</date><risdate>2014</risdate><volume>70</volume><issue>44</issue><spage>8413</spage><epage>8418</epage><pages>8413-8418</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><abstract>A set of variously substituted indazoles and hetero-aromatic derivatives were synthesized from o-halo-(het)arylaldehydes using a palladium catalyzed amination followed by cyclization. Starting from phenones, this process was extended to give 3-substituted indazoles. Moreover, N-1-substituted-indazoles can be reached by this strategy using an optional selective N-1-alkylation step during the process. This methodology offers a general and easy route for the synthesis of regioselectively substituted indazoles.
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| ispartof | Tetrahedron, 2014-11, Vol.70 (44), p.8413-8418 |
| issn | 0040-4020 1464-5416 |
| language | eng |
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| source | Elsevier ScienceDirect Journals |
| subjects | Chemical Sciences Cross-coupling Cyclization Derivatives Heterocycles Indazole Methodology Organic chemistry Palladium Strategy Synthesis (chemistry) Tetrahedrons |
| title | A general synthesis of diversely substituted indazoles and hetero-aromatic derivatives from o-halo-(het)arylaldehydes or -phenones |
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