Cyclization Routes for the Synthesis of Functionalized Pyrano[2,3-b]indolones, Pyrazolo[3,4-b]indoles, and Furo[2,3-b]indoles

Arepalli Sateesh Kumar; Rajagopal Nagarajan

doi:10.1055/s-0032-1316870

Synthesis, Table of Contents

Synthesis 2013; 45(9): 1235-1246
DOI: 10.1055/s-0032-1316870

paper

Cyclization Routes for the Synthesis of Functionalized Pyrano[2,3-b]indolones, Pyrazolo[3,4-b]indoles, and Furo[2,3-b]indoles

Arepalli Sateesh Kumar

School of Chemistry, University of Hyderabad, Hyderabad 500 046, India Fax: +91(40)23012460 Email: rnsc@uohyd.ernet.in

,

Rajagopal Nagarajan*

School of Chemistry, University of Hyderabad, Hyderabad 500 046, India Fax: +91(40)23012460 Email: rnsc@uohyd.ernet.in

› Author Affiliations

Abstract

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Abstract

The synthesis of biologically active core structures containing pyrano[2,3-b]indol-2(9H)-ones, pyrano[2,3-b]indol-4(9H)-ones, pyrazolo[3,4-b]indoles, and furo[2,3-b]indoles are described. Pyrano[2,3-b]indol-2(9H)-ones are synthesized by three different metal-free syntheses (DCC, DMSO; CDI, DBU, CH₂Cl₂; or Mukaiyama’s reagent, Et₃N, MeCN) and pyrano[2,3-b]indol-4(9H)-ones are prepared by one-pot or two-step synthesis. Pyrazolo[3,4-b]indoles are synthesized by Fischer indole type cyclization and McMurry coupling is employed for the synthesis of furo[2,3-b]indoles. All these core structures are synthesized from simple, common 3-acetylindol-2-ols.

Key words

pyrano[2,3-b]indolones - pyrazolo[3,4-b]indoles - furo[2,3-b]indoles - Mukaiyama’s reagent - Fischer indole type cyclization

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References

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