Synthesis of Functionalized 9-Substituted Fluorene Derivatives via Boron Trifluoride Catalysed Reaction of Coplanar 9-(Phenylethynyl)-9H-fluoren-9-ols, Aryl Aminoamides and N-Bromosuccinimide
A boron trifluoride catalysed reaction of coplanar 9-(phenylethynyl)-9H-fluoren-9-ols with various 2-aminobenzamides affords a number of highly functionalized, conjugated (Z)-2-((2-(9H-fluoren-9-ylidene)-1-phenylethylidene)amino) benzamides in excellent yield. The reaction in the presence of N-brom...
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
| Published: |
Georg Thieme Verlag KG
2021-01-01
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| Series: | SynOpen |
| Subjects: | |
| Online Access: | http://www.thieme-connect.de/DOI/DOI?10.1055/s-0040-1706015 |
| _version_ | 1818666649979453440 |
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| author | Mohanakumaran Athira Ponnusamy Shanmugam |
| author_facet | Mohanakumaran Athira Ponnusamy Shanmugam |
| author_sort | Mohanakumaran Athira |
| collection | DOAJ |
| description | A boron trifluoride catalysed reaction of coplanar 9-(phenylethynyl)-9H-fluoren-9-ols with various 2-aminobenzamides affords a number of highly functionalized, conjugated (Z)-2-((2-(9H-fluoren-9-ylidene)-1-phenylethylidene)amino) benzamides in excellent yield. The reaction in the presence of N-bromosuccinimide affords (E)-5-bromo-2-((2-bromo-2-(9H-fluoren-9-ylidene)-1-phenylethylidene)amino)benzamides in very good yields. The scope of the reaction is demonstrated by selecting N-aryl substituted 2-aminobenzamides and aminosulfonamides as reaction partners. The structures of representative compounds were established by single-crystal XRD analysis. Based on the structure of the products, a plausible mechanism via formation of allene carbocation intermediates is proposed. |
| first_indexed | 2024-12-17T06:07:54Z |
| format | Article |
| id | doaj.art-c2abf463dd5d466a95526968d7f2cb32 |
| institution | Directory Open Access Journal |
| issn | 2509-9396 |
| language | English |
| last_indexed | 2024-12-17T06:07:54Z |
| publishDate | 2021-01-01 |
| publisher | Georg Thieme Verlag KG |
| record_format | Article |
| series | SynOpen |
| spelling | doaj.art-c2abf463dd5d466a95526968d7f2cb322022-12-21T22:00:42ZengGeorg Thieme Verlag KGSynOpen2509-93962021-01-010501172410.1055/s-0040-1706015Synthesis of Functionalized 9-Substituted Fluorene Derivatives via Boron Trifluoride Catalysed Reaction of Coplanar 9-(Phenylethynyl)-9H-fluoren-9-ols, Aryl Aminoamides and N-BromosuccinimideMohanakumaran AthiraPonnusamy ShanmugamA boron trifluoride catalysed reaction of coplanar 9-(phenylethynyl)-9H-fluoren-9-ols with various 2-aminobenzamides affords a number of highly functionalized, conjugated (Z)-2-((2-(9H-fluoren-9-ylidene)-1-phenylethylidene)amino) benzamides in excellent yield. The reaction in the presence of N-bromosuccinimide affords (E)-5-bromo-2-((2-bromo-2-(9H-fluoren-9-ylidene)-1-phenylethylidene)amino)benzamides in very good yields. The scope of the reaction is demonstrated by selecting N-aryl substituted 2-aminobenzamides and aminosulfonamides as reaction partners. The structures of representative compounds were established by single-crystal XRD analysis. Based on the structure of the products, a plausible mechanism via formation of allene carbocation intermediates is proposed.http://www.thieme-connect.de/DOI/DOI?10.1055/s-0040-1706015aryl aminoamidespropargylic alcoholn-bromosuccinimidebf3·oet2 fluoreneallene |
| spellingShingle | Mohanakumaran Athira Ponnusamy Shanmugam Synthesis of Functionalized 9-Substituted Fluorene Derivatives via Boron Trifluoride Catalysed Reaction of Coplanar 9-(Phenylethynyl)-9H-fluoren-9-ols, Aryl Aminoamides and N-Bromosuccinimide SynOpen aryl aminoamides propargylic alcohol n-bromosuccinimide bf3·oet2 fluorene allene |
| title | Synthesis of Functionalized 9-Substituted Fluorene Derivatives via Boron Trifluoride Catalysed Reaction of Coplanar 9-(Phenylethynyl)-9H-fluoren-9-ols, Aryl Aminoamides and N-Bromosuccinimide |
| title_full | Synthesis of Functionalized 9-Substituted Fluorene Derivatives via Boron Trifluoride Catalysed Reaction of Coplanar 9-(Phenylethynyl)-9H-fluoren-9-ols, Aryl Aminoamides and N-Bromosuccinimide |
| title_fullStr | Synthesis of Functionalized 9-Substituted Fluorene Derivatives via Boron Trifluoride Catalysed Reaction of Coplanar 9-(Phenylethynyl)-9H-fluoren-9-ols, Aryl Aminoamides and N-Bromosuccinimide |
| title_full_unstemmed | Synthesis of Functionalized 9-Substituted Fluorene Derivatives via Boron Trifluoride Catalysed Reaction of Coplanar 9-(Phenylethynyl)-9H-fluoren-9-ols, Aryl Aminoamides and N-Bromosuccinimide |
| title_short | Synthesis of Functionalized 9-Substituted Fluorene Derivatives via Boron Trifluoride Catalysed Reaction of Coplanar 9-(Phenylethynyl)-9H-fluoren-9-ols, Aryl Aminoamides and N-Bromosuccinimide |
| title_sort | synthesis of functionalized 9 substituted fluorene derivatives via boron trifluoride catalysed reaction of coplanar 9 phenylethynyl 9h fluoren 9 ols aryl aminoamides and n bromosuccinimide |
| topic | aryl aminoamides propargylic alcohol n-bromosuccinimide bf3·oet2 fluorene allene |
| url | http://www.thieme-connect.de/DOI/DOI?10.1055/s-0040-1706015 |
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