School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK.
J Org Chem. 2012 Feb 3;77(3):1217-32. doi: 10.1021/jo201866c. Epub 2011 Oct 14.
In a new variation on the Fischer indole synthesis, readily available haloarenes are converted into a wide range of indoles in just two steps by halogen-magnesium exchange and quenching with di-tert-butyl azodicarboxylate, followed by reaction with aldehydes or ketones under acidic conditions. The protocol, which is readily extended to the preparation of indole isosteres, 4- and 6-azaindoles and thienopyrroles, obviates the need to prepare potentially toxic aryl hydrazines, simultaneously avoiding undesirable anilines such as naphthylamines.
在 Fischer 吲哚合成的一种新变体中，通过卤素-镁交换和二特丁基偶氮二甲酸酯淬灭，很容易将易得的卤代芳烃转化为两种步骤，然后在酸性条件下与醛或酮反应，即可将其转化为广泛的吲哚。该方案可以很容易地扩展到吲哚类似物、4-和 6-氮杂吲哚以及噻吩并吡咯的制备，避免了制备潜在有毒的芳基腙的需要，同时避免了不希望有的苯胺，如萘胺。
