Efficient Synthesis of 3-Sulfonyl-2-sulfonylmethyl-2<i>H</i>-chromenes via Tandem Knoevenagel Condensation/Oxa-Michael Addition Protocol
An organocatalytic [4 + 2] cascade annulation of salicylaldehydes and 1,3-bisarylsulfonylpropenes has been developed. This protocol enables the efficient and straightforward synthesis of a new series of 3-sulfonyl-2-sulfonylmethyl-2<i>H</i>-chromenes that are useful for exploring pharmac...
| Main Authors: | , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2022-04-01
|
| Series: | Catalysts |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2073-4344/12/5/491 |
| _version_ | 1797501006370570240 |
|---|---|
| author | Lin Jiang Peiying Peng Min Li Lu Li Menglin Zhao Minglong Yuan Mingwei Yuan |
| author_facet | Lin Jiang Peiying Peng Min Li Lu Li Menglin Zhao Minglong Yuan Mingwei Yuan |
| author_sort | Lin Jiang |
| collection | DOAJ |
| description | An organocatalytic [4 + 2] cascade annulation of salicylaldehydes and 1,3-bisarylsulfonylpropenes has been developed. This protocol enables the efficient and straightforward synthesis of a new series of 3-sulfonyl-2-sulfonylmethyl-2<i>H</i>-chromenes that are useful for exploring pharmacologically valued compounds. Further reductive modifications result in 3-desulfonylated chromene or chromane derivatives. This protocol can be expanded to the synthesis of 3-sulfonyl-2-sulfonylmethyl 1,2-dihydroquinoline. |
| first_indexed | 2024-03-10T03:12:03Z |
| format | Article |
| id | doaj.art-e287ed84b97e42acb235a6d6b648ae95 |
| institution | Directory Open Access Journal |
| issn | 2073-4344 |
| language | English |
| last_indexed | 2024-03-10T03:12:03Z |
| publishDate | 2022-04-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Catalysts |
| spelling | doaj.art-e287ed84b97e42acb235a6d6b648ae952023-11-23T10:25:40ZengMDPI AGCatalysts2073-43442022-04-0112549110.3390/catal12050491Efficient Synthesis of 3-Sulfonyl-2-sulfonylmethyl-2<i>H</i>-chromenes via Tandem Knoevenagel Condensation/Oxa-Michael Addition ProtocolLin Jiang0Peiying Peng1Min Li2Lu Li3Menglin Zhao4Minglong Yuan5Mingwei Yuan6National and Local Joint Engineering Research Center for Green Preparation Technology of Biobased Materials, School of Chemistry and Environment, Yunnan Minzu University, Kunming 650504, ChinaNational and Local Joint Engineering Research Center for Green Preparation Technology of Biobased Materials, School of Chemistry and Environment, Yunnan Minzu University, Kunming 650504, ChinaNational and Local Joint Engineering Research Center for Green Preparation Technology of Biobased Materials, School of Chemistry and Environment, Yunnan Minzu University, Kunming 650504, ChinaNational and Local Joint Engineering Research Center for Green Preparation Technology of Biobased Materials, School of Chemistry and Environment, Yunnan Minzu University, Kunming 650504, ChinaNational and Local Joint Engineering Research Center for Green Preparation Technology of Biobased Materials, School of Chemistry and Environment, Yunnan Minzu University, Kunming 650504, ChinaNational and Local Joint Engineering Research Center for Green Preparation Technology of Biobased Materials, School of Chemistry and Environment, Yunnan Minzu University, Kunming 650504, ChinaNational and Local Joint Engineering Research Center for Green Preparation Technology of Biobased Materials, School of Chemistry and Environment, Yunnan Minzu University, Kunming 650504, ChinaAn organocatalytic [4 + 2] cascade annulation of salicylaldehydes and 1,3-bisarylsulfonylpropenes has been developed. This protocol enables the efficient and straightforward synthesis of a new series of 3-sulfonyl-2-sulfonylmethyl-2<i>H</i>-chromenes that are useful for exploring pharmacologically valued compounds. Further reductive modifications result in 3-desulfonylated chromene or chromane derivatives. This protocol can be expanded to the synthesis of 3-sulfonyl-2-sulfonylmethyl 1,2-dihydroquinoline.https://www.mdpi.com/2073-4344/12/5/4912<i>H</i>-chromene[4 + 2] annulationsalicylaldehyde1,3-bisarylsulfonylpropeneorganocatalysis |
| spellingShingle | Lin Jiang Peiying Peng Min Li Lu Li Menglin Zhao Minglong Yuan Mingwei Yuan Efficient Synthesis of 3-Sulfonyl-2-sulfonylmethyl-2<i>H</i>-chromenes via Tandem Knoevenagel Condensation/Oxa-Michael Addition Protocol Catalysts 2<i>H</i>-chromene [4 + 2] annulation salicylaldehyde 1,3-bisarylsulfonylpropene organocatalysis |
| title | Efficient Synthesis of 3-Sulfonyl-2-sulfonylmethyl-2<i>H</i>-chromenes via Tandem Knoevenagel Condensation/Oxa-Michael Addition Protocol |
| title_full | Efficient Synthesis of 3-Sulfonyl-2-sulfonylmethyl-2<i>H</i>-chromenes via Tandem Knoevenagel Condensation/Oxa-Michael Addition Protocol |
| title_fullStr | Efficient Synthesis of 3-Sulfonyl-2-sulfonylmethyl-2<i>H</i>-chromenes via Tandem Knoevenagel Condensation/Oxa-Michael Addition Protocol |
| title_full_unstemmed | Efficient Synthesis of 3-Sulfonyl-2-sulfonylmethyl-2<i>H</i>-chromenes via Tandem Knoevenagel Condensation/Oxa-Michael Addition Protocol |
| title_short | Efficient Synthesis of 3-Sulfonyl-2-sulfonylmethyl-2<i>H</i>-chromenes via Tandem Knoevenagel Condensation/Oxa-Michael Addition Protocol |
| title_sort | efficient synthesis of 3 sulfonyl 2 sulfonylmethyl 2 i h i chromenes via tandem knoevenagel condensation oxa michael addition protocol |
| topic | 2<i>H</i>-chromene [4 + 2] annulation salicylaldehyde 1,3-bisarylsulfonylpropene organocatalysis |
| url | https://www.mdpi.com/2073-4344/12/5/491 |
| work_keys_str_mv | AT linjiang efficientsynthesisof3sulfonyl2sulfonylmethyl2ihichromenesviatandemknoevenagelcondensationoxamichaeladditionprotocol AT peiyingpeng efficientsynthesisof3sulfonyl2sulfonylmethyl2ihichromenesviatandemknoevenagelcondensationoxamichaeladditionprotocol AT minli efficientsynthesisof3sulfonyl2sulfonylmethyl2ihichromenesviatandemknoevenagelcondensationoxamichaeladditionprotocol AT luli efficientsynthesisof3sulfonyl2sulfonylmethyl2ihichromenesviatandemknoevenagelcondensationoxamichaeladditionprotocol AT menglinzhao efficientsynthesisof3sulfonyl2sulfonylmethyl2ihichromenesviatandemknoevenagelcondensationoxamichaeladditionprotocol AT minglongyuan efficientsynthesisof3sulfonyl2sulfonylmethyl2ihichromenesviatandemknoevenagelcondensationoxamichaeladditionprotocol AT mingweiyuan efficientsynthesisof3sulfonyl2sulfonylmethyl2ihichromenesviatandemknoevenagelcondensationoxamichaeladditionprotocol |