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Further exploration of the heterocyclic diversity accessible from the allylation chemistry of indigo
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Metadata
Document Title
Further exploration of the heterocyclic diversity accessible from the allylation chemistry of indigo
Author
Shakoori A., Bremner J.B., Abdel-Hamid M.K., Willis A.C., Haritakun R., Keller P.A.
Name from Authors Collection
Affiliations
School of Chemistry, University of Wollongong, Wollongong, NSW 2522, Australia; School of Chemistry, Australian National University, Canberra, ACT 0200, Australia; National Centre for Genetic Engineering and Biotechnology (BIOTEC), National Science and Technology Development Agency (NSTDA), 113 Phaholyothin Road, Klong1, Klong Luang, Pathumanthani, 12120, Thailand
Type
Article
Source Title
Beilstein Journal of Organic Chemistry
ISSN
18605397
Year
2015
Volume
11
Page
481-492
Open Access
Gold, Green
Publisher
Beilstein-Institut Zur Forderung der Chemischen Wissenschaften
DOI
10.3762/bjoc.11.54
Abstract
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. © 2015 Shakoori et al; licensee Beilstein-Institut.
Keyword
Allylation | Cascade reactions | Indigo | Nitrogen heterocycles | Rearrangement
Industrial Classification
Knowledge Taxonomy Level 1
Knowledge Taxonomy Level 2
Knowledge Taxonomy Level 3
License
CC BY
Rights
Author
Publication Source
Scopus