Regioselective remote C5 cyanoalkoxylation and cyanoalkylation of 8-aminoquinolines with azobisisobutyronitrile

Chemical Communications : Chem Comm
Chunxia WenJizhen Li

Abstract

The efficient regioselective C-H cyanoalkoxylation and cyanoalkylation of 8-aminoquinoline derivatives at the C5 position have been achieved under O2 and N2 atmospheres, respectively. Using 2,2'-azobisisobutyronitrile (AIBN) as a radical precursor, the protocols afforded the corresponding products in moderate to good yields with broad substrate generality through Cu(OAc)2 or NiSO4 catalysis. Furthermore, the single electron transfer (SET) mechanism was proposed via a radical coupling pathway.

References

Oct 22, 2008·European Journal of Medicinal Chemistry·Nuno ValePaula Gomes
Aug 4, 2010·Journal of the American Chemical Society·Carl W LiskeyJohn F Hartwig
Mar 2, 2011·Journal of the American Chemical Society·Jaesung KwakSukbok Chang
Jun 12, 2013·Journal of the American Chemical Society·Alison M SuessShannon S Stahl
Feb 11, 2015·The Journal of Organic Chemistry·Fan TengJiang Cheng
Aug 4, 2015·Chemical Communications : Chem Comm·Guangwei RongXinfang Xu
Oct 7, 2015·Chemical Communications : Chem Comm·Hong-Wen LiangYe Wei
Dec 18, 2015·Bioorganic & Medicinal Chemistry Letters·Puneet P JainM G R Rajan
Jan 9, 2016·The Journal of Organic Chemistry·Jun WeiWei Zeng
Jan 21, 2016·Chemistry : a European Journal·Harekrishna SahooMahiuddin Baidya
Jan 6, 2017·Journal of Natural Products·Daniela Reimer, Chambers C Hughes
Apr 27, 2017·Chemical Reviews·Kei MurakamiKenichiro Itami

❮ Previous
Next ❯

Citations

May 26, 2021·The Journal of Organic Chemistry·Zengxin QinJizhen Li

❮ Previous
Next ❯

Methods Mentioned

BETA
X-ray

Related Concepts

Related Feeds

Alternative Complement Pathway

The Alternative Complement Pathway is part of the innate immune system, and activation generates membrane attack complexes that kill pathogenic cells. Discover the latest research on the Alternative Complement Pathway.