Department Chemie, Ludwig-Maximilians-Universität München, Butenandtstrasse 5-13, Haus F, 81377 München (Germany).
Angew Chem Int Ed Engl. 2014 Jan 27;53(5):1430-4. doi: 10.1002/anie.201309217. Epub 2013 Dec 18.
A simple, flexible, and straightforward method for the functionalization of all the positions of the imidazole heterocycle through regioselective arylations, allylations, acylations, and additions to aldehydes is disclosed. Starting from the readily available key imidazole 1, highly functionalized imidazole derivatives have been synthesized in a regioselective manner from directed metalations and a sulfoxide/magnesium exchange. Moreover, the selective N3-alkylation followed by deprotection of N1 (trans-N-alkylation) allows the regioselective N-alkylation of complex imidazoles.
本文公开了一种通过区域选择性芳基化、烯丙基化、酰基化和加成到醛来对咪唑杂环的所有位置进行功能化的简单、灵活和直接的方法。从易得的关键咪唑 1 出发，通过定向金属化和亚砜/镁交换，以区域选择性方式合成了高度官能化的咪唑衍生物。此外，选择性的 N3-烷基化，然后脱保护 N1（反式 N-烷基化）允许对复杂咪唑进行区域选择性 N-烷基化。
