Green Organoselenium Chemistry: Selective Syntheses of New 1,4-Thiaselenine Derivatives Based on Reactions of Thiaselenole Reagent with Alcohols and Water
Environmentally friendly synthetic methods were developed for the selective preparation of new 2,3-dihydro-1,4-thiaselenine derivatives in high yields based on the reactions of 2-bromomethyl-1,3-thiaselenole with alcohols and water at room temperature. The reaction of 2-bromomethyl-1,3-thiaselenole...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2023-06-01
|
| Series: | Inorganics |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2304-6740/11/7/281 |
| _version_ | 1827732874659364864 |
|---|---|
| author | Svetlana V. Amosova Andrey S. Filippov Nataliya A. Makhaeva Alexander I. Albanov Vladimir A. Potapov |
| author_facet | Svetlana V. Amosova Andrey S. Filippov Nataliya A. Makhaeva Alexander I. Albanov Vladimir A. Potapov |
| author_sort | Svetlana V. Amosova |
| collection | DOAJ |
| description | Environmentally friendly synthetic methods were developed for the selective preparation of new 2,3-dihydro-1,4-thiaselenine derivatives in high yields based on the reactions of 2-bromomethyl-1,3-thiaselenole with alcohols and water at room temperature. The reaction of 2-bromomethyl-1,3-thiaselenole with alcohols was accompanied by a rearrangement with ring extension, leading to six-membered heterocyclic compounds, a new family of 2-organyloxy-2,3-dihydro-1,4-thiaselenines, in 80–96% yields. The remarkable cascade reactions of 2-bromomethyl-1,3-thiaselenole with water afforded 2,3-dihydro-1,4-thiaselenines functionalized with the (<i>Z</i>)-S-CH=CH-Se fragment and one or two highly reactive aldehyde groups. The latter aldehydes were functionalized by the reactions with alcohols and glycols to give new polyfunctionalized compounds, containing two double bonds, two sulfur atoms, two selenium atoms, and two or four oxygen atoms, in high yields. |
| first_indexed | 2024-03-11T00:59:09Z |
| format | Article |
| id | doaj.art-debca56c13854a9185dc4b4d1d43c692 |
| institution | Directory Open Access Journal |
| issn | 2304-6740 |
| language | English |
| last_indexed | 2024-03-11T00:59:09Z |
| publishDate | 2023-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Inorganics |
| spelling | doaj.art-debca56c13854a9185dc4b4d1d43c6922023-11-18T19:47:52ZengMDPI AGInorganics2304-67402023-06-0111728110.3390/inorganics11070281Green Organoselenium Chemistry: Selective Syntheses of New 1,4-Thiaselenine Derivatives Based on Reactions of Thiaselenole Reagent with Alcohols and WaterSvetlana V. Amosova0Andrey S. Filippov1Nataliya A. Makhaeva2Alexander I. Albanov3Vladimir A. Potapov4A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of The Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, RussiaA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of The Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, RussiaA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of The Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, RussiaA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of The Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, RussiaA. E. Favorsky Irkutsk Institute of Chemistry, Siberian Division of The Russian Academy of Sciences, 1 Favorsky Str., Irkutsk 664033, RussiaEnvironmentally friendly synthetic methods were developed for the selective preparation of new 2,3-dihydro-1,4-thiaselenine derivatives in high yields based on the reactions of 2-bromomethyl-1,3-thiaselenole with alcohols and water at room temperature. The reaction of 2-bromomethyl-1,3-thiaselenole with alcohols was accompanied by a rearrangement with ring extension, leading to six-membered heterocyclic compounds, a new family of 2-organyloxy-2,3-dihydro-1,4-thiaselenines, in 80–96% yields. The remarkable cascade reactions of 2-bromomethyl-1,3-thiaselenole with water afforded 2,3-dihydro-1,4-thiaselenines functionalized with the (<i>Z</i>)-S-CH=CH-Se fragment and one or two highly reactive aldehyde groups. The latter aldehydes were functionalized by the reactions with alcohols and glycols to give new polyfunctionalized compounds, containing two double bonds, two sulfur atoms, two selenium atoms, and two or four oxygen atoms, in high yields.https://www.mdpi.com/2304-6740/11/7/281alcohols2-bromomethyl-1,3-thiaselenoledihydro-1,4-thiaselenine derivativesheterocyclic compoundsnucleophilic reactionswater |
| spellingShingle | Svetlana V. Amosova Andrey S. Filippov Nataliya A. Makhaeva Alexander I. Albanov Vladimir A. Potapov Green Organoselenium Chemistry: Selective Syntheses of New 1,4-Thiaselenine Derivatives Based on Reactions of Thiaselenole Reagent with Alcohols and Water Inorganics alcohols 2-bromomethyl-1,3-thiaselenole dihydro-1,4-thiaselenine derivatives heterocyclic compounds nucleophilic reactions water |
| title | Green Organoselenium Chemistry: Selective Syntheses of New 1,4-Thiaselenine Derivatives Based on Reactions of Thiaselenole Reagent with Alcohols and Water |
| title_full | Green Organoselenium Chemistry: Selective Syntheses of New 1,4-Thiaselenine Derivatives Based on Reactions of Thiaselenole Reagent with Alcohols and Water |
| title_fullStr | Green Organoselenium Chemistry: Selective Syntheses of New 1,4-Thiaselenine Derivatives Based on Reactions of Thiaselenole Reagent with Alcohols and Water |
| title_full_unstemmed | Green Organoselenium Chemistry: Selective Syntheses of New 1,4-Thiaselenine Derivatives Based on Reactions of Thiaselenole Reagent with Alcohols and Water |
| title_short | Green Organoselenium Chemistry: Selective Syntheses of New 1,4-Thiaselenine Derivatives Based on Reactions of Thiaselenole Reagent with Alcohols and Water |
| title_sort | green organoselenium chemistry selective syntheses of new 1 4 thiaselenine derivatives based on reactions of thiaselenole reagent with alcohols and water |
| topic | alcohols 2-bromomethyl-1,3-thiaselenole dihydro-1,4-thiaselenine derivatives heterocyclic compounds nucleophilic reactions water |
| url | https://www.mdpi.com/2304-6740/11/7/281 |
| work_keys_str_mv | AT svetlanavamosova greenorganoseleniumchemistryselectivesynthesesofnew14thiaseleninederivativesbasedonreactionsofthiaselenolereagentwithalcoholsandwater AT andreysfilippov greenorganoseleniumchemistryselectivesynthesesofnew14thiaseleninederivativesbasedonreactionsofthiaselenolereagentwithalcoholsandwater AT nataliyaamakhaeva greenorganoseleniumchemistryselectivesynthesesofnew14thiaseleninederivativesbasedonreactionsofthiaselenolereagentwithalcoholsandwater AT alexanderialbanov greenorganoseleniumchemistryselectivesynthesesofnew14thiaseleninederivativesbasedonreactionsofthiaselenolereagentwithalcoholsandwater AT vladimirapotapov greenorganoseleniumchemistryselectivesynthesesofnew14thiaseleninederivativesbasedonreactionsofthiaselenolereagentwithalcoholsandwater |