Microwave-assisted three-component domino reaction: Synthesis of indolodiazepinotriazoles
A microwave-assisted three-component protocol involving N-1 alkylation of 2-alkynylindoles with epichlorohydrin, ring opening of the epoxide with sodium azide, and an intramolecular Huisgen azide–internal alkyne 1,3-dipolar cycloaddition domino sequence has been described. The efficacy of the method...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2013-02-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.9.41 |
| _version_ | 1818556168718516224 |
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| author | Rajesh K. Arigela Sudhir K. Sharma Brijesh Kumar Bijoy Kundu |
| author_facet | Rajesh K. Arigela Sudhir K. Sharma Brijesh Kumar Bijoy Kundu |
| author_sort | Rajesh K. Arigela |
| collection | DOAJ |
| description | A microwave-assisted three-component protocol involving N-1 alkylation of 2-alkynylindoles with epichlorohydrin, ring opening of the epoxide with sodium azide, and an intramolecular Huisgen azide–internal alkyne 1,3-dipolar cycloaddition domino sequence has been described. The efficacy of the methodology has been demonstrated by treating various 2-alkynylindoles (aromatic/aliphatic) with epichlorohydrin and sodium azide furnishing annulated tetracyclic indolodiazepinotriazoles in satisfactory yields. |
| first_indexed | 2024-12-13T23:43:55Z |
| format | Article |
| id | doaj.art-a8a734cf569d4dbc9e4aa38900f6ba16 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-13T23:43:55Z |
| publishDate | 2013-02-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-a8a734cf569d4dbc9e4aa38900f6ba162022-12-21T23:27:05ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972013-02-019140140510.3762/bjoc.9.411860-5397-9-41Microwave-assisted three-component domino reaction: Synthesis of indolodiazepinotriazolesRajesh K. Arigela0Sudhir K. Sharma1Brijesh Kumar2Bijoy Kundu3Medicinal & Process Chemistry Division CSIR-Central Drug Research Institute, Lucknow-226001, IndiaMedicinal & Process Chemistry Division CSIR-Central Drug Research Institute, Lucknow-226001, IndiaSophisticated Analytical and Instrumental Facility, CSIR-Central Drug Research Institute, Lucknow-226001, IndiaMedicinal & Process Chemistry Division CSIR-Central Drug Research Institute, Lucknow-226001, IndiaA microwave-assisted three-component protocol involving N-1 alkylation of 2-alkynylindoles with epichlorohydrin, ring opening of the epoxide with sodium azide, and an intramolecular Huisgen azide–internal alkyne 1,3-dipolar cycloaddition domino sequence has been described. The efficacy of the methodology has been demonstrated by treating various 2-alkynylindoles (aromatic/aliphatic) with epichlorohydrin and sodium azide furnishing annulated tetracyclic indolodiazepinotriazoles in satisfactory yields.https://doi.org/10.3762/bjoc.9.412-alkynylindolesazides1,3-dipolar cycloadditiondomino reactionindolodiazepinotriazoles |
| spellingShingle | Rajesh K. Arigela Sudhir K. Sharma Brijesh Kumar Bijoy Kundu Microwave-assisted three-component domino reaction: Synthesis of indolodiazepinotriazoles Beilstein Journal of Organic Chemistry 2-alkynylindoles azides 1,3-dipolar cycloaddition domino reaction indolodiazepinotriazoles |
| title | Microwave-assisted three-component domino reaction: Synthesis of indolodiazepinotriazoles |
| title_full | Microwave-assisted three-component domino reaction: Synthesis of indolodiazepinotriazoles |
| title_fullStr | Microwave-assisted three-component domino reaction: Synthesis of indolodiazepinotriazoles |
| title_full_unstemmed | Microwave-assisted three-component domino reaction: Synthesis of indolodiazepinotriazoles |
| title_short | Microwave-assisted three-component domino reaction: Synthesis of indolodiazepinotriazoles |
| title_sort | microwave assisted three component domino reaction synthesis of indolodiazepinotriazoles |
| topic | 2-alkynylindoles azides 1,3-dipolar cycloaddition domino reaction indolodiazepinotriazoles |
| url | https://doi.org/10.3762/bjoc.9.41 |
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