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Further exploration of the heterocyclic diversity accessible from the allylation chemistry of indigo

Journal Article


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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.

Authors


  •   Shakoori, Alireza (external author)
  •   Bremner, John B.
  •   Abdel-Hamid, Mohammed K. (external author)
  •   Willis, Anthony C. (external author)
  •   Haritakun, Rachada (external author)
  •   Keller, Paul A.

Publication Date


  • 2015

Citation


  • Shakoori, A., Bremner, J. B., Abdel-Hamid, M. K., Willis, A. C., Haritakun, R. & Keller, P. A. (2015). Further exploration of the heterocyclic diversity accessible from the allylation chemistry of indigo. Beilstein Journal of Organic Chemistry, 11 481-492.

Scopus Eid


  • 2-s2.0-84930676646

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=4174&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/3151

Number Of Pages


  • 11

Start Page


  • 481

End Page


  • 492

Volume


  • 11

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.

Authors


  •   Shakoori, Alireza (external author)
  •   Bremner, John B.
  •   Abdel-Hamid, Mohammed K. (external author)
  •   Willis, Anthony C. (external author)
  •   Haritakun, Rachada (external author)
  •   Keller, Paul A.

Publication Date


  • 2015

Citation


  • Shakoori, A., Bremner, J. B., Abdel-Hamid, M. K., Willis, A. C., Haritakun, R. & Keller, P. A. (2015). Further exploration of the heterocyclic diversity accessible from the allylation chemistry of indigo. Beilstein Journal of Organic Chemistry, 11 481-492.

Scopus Eid


  • 2-s2.0-84930676646

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=4174&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/3151

Number Of Pages


  • 11

Start Page


  • 481

End Page


  • 492

Volume


  • 11