Further exploration of the heterocyclic diversity accessible from the allylation chemistry of indigo
Diversity-directed synthesis based on the cascade allylation chemistry of indigo, with its embedded 2,2’-diindolic core, has resulted in rapid access to new examples of the hydroxy-8a,13-dihydroazepino[1,2-a:3,4-b']diindol-14(8H)-one skeleton in up to 51% yield. Additionally a derivative of the...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2015-04-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.11.54 |
| _version_ | 1818654838502719488 |
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| author | Alireza Shakoori John B. Bremner Mohammed K. Abdel-Hamid Anthony C. Willis Rachada Haritakun Paul A. Keller |
| author_facet | Alireza Shakoori John B. Bremner Mohammed K. Abdel-Hamid Anthony C. Willis Rachada Haritakun Paul A. Keller |
| author_sort | Alireza Shakoori |
| collection | DOAJ |
| description | Diversity-directed synthesis based on the cascade allylation chemistry of indigo, with its embedded 2,2’-diindolic core, has resulted in rapid access to new examples of the hydroxy-8a,13-dihydroazepino[1,2-a:3,4-b']diindol-14(8H)-one skeleton in up to 51% yield. Additionally a derivative of the novel bridged heterocycle 7,8-dihydro-6H-6,8a-epoxyazepino[1,2-a:3,4-b']diindol-14(13H)-one was produced when the olefin of the allylic substrate was terminally disubstituted. Further optimisation also produced viable one-pot syntheses of derivatives of the spiro(indoline-2,9'-pyrido[1,2-a]indol)-3-one (65%) and pyrido[1,2,3-s,t]indolo[1,2-a]azepino[3,4-b]indol-17-one (72%) heterocyclic systems. Ring-closing metathesis of the N,O-diallylic spiro structure and subsequent Claisen rearrangement gave rise to the new (1R,8aS,17aS)-rel-1,2-dihydro-1-vinyl-8H,17H,9H-benz[2',3']pyrrolizino[1',7a':2,3]pyrido[1,2-a]indole-8,17-(2H,9H)-dione heterocyclic system. |
| first_indexed | 2024-12-17T03:00:09Z |
| format | Article |
| id | doaj.art-12956ff9b5d9428eb84fd0fc028478c9 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-17T03:00:09Z |
| publishDate | 2015-04-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-12956ff9b5d9428eb84fd0fc028478c92022-12-21T22:06:06ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972015-04-0111148149210.3762/bjoc.11.541860-5397-11-54Further exploration of the heterocyclic diversity accessible from the allylation chemistry of indigoAlireza Shakoori0John B. Bremner1Mohammed K. Abdel-Hamid2Anthony C. Willis3Rachada Haritakun4Paul A. Keller5School of Chemistry, University of Wollongong, Wollongong, NSW, 2522, AustraliaSchool of Chemistry, University of Wollongong, Wollongong, NSW, 2522, AustraliaSchool of Chemistry, University of Wollongong, Wollongong, NSW, 2522, AustraliaSchool of Chemistry, The Australian National University, Canberra, ACT 0200, AustraliaNational Centre for Genetic Engineering and Biotechnology (BIOTEC), National Science and Technology Development Agency (NSTDA), 113 Phaholyothin Road, Klong1, Klong Luang, Pathumanthani 12120, ThailandSchool of Chemistry, University of Wollongong, Wollongong, NSW, 2522, AustraliaDiversity-directed synthesis based on the cascade allylation chemistry of indigo, with its embedded 2,2’-diindolic core, has resulted in rapid access to new examples of the hydroxy-8a,13-dihydroazepino[1,2-a:3,4-b']diindol-14(8H)-one skeleton in up to 51% yield. Additionally a derivative of the novel bridged heterocycle 7,8-dihydro-6H-6,8a-epoxyazepino[1,2-a:3,4-b']diindol-14(13H)-one was produced when the olefin of the allylic substrate was terminally disubstituted. Further optimisation also produced viable one-pot syntheses of derivatives of the spiro(indoline-2,9'-pyrido[1,2-a]indol)-3-one (65%) and pyrido[1,2,3-s,t]indolo[1,2-a]azepino[3,4-b]indol-17-one (72%) heterocyclic systems. Ring-closing metathesis of the N,O-diallylic spiro structure and subsequent Claisen rearrangement gave rise to the new (1R,8aS,17aS)-rel-1,2-dihydro-1-vinyl-8H,17H,9H-benz[2',3']pyrrolizino[1',7a':2,3]pyrido[1,2-a]indole-8,17-(2H,9H)-dione heterocyclic system.https://doi.org/10.3762/bjoc.11.54allylationcascade reactionsindigonitrogen heterocyclesrearrangement |
| spellingShingle | Alireza Shakoori John B. Bremner Mohammed K. Abdel-Hamid Anthony C. Willis Rachada Haritakun Paul A. Keller Further exploration of the heterocyclic diversity accessible from the allylation chemistry of indigo Beilstein Journal of Organic Chemistry allylation cascade reactions indigo nitrogen heterocycles rearrangement |
| title | Further exploration of the heterocyclic diversity accessible from the allylation chemistry of indigo |
| title_full | Further exploration of the heterocyclic diversity accessible from the allylation chemistry of indigo |
| title_fullStr | Further exploration of the heterocyclic diversity accessible from the allylation chemistry of indigo |
| title_full_unstemmed | Further exploration of the heterocyclic diversity accessible from the allylation chemistry of indigo |
| title_short | Further exploration of the heterocyclic diversity accessible from the allylation chemistry of indigo |
| title_sort | further exploration of the heterocyclic diversity accessible from the allylation chemistry of indigo |
| topic | allylation cascade reactions indigo nitrogen heterocycles rearrangement |
| url | https://doi.org/10.3762/bjoc.11.54 |
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