Facile access to 3-sulfonylquinolines via Knoevenagel condensation/aza-Wittig reaction cascade involving ortho-azidobenzaldehydes and β-ketosulfonamides and sulfones
Quinoline-based sulfonyl derivatives, and especially sulfonamides, are relevant and promising structures for drug design. We have developed a new convenient protocol for the synthesis of 3-sulfonyl-substituted quinolines (sulfonamides and sulfones). The approach is based on a Knoevenagel condensatio...
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2023-06-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.19.60 |
| _version_ | 1797752399356493824 |
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| author | Ksenia Malkova Andrey Bubyrev Stanislav Kalinin Dmitry Dar’in |
| author_facet | Ksenia Malkova Andrey Bubyrev Stanislav Kalinin Dmitry Dar’in |
| author_sort | Ksenia Malkova |
| collection | DOAJ |
| description | Quinoline-based sulfonyl derivatives, and especially sulfonamides, are relevant and promising structures for drug design. We have developed a new convenient protocol for the synthesis of 3-sulfonyl-substituted quinolines (sulfonamides and sulfones). The approach is based on a Knoevenagel condensation/aza-Wittig reaction cascade involving o-azidobenzaldehydes and ketosulfonamides or ketosulfones as key building blocks. The protocol is appropriate for both ketosulfonyl reagents and α-sulfonyl-substituted alkyl acetates providing the target quinoline derivatives in good to excellent yields. |
| first_indexed | 2024-03-12T17:02:47Z |
| format | Article |
| id | doaj.art-3f2caa2aad3f417ab872886a1ba98e60 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-03-12T17:02:47Z |
| publishDate | 2023-06-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-3f2caa2aad3f417ab872886a1ba98e602023-08-07T08:43:25ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972023-06-0119180080710.3762/bjoc.19.601860-5397-19-60Facile access to 3-sulfonylquinolines via Knoevenagel condensation/aza-Wittig reaction cascade involving ortho-azidobenzaldehydes and β-ketosulfonamides and sulfonesKsenia Malkova0Andrey Bubyrev1Stanislav Kalinin2Dmitry Dar’in3Saint Petersburg State University, Saint Petersburg 199034, Russian Federation Saint Petersburg State University, Saint Petersburg 199034, Russian Federation Saint Petersburg State University, Saint Petersburg 199034, Russian Federation Saint Petersburg State University, Saint Petersburg 199034, Russian Federation Quinoline-based sulfonyl derivatives, and especially sulfonamides, are relevant and promising structures for drug design. We have developed a new convenient protocol for the synthesis of 3-sulfonyl-substituted quinolines (sulfonamides and sulfones). The approach is based on a Knoevenagel condensation/aza-Wittig reaction cascade involving o-azidobenzaldehydes and ketosulfonamides or ketosulfones as key building blocks. The protocol is appropriate for both ketosulfonyl reagents and α-sulfonyl-substituted alkyl acetates providing the target quinoline derivatives in good to excellent yields.https://doi.org/10.3762/bjoc.19.60aza-wittig reactionazidescyclocondensationquinolonessulfonamides |
| spellingShingle | Ksenia Malkova Andrey Bubyrev Stanislav Kalinin Dmitry Dar’in Facile access to 3-sulfonylquinolines via Knoevenagel condensation/aza-Wittig reaction cascade involving ortho-azidobenzaldehydes and β-ketosulfonamides and sulfones Beilstein Journal of Organic Chemistry aza-wittig reaction azides cyclocondensation quinolones sulfonamides |
| title | Facile access to 3-sulfonylquinolines via Knoevenagel condensation/aza-Wittig reaction cascade involving ortho-azidobenzaldehydes and β-ketosulfonamides and sulfones |
| title_full | Facile access to 3-sulfonylquinolines via Knoevenagel condensation/aza-Wittig reaction cascade involving ortho-azidobenzaldehydes and β-ketosulfonamides and sulfones |
| title_fullStr | Facile access to 3-sulfonylquinolines via Knoevenagel condensation/aza-Wittig reaction cascade involving ortho-azidobenzaldehydes and β-ketosulfonamides and sulfones |
| title_full_unstemmed | Facile access to 3-sulfonylquinolines via Knoevenagel condensation/aza-Wittig reaction cascade involving ortho-azidobenzaldehydes and β-ketosulfonamides and sulfones |
| title_short | Facile access to 3-sulfonylquinolines via Knoevenagel condensation/aza-Wittig reaction cascade involving ortho-azidobenzaldehydes and β-ketosulfonamides and sulfones |
| title_sort | facile access to 3 sulfonylquinolines via knoevenagel condensation aza wittig reaction cascade involving ortho azidobenzaldehydes and β ketosulfonamides and sulfones |
| topic | aza-wittig reaction azides cyclocondensation quinolones sulfonamides |
| url | https://doi.org/10.3762/bjoc.19.60 |
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