Department of Chemistry, University of Wisconsin, 1101 University Ave., Madison, WI 53706, USA.
Org Biomol Chem. 2019 Mar 20;17(12):3118-3128. doi: 10.1039/c9ob00073a.
An efficient four-step, six-transformation protocol was developed to afford bioactive N-alkyl- or N-arylamide (E)-arylamidines featuring strategic amidine C3 modifications which were inaccessible or low yielding by previous methods. This synthetic approach, exemplified with 24 amidines and requiring only a single purification, highlights a multicomponent Ugi-Mumm rearrangement to afford highly diversified quinazolinones which undergo regiospecific rearrangement to afford new amidines. The method extensively broadens the structural scope of this new class of trisubstituted amidines and demonstrates the tolerance of regional C3 amidine steric bulk, visualized with X-ray crystallographic analysis.
开发了一种高效的四步六转化方案，可提供具有战略性脒基 C3 修饰的生物活性 N-烷基或 N-芳基酰胺（E）-芳脒，这些修饰以前的方法无法获得或产率较低。该合成方法以 24 种脒为例，仅需一次纯化，突出了多组分 Ugi-Mumm 重排，可获得高度多样化的喹唑啉酮，这些喹唑啉酮可进行区域特异性重排，得到新的脒。该方法广泛扩展了这类新型三取代脒的结构范围，并通过 X 射线晶体学分析证明了区域 C3 脒位阻的耐受性。
