[Bmim]Br Accelerated One-Pot Three-Component Cascade Protocol for the Construction of Spirooxindole–Pyrrolidine Heterocyclic Hybrids
Our synthetic approach for the assembly of structurally complex spirooxindole heterocyclic hybrids was based on an ionic liquid, [bmim]Br mediated one-pot three-component cascade reaction strategy involving 1,3-dipolar cycloaddition reaction of <i>N</i>-1-(2-pyridinylmethyl)-3,5-bis[(<...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2020-10-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/25/20/4779 |
| id |
doaj-450be24505844295a183d84f186b33ac |
|---|---|
| record_format |
Article |
| spelling |
doaj-450be24505844295a183d84f186b33ac2020-11-25T03:08:01ZengMDPI AGMolecules1420-30492020-10-01254779477910.3390/molecules25204779[Bmim]Br Accelerated One-Pot Three-Component Cascade Protocol for the Construction of Spirooxindole–Pyrrolidine Heterocyclic HybridsRaju Suresh Kumar0Dhaifallah M. Al-thamili1Abdulrahman I. Almansour2Natarajan Arumugam3Necmi Dege4Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, Samsun 55139, TurkeyOur synthetic approach for the assembly of structurally complex spirooxindole heterocyclic hybrids was based on an ionic liquid, [bmim]Br mediated one-pot three-component cascade reaction strategy involving 1,3-dipolar cycloaddition reaction of <i>N</i>-1-(2-pyridinylmethyl)-3,5-bis[(<i>E</i>)-arylmethylidene]tetrahydro-4(1<i>H</i>)-pyridinones and azomethine ylide generated in situ from isatin and L-phenyl alanine, affording a series of spirooxindole–pyrrolidine heterocyclic hybrids in good-to-excellent yields. In addition to serving as the reaction medium, [bmim]Br also functioned as a catalyst in this cycloaddition reaction and hence accelerated the reaction rate affording the cycloadducts in short reaction time.https://www.mdpi.com/1420-3049/25/20/4779one-pot cascade reactions1,3-dipolar cycloadditionionic liquidselectivityspirooxindole–pyrrolidines |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Raju Suresh Kumar Dhaifallah M. Al-thamili Abdulrahman I. Almansour Natarajan Arumugam Necmi Dege |
| spellingShingle |
Raju Suresh Kumar Dhaifallah M. Al-thamili Abdulrahman I. Almansour Natarajan Arumugam Necmi Dege [Bmim]Br Accelerated One-Pot Three-Component Cascade Protocol for the Construction of Spirooxindole–Pyrrolidine Heterocyclic Hybrids Molecules one-pot cascade reactions 1,3-dipolar cycloaddition ionic liquid selectivity spirooxindole–pyrrolidines |
| author_facet |
Raju Suresh Kumar Dhaifallah M. Al-thamili Abdulrahman I. Almansour Natarajan Arumugam Necmi Dege |
| author_sort |
Raju Suresh Kumar |
| title |
[Bmim]Br Accelerated One-Pot Three-Component Cascade Protocol for the Construction of Spirooxindole–Pyrrolidine Heterocyclic Hybrids |
| title_short |
[Bmim]Br Accelerated One-Pot Three-Component Cascade Protocol for the Construction of Spirooxindole–Pyrrolidine Heterocyclic Hybrids |
| title_full |
[Bmim]Br Accelerated One-Pot Three-Component Cascade Protocol for the Construction of Spirooxindole–Pyrrolidine Heterocyclic Hybrids |
| title_fullStr |
[Bmim]Br Accelerated One-Pot Three-Component Cascade Protocol for the Construction of Spirooxindole–Pyrrolidine Heterocyclic Hybrids |
| title_full_unstemmed |
[Bmim]Br Accelerated One-Pot Three-Component Cascade Protocol for the Construction of Spirooxindole–Pyrrolidine Heterocyclic Hybrids |
| title_sort |
[bmim]br accelerated one-pot three-component cascade protocol for the construction of spirooxindole–pyrrolidine heterocyclic hybrids |
| publisher |
MDPI AG |
| series |
Molecules |
| issn |
1420-3049 |
| publishDate |
2020-10-01 |
| description |
Our synthetic approach for the assembly of structurally complex spirooxindole heterocyclic hybrids was based on an ionic liquid, [bmim]Br mediated one-pot three-component cascade reaction strategy involving 1,3-dipolar cycloaddition reaction of <i>N</i>-1-(2-pyridinylmethyl)-3,5-bis[(<i>E</i>)-arylmethylidene]tetrahydro-4(1<i>H</i>)-pyridinones and azomethine ylide generated in situ from isatin and L-phenyl alanine, affording a series of spirooxindole–pyrrolidine heterocyclic hybrids in good-to-excellent yields. In addition to serving as the reaction medium, [bmim]Br also functioned as a catalyst in this cycloaddition reaction and hence accelerated the reaction rate affording the cycloadducts in short reaction time. |
| topic |
one-pot cascade reactions 1,3-dipolar cycloaddition ionic liquid selectivity spirooxindole–pyrrolidines |
| url |
https://www.mdpi.com/1420-3049/25/20/4779 |
| work_keys_str_mv |
AT rajusureshkumar bmimbracceleratedonepotthreecomponentcascadeprotocolfortheconstructionofspirooxindolepyrrolidineheterocyclichybrids AT dhaifallahmalthamili bmimbracceleratedonepotthreecomponentcascadeprotocolfortheconstructionofspirooxindolepyrrolidineheterocyclichybrids AT abdulrahmanialmansour bmimbracceleratedonepotthreecomponentcascadeprotocolfortheconstructionofspirooxindolepyrrolidineheterocyclichybrids AT natarajanarumugam bmimbracceleratedonepotthreecomponentcascadeprotocolfortheconstructionofspirooxindolepyrrolidineheterocyclichybrids AT necmidege bmimbracceleratedonepotthreecomponentcascadeprotocolfortheconstructionofspirooxindolepyrrolidineheterocyclichybrids |
| _version_ |
1724667643122679808 |