Ultrasound assisted Mizoroki–Heck coupling/C–H amination in a single pot: Direct synthesis of indole derivatives
A one-pot protocol based on coupling-cyclization strategy has been developed for the construction of indole ring leading to 2-substituted indole derivatives. The methodology involved ultrasound assisted Mizoroki–Heck coupling in the initial step followed by C–H amination in the second step in the sa...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Elsevier
2019-12-01
|
| Series: | Arabian Journal of Chemistry |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S187853521630082X |
| _version_ | 1811320607757828096 |
|---|---|
| author | A.S.G. Prasad T. Bhaskara Rao D. Rambabu M.V. Basaveswara Rao Manojit Pal |
| author_facet | A.S.G. Prasad T. Bhaskara Rao D. Rambabu M.V. Basaveswara Rao Manojit Pal |
| author_sort | A.S.G. Prasad |
| collection | DOAJ |
| description | A one-pot protocol based on coupling-cyclization strategy has been developed for the construction of indole ring leading to 2-substituted indole derivatives. The methodology involved ultrasound assisted Mizoroki–Heck coupling in the initial step followed by C–H amination in the second step in the same pot. The C–C bond forming reaction in the first step was catalyzed by Pd/C-PPh3 catalyst system whereas the C–N bond formation in the second step was mediated by DDQ. A number of indoles were prepared in good to acceptable yield by treating 2-iodosulfanilides with various alkenes under this condition. The rapid conversions along with the use of inexpensive catalyst as well as oxidant are key features of this method. Keywords: Indole, Mizoroki–Heck coupling, Pd/C, C–H amination, Ultrasound |
| first_indexed | 2024-04-13T13:01:00Z |
| format | Article |
| id | doaj.art-b331cc5ded92406cb84a2d302139b5e9 |
| institution | Directory Open Access Journal |
| issn | 1878-5352 |
| language | English |
| last_indexed | 2024-04-13T13:01:00Z |
| publishDate | 2019-12-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Arabian Journal of Chemistry |
| spelling | doaj.art-b331cc5ded92406cb84a2d302139b5e92022-12-22T02:45:54ZengElsevierArabian Journal of Chemistry1878-53522019-12-0112843204330Ultrasound assisted Mizoroki–Heck coupling/C–H amination in a single pot: Direct synthesis of indole derivativesA.S.G. Prasad0T. Bhaskara Rao1D. Rambabu2M.V. Basaveswara Rao3Manojit Pal4Department of Chemistry, K. L. University, Vaddeswaram, Guntur 522502, Andhra Pradesh, IndiaDepartment of Chemistry, K. L. University, Vaddeswaram, Guntur 522502, Andhra Pradesh, IndiaDepartment of Chemistry and the National Institute for Biotechnology in the Negev, Ben-Gurion University of the Negev, Be’er-Sheva 84105, IsraelDepartment of Chemistry, Krishna University, Krishna District, Andhra Pradesh, India; Corresponding authors.Dr. Reddy’s Institute of Life Sciences, University of Hyderabad Campus, Hyderabad 500046, India; Corresponding authors.A one-pot protocol based on coupling-cyclization strategy has been developed for the construction of indole ring leading to 2-substituted indole derivatives. The methodology involved ultrasound assisted Mizoroki–Heck coupling in the initial step followed by C–H amination in the second step in the same pot. The C–C bond forming reaction in the first step was catalyzed by Pd/C-PPh3 catalyst system whereas the C–N bond formation in the second step was mediated by DDQ. A number of indoles were prepared in good to acceptable yield by treating 2-iodosulfanilides with various alkenes under this condition. The rapid conversions along with the use of inexpensive catalyst as well as oxidant are key features of this method. Keywords: Indole, Mizoroki–Heck coupling, Pd/C, C–H amination, Ultrasoundhttp://www.sciencedirect.com/science/article/pii/S187853521630082X |
| spellingShingle | A.S.G. Prasad T. Bhaskara Rao D. Rambabu M.V. Basaveswara Rao Manojit Pal Ultrasound assisted Mizoroki–Heck coupling/C–H amination in a single pot: Direct synthesis of indole derivatives Arabian Journal of Chemistry |
| title | Ultrasound assisted Mizoroki–Heck coupling/C–H amination in a single pot: Direct synthesis of indole derivatives |
| title_full | Ultrasound assisted Mizoroki–Heck coupling/C–H amination in a single pot: Direct synthesis of indole derivatives |
| title_fullStr | Ultrasound assisted Mizoroki–Heck coupling/C–H amination in a single pot: Direct synthesis of indole derivatives |
| title_full_unstemmed | Ultrasound assisted Mizoroki–Heck coupling/C–H amination in a single pot: Direct synthesis of indole derivatives |
| title_short | Ultrasound assisted Mizoroki–Heck coupling/C–H amination in a single pot: Direct synthesis of indole derivatives |
| title_sort | ultrasound assisted mizoroki heck coupling c h amination in a single pot direct synthesis of indole derivatives |
| url | http://www.sciencedirect.com/science/article/pii/S187853521630082X |
| work_keys_str_mv | AT asgprasad ultrasoundassistedmizorokiheckcouplingchaminationinasinglepotdirectsynthesisofindolederivatives AT tbhaskararao ultrasoundassistedmizorokiheckcouplingchaminationinasinglepotdirectsynthesisofindolederivatives AT drambabu ultrasoundassistedmizorokiheckcouplingchaminationinasinglepotdirectsynthesisofindolederivatives AT mvbasaveswararao ultrasoundassistedmizorokiheckcouplingchaminationinasinglepotdirectsynthesisofindolederivatives AT manojitpal ultrasoundassistedmizorokiheckcouplingchaminationinasinglepotdirectsynthesisofindolederivatives |