2-(methoxycarbonyl)ethyl as a removable N-protecting group: synthesis of indoloisoquinolinones by Pd(II)-catalyzed intramolecular diamination of alkynes

Organic Letters
Tu M HaJieping Zhu

Abstract

Pd(II)-catalyzed double cyclization of 1,2-diarylethynes bearing an N-methyl-N-[2-(methoxycarbonyl)ethyl]amino and an aminocarbonyl group at the ortho positions of the two aromatic rings afforded the tetracyclic N-[2-(methoxycarbonyl)ethyl]indoloisoquinolinones in good to excellent yields. The N-[2-(methoxycarbonyl)ethyl] group is readily removed under basic conditions (DBU, DMF, 120 °C) to afford the corresponding tetracycles with a free indolyl nitrogen in excellent yields. The 2-(methoxycarbonyl)ethyl as a removable N-protecting group is illustrated in other Pd(II)- and Pd(0)-catalyzed and selenium-mediated transformations.

References

May 19, 2005·Journal of the American Chemical Society·Grégory L J BarKevin I Booker-Milburn
Oct 20, 2005·Journal of the American Chemical Society·Jan StreuffKilian Muñiz
Jan 18, 2006·Organic Letters·Karl O Hessian, Bernard L Flynn
Jan 25, 2007·Journal of the American Chemical Society·Haifeng DuYian Shi
Jun 20, 2007·Chemical Society Reviews·Ana Minatti, Kilian Muñiz
Aug 19, 2007·Angewandte Chemie·Daniel Solé, Olga Serrano
Oct 31, 2008·Organic & Biomolecular Chemistry·Katrina H Jensen, Matthew S Sigman
Jan 23, 2009·The Journal of Organic Chemistry·Akio SaitoYuji Hanzawa
Feb 20, 2010·Journal of the American Chemical Society·Baoguo ZhaoYian Shi
Jul 31, 2010·Angewandte Chemie·Fatima C SequeiraSherry R Chemler
Sep 24, 2010·Angewandte Chemie·Alvaro IglesiasKilian Muñiz
Jul 31, 2012·Accounts of Chemical Research·Wanqing Wu, Huanfeng Jiang
Nov 8, 2014·Chemistry : a European Journal·Pavel Kočovský, Jan-E Bäckvall
Nov 18, 2014·Accounts of Chemical Research·Yingguang ZhuYian Shi

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Citations

Oct 2, 2015·Chemical Reviews·Kunbing OuyangZhenfeng Xi
May 7, 2016·Organic Letters·Hon Eong HoTienan Jin

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