An oxidative amidation and heterocyclization approach for the synthesis of β-carbolines and dihydroeudistomin Y
A novel synthetic methodology has been developed for the synthesis of dihydro-β-carboline derivatives employing oxidative amidation–Bischler–Napieralski reaction conditions using tryptamine and 2,2-dibromo-1-phenylethanone as key starting materials. A number of dihydro-β-carboline derivatives have b...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Beilstein-Institut
2014-02-01
|
| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.10.45 |
| _version_ | 1818932868536074240 |
|---|---|
| author | Suresh Babu Meruva Akula Raghunadh Raghavendra Rao Kamaraju U. K. Syam Kumar P. K. Dubey |
| author_facet | Suresh Babu Meruva Akula Raghunadh Raghavendra Rao Kamaraju U. K. Syam Kumar P. K. Dubey |
| author_sort | Suresh Babu Meruva |
| collection | DOAJ |
| description | A novel synthetic methodology has been developed for the synthesis of dihydro-β-carboline derivatives employing oxidative amidation–Bischler–Napieralski reaction conditions using tryptamine and 2,2-dibromo-1-phenylethanone as key starting materials. A number of dihydro-β-carboline derivatives have been synthesized in moderate to good yields using this methodology. Attempts were made towards the conversion of these dihydro-β-carbolines to naturally occurring eudistomin alkaloids. |
| first_indexed | 2024-12-20T04:39:19Z |
| format | Article |
| id | doaj.art-403c0108898e4911b9a236a6e4a16671 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-20T04:39:19Z |
| publishDate | 2014-02-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-403c0108898e4911b9a236a6e4a166712022-12-21T19:53:10ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972014-02-0110147148010.3762/bjoc.10.451860-5397-10-45An oxidative amidation and heterocyclization approach for the synthesis of β-carbolines and dihydroeudistomin YSuresh Babu Meruva0Akula Raghunadh1Raghavendra Rao Kamaraju2U. K. Syam Kumar3P. K. Dubey4Technology Development Centre, Custom Pharmaceutical Services, Dr. Reddy’s Laboratories Ltd., Miyapur, Hyderabad – 500049, IndiaTechnology Development Centre, Custom Pharmaceutical Services, Dr. Reddy’s Laboratories Ltd., Miyapur, Hyderabad – 500049, IndiaTechnology Development Centre, Custom Pharmaceutical Services, Dr. Reddy’s Laboratories Ltd., Miyapur, Hyderabad – 500049, IndiaTechnology Development Centre, Custom Pharmaceutical Services, Dr. Reddy’s Laboratories Ltd., Miyapur, Hyderabad – 500049, IndiaDepartment of Chemistry, College of Engineering, JNTUH, Kukatpally, Hyderabad – 500085, IndiaA novel synthetic methodology has been developed for the synthesis of dihydro-β-carboline derivatives employing oxidative amidation–Bischler–Napieralski reaction conditions using tryptamine and 2,2-dibromo-1-phenylethanone as key starting materials. A number of dihydro-β-carboline derivatives have been synthesized in moderate to good yields using this methodology. Attempts were made towards the conversion of these dihydro-β-carbolines to naturally occurring eudistomin alkaloids.https://doi.org/10.3762/bjoc.10.45Bischler–Napieralski reactiondihydro-β-carboline derivativesdihydro-eudistomineudistominketo amideoxidative amidation |
| spellingShingle | Suresh Babu Meruva Akula Raghunadh Raghavendra Rao Kamaraju U. K. Syam Kumar P. K. Dubey An oxidative amidation and heterocyclization approach for the synthesis of β-carbolines and dihydroeudistomin Y Beilstein Journal of Organic Chemistry Bischler–Napieralski reaction dihydro-β-carboline derivatives dihydro-eudistomin eudistomin keto amide oxidative amidation |
| title | An oxidative amidation and heterocyclization approach for the synthesis of β-carbolines and dihydroeudistomin Y |
| title_full | An oxidative amidation and heterocyclization approach for the synthesis of β-carbolines and dihydroeudistomin Y |
| title_fullStr | An oxidative amidation and heterocyclization approach for the synthesis of β-carbolines and dihydroeudistomin Y |
| title_full_unstemmed | An oxidative amidation and heterocyclization approach for the synthesis of β-carbolines and dihydroeudistomin Y |
| title_short | An oxidative amidation and heterocyclization approach for the synthesis of β-carbolines and dihydroeudistomin Y |
| title_sort | oxidative amidation and heterocyclization approach for the synthesis of β carbolines and dihydroeudistomin y |
| topic | Bischler–Napieralski reaction dihydro-β-carboline derivatives dihydro-eudistomin eudistomin keto amide oxidative amidation |
| url | https://doi.org/10.3762/bjoc.10.45 |
| work_keys_str_mv | AT sureshbabumeruva anoxidativeamidationandheterocyclizationapproachforthesynthesisofbcarbolinesanddihydroeudistominy AT akularaghunadh anoxidativeamidationandheterocyclizationapproachforthesynthesisofbcarbolinesanddihydroeudistominy AT raghavendraraokamaraju anoxidativeamidationandheterocyclizationapproachforthesynthesisofbcarbolinesanddihydroeudistominy AT uksyamkumar anoxidativeamidationandheterocyclizationapproachforthesynthesisofbcarbolinesanddihydroeudistominy AT pkdubey anoxidativeamidationandheterocyclizationapproachforthesynthesisofbcarbolinesanddihydroeudistominy AT sureshbabumeruva oxidativeamidationandheterocyclizationapproachforthesynthesisofbcarbolinesanddihydroeudistominy AT akularaghunadh oxidativeamidationandheterocyclizationapproachforthesynthesisofbcarbolinesanddihydroeudistominy AT raghavendraraokamaraju oxidativeamidationandheterocyclizationapproachforthesynthesisofbcarbolinesanddihydroeudistominy AT uksyamkumar oxidativeamidationandheterocyclizationapproachforthesynthesisofbcarbolinesanddihydroeudistominy AT pkdubey oxidativeamidationandheterocyclizationapproachforthesynthesisofbcarbolinesanddihydroeudistominy |