Iodine mediated intramolecular C2-amidative cyclization of indoles: a facile access to indole fused tetracycles

Organic & Biomolecular Chemistry
Sindhura BadigenchalaGovindasamy Sekar

Abstract

A novel and metal-free I2-mediated intramolecular C2 amidation of indoles under mild reaction conditions is developed. This methodology affords various indole fused tetracyclic compounds, such as benzo[4,5]imidazo[1,2-a]indoles by intramolecular C2 amidation of N-aryl substituted indoles. This C2 sulfonamidative cyclization also offers convenient access to indolo[2,3-b]indoles and dihydroindolo[2,3-b]quinoline from C3 aryl substituted indoles in good to excellent yields. Indolo[2,3-b]quinolines are also synthesized by the domino cyclization-detosylation-aromatization reaction sequence.

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Citations

Feb 25, 2017·The Journal of Organic Chemistry·Zhiyuan HuJunbiao Chang
Jul 7, 2017·The Journal of Organic Chemistry·Sindhura Badigenchala, Govindasamy Sekar
Aug 18, 2016·Chemical Communications : Chem Comm·Andreas Uwe MeyerBurkhard König
Aug 22, 2020·Organic & Biomolecular Chemistry·Chandrashekhar RapelliB V Subba Reddy
Feb 8, 2020·Topics in Current Chemistry·Bhaskar DekaPranjal K Baruah
Oct 31, 2019·The Journal of Organic Chemistry·Onnicha KhaikateChutima Kuhakarn
Dec 7, 2021·The Journal of Organic Chemistry·Matteo CorrieriGianfranco Favi

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