jo6b02100_si_001.pdf (3.6 MB)
Synthesis of Quinazolines from N,N′‑Disubstituted Amidines via I2/KI-Mediated Oxidative C–C Bond Formation
journal contribution
posted on 2016-09-27, 00:00 authored by Zhigang Lv, Bingnan Wang, Zhiyuan Hu, Yiming Zhou, Wenquan Yu, Junbiao ChangAn
I2/KI-promoted
oxidative C–C bond formation reaction from C(sp3)–H and C(sp2)–H
bonds has been used to construct quinazoline skeletons from N,N′-disubstituted amidines. The
required substrates are readily prepared from the corresponding acyl
chlorides, anilines, and alkyl/benzylamines by sequential amidation,
chlorination, and amination reactions. Under the optimal oxidative
cyclization conditions, all these amidines were conveniently transformed
into the expected products in moderate to good yields. This practical
and environmentally benign approach works well with crude amidine
intermediates and can also be carried out on a gram scale.